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3,4-METHYLENEDIOXYMETHAMPHETAMINE Latest Revision: August ...4-METHYLENEDIOXYMETHAMPHETA… ·...
Transcript of 3,4-METHYLENEDIOXYMETHAMPHETAMINE Latest Revision: August ...4-METHYLENEDIOXYMETHAMPHETA… ·...
34-METHYLENEDIOXYMETHAMPHETAMINE Latest Revision August 18 2005
1 SYNONYMS
CFR 34-Methylenedioxymethamphetamine (MDMA)
CAS Base 42542-10-9
dl-MDMA 69610-10-2
Hydrochloride 64057-70-1
dl-MDMA Hydrochloride 92279-84-0
Other Names N α-dimethyl-13-benzodioxole-5-ethanamine
N-methyl-34-methylenedioxyphenylisopropylamine
Methylenedioxymethamphetamine
MDM
MDMA
Ecstasy
E
XTC
Adam
Clarity
Elaine
Essence
Euphoria
2 CHEMICAL AND PHYSICAL DATA
21 CHEMICAL DATA
Form Chemical Formula Molecular Weight Melting Point (degC)
Base C11H15NO2 1932 Oil
Hydrochloride C11H15NO2middotHCl 2297 147-153
Phosphate C11H15NO2middotH3PO4 29124 184-185
22 SOLUBILITY
Form A C E H M W
Base S S S S I
Hydrochloride SS S I S S
Phosphate I I I I S VS
A = acetone C = chloroform E = ether H = hexane M = methanol and W = water VS = very soluble FS =
freely soluble S = soluble PS = sparingly soluble SS = slightly soluble VSS = very slightly soluble and I =
insoluble
3 SCREENING TECHNIQUES
31 COLOR TESTS
REAGENT COLOR PRODUCED
Marquis Purple to black
32 CRYSTAL TESTS
REAGENT CRYSTALS FORMED
Gold chloride in HOAc
Rosettes of various sizes with a rusty
color with high birefringence under
polarized light radiating from the
center outward down the arms
Feathery extensions from the arms
are parallel to each other preserved
on both sides of the arms
Platinic chloride in HOAc
Burr-like rosettes of various sizes
Radii from the center resemble pine
branches with fine needles Needles
have high birefringence under
polarized light
33 THIN LAYER CHROMATOGRAPHY
Visualization
Acidified potassium permanganate solution
COMPOUND
Relative Rf
System
TLC 5
System
TLC 6
34-methenedioxyethylamphetamine 13 18
34-methylenedioxyamphetamine 12 15
34-methylenedioxydimethylamphetamine 11 18
34-methylenedioxymethamphetamine 10 10
34 GAS CHROMATOGRAPHY
Method MDMA-GCS1
Instrument Gas chromatograph operated in split mode with FID
Column 5 phenyl95 methyl silicone 30 m x 025 mm x 025 microm film
thickness
Carrier gas Hydrogen at 20 mLmin
Temperatures Injector 260degC
Detector 270degC
Oven program
1) 90degC initial temperature for 10 min
2) Ramp to 295degC at 30degCmin
3) Hold final temperature for 26 min
Injection Parameters Split Ratio = 501 1 microL injected
Samples are to be dissolved in 41 chloroform methanol and filtered
COMPOUND RRT COMPOUND RRT
amphetamine 058 acetaminophen 118
methamphetamine 064 caffeine 127
safrole 076 methyl stearate 142
C14 085 cocaine 153
34-MDA 095 methyl eicosanoate 154
34-MDMA 100 (439 min) tetraphenylethylene 169
34-MDEA 104 heroin 180
34-MDDMA 106
Method MDMA-GCS2
Instrument Gas Chromatograph operated in split mode with FID
Column 50 phenyl50 methyl silicone 30 m x 025 mm x 025 microm film
thickness
Carrier gas Hydrogen at 20 mLmin
Temperatures Injector 260degC
Detector 270degC
Oven program
1) 90degC initial temperature for 10 min
2) Ramp to 295degC at 30degmin
3) Hold final temperature for 26 min
Injection Parameters Split Ratio = 501 1 microL injected
Samples are to be dissolved in 41 chloroform methanol and filtered
COMPOUND RRT COMPOUND RRT
amphetamine 060 acetaminophen 127
methamphetamine 064 caffeine 134
safrole 078 methyl stearate 126
C14 067 cocaine 153
34-MDA 097 methyl eicosanoate 137
34-MDMA 100 (499 min) tetraphenylethylene 172
34-MDEA 102 heroin 197
34-MDDMA 104
Method MDMA-GCS3
Instrument Gas chromatograph operated in split mode with FID
Column 5 phenyl95 methyl silicone 5 m x 025 mm x 025 microm film
thickness
Carrier gas Hydrogen
1) Initial pressure of 25 psi for 010 min
2) Ramp to 50 psi at 341 psimin
3) Hold final pressure for 077 min
Temperature Injector 260degC
Detector 270degC
Oven program
1) 90degC initial temperature
2) Ramp to 100degC at 10degmin
3) Hold final temperature for 060 min
Injection Parameters Split Ratio = 501 1 microL injected
EZFlash Parameters
1) Time 0 s = 100oC
2) Time 6 s = 110oC
3) Time 50 s = 310oC
4) Time 96 s = 310oC
Samples are to be dissolved in 41 chloroform methanol and filtered
COMPOUND RRT COMPOUND RRT
amphetamine 070 acetaminophen 114
methamphetamine 074 caffeine 122
safrole 082 methyl stearate 123
C14 088 cocaine 144
34-MDA 096 methyl eicosanoate 134
34-MDMA 100 (499 min) tetraphenylethylene 162
34-MDEA 103 heroin 180
34-MDDMA 104
Method MDMA-GCS4
Instrument Gas chromatograph operated in split mode with FID
Column 1 phenyl99 methyl silicone 30 m x 025 mm x 025 microm film
thickness
Carrier gas Hydrogen at 20 mLmin
Temperature Injector 260degC
Detector 270degC
Oven program
1) 90degC initial temperature for 10 min
2) Ramp to 295degC at 30 degreesmin
3) Hold final temperature for 26 min
Injection Parameters Split Ratio = 501 1 microL injected
COMPOUND RRT COMPOUND RRT
amphetamine 053 acetaminophen 119
methamphetamine 165 caffeine 128
safrole 072 methyl stearate 153
C14 091 cocaine 160
34-MDA 094 methyl eicosanoate 167
34-MDMA 100 (436 min) tetraphenylethylene 178
34-MDEA 105 heroin 189
34-MDDMA 108
4 SEPARATION TECHNIQUES
MDMA base hydrochloride or phosphate can be separated from the matrix by solvent extraction using
the solubility data found in Section 22
5 QUANTITATIVE PROCEDURES
51 GAS CHROMATOGRAPHY
Method MDMA-GCQ1
Internal Standard Stock Solution
10 mgmL n-butylamphetamine HCl in chloroform
Standard Solution Preparation
Prepare a standard solution of MDMA HCl at 04 mgmL in chloroform
Sample Preparation
Accurately weigh out 50 mg of sample into a 25 mL volumetric flask and dilute with water to the mark Take a
2 mL aliquot of the solution add 3 mL of IS and 2-3 mL of 05 M KOH Shake Separate layers and extract
twice more with 2-3 mL each time of chloroform Combine fractions dry over sodium sulfate and dilute to
total volume of 10 mL Treat the standard in the same fashion as the sample prior to analysis
Instrument Gas chromatograph operated in split mode with FID
Column DB-1 30 m x 025 mm x 025 microm film thickness
Carrier gas Hydrogen at 13 mLmin
Make-Up gas Nitrogen at 400 mLmin
Temperatures Injector 230degC
Detector 280degC
Oven Program
1) 150degC initial temperature 2 min
2) Ramp to 190degC at 5degmin
3) Hold final temperature for 10 min
Injection Parameters Split Ratio = 201 1 microL injected
Typical Retention Time 34-MDMA 510 min
n-butylamphetamine HCl 392 min
Linear Range 006 mgmL to 20 mgmL
Repeatability RSD less than 20
Correlation Coefficient 09998
Accuracy Error less than 5
COMPOUND RRT COMPOUND RRT COMPOUND RRT
methylbenzylamine 035 methyl paraben 077 caffeine 186
P-2-P 038 salicylamide 077 antipyrine 200
amphetamine 039 penicillin 078 benzphetamine 204
nicotinic acid 042 phenmetrazine 081 diphenhydramine 214
phentermine 042 MDP-2-P 084 aminopyrine 226
methamphetamine 044 phendimetrazine 086 doxylamine 231
fenfluramine 048 MDA 087 palmitic acid 245
ethylamphetamine 049 MDMA 100 (51 min) phthalic acid 245
dimethylamphetamine 050 aminorex 105 dipyrone 251
safrole 055 methyl aminorex 105 procaine 266
salicylic acid 056 MDEA 113 eicosane 267
cathine 059 ibuprofen 124 dextromethorphan 312
phenylpropanolamine 059 MBDB 126 strychnine 317
methcathinone 060 hexadecane 128 phenyl-2-naphthalene 327
nicotinamide 062 glycerol glycolate 130 amitriptyline 334
chlorpheniramine 065 acetaminophen 135 scopolamine 371
chloroephedrine 066 MMDA 138 tetracosane 407
pseudoephedrine 066 phenacetin 141 chlordiazepoxide 431
ephedrine 068 chloro-MDMA 149 quinine 523
butylamphetamine 077 methylphenidate 163
52 HIGH PERFORMANCE LIQUID CHROMATOGRAPHY
Method MDMA-LCQ1
Standard Solution Preparation
Prepare a standard solution of MDMA at approximately 05 mgmL using water buffer or methanol
Sample Preparation
Accurately weigh an amount of sample into an appropriate volumetric or Erlenmeyer flask and dilute so
that the final MDMA concentration is approximately that of the standard solution
Instrument High performance liquid chromatograph equipped with diode array
Column 5 microm Phenomenex Luna 150 mm x 32 mm at 35C
Detector UV 210 nm
Flow 10 mLmin
Injection Volume 5 microL
Buffer 4000 mL distilled water 225 mL phosphoric acid adjust to pH 22-
23 with triethanolamine (approx 22 mL)
Mobile Phase Bufferacetonitrile 9010
Typical Retention Time 34-MDMA 1054 min
Linear Range 005 mgmL ndash 2 mgmL
Repeatability RSD less than 05
Correlation Coefficient 09999
Accuracy Error less than 5
COMPOUND RRT COMPOUND RRT
phenylpropanolamine 060 methyl aminorex 101
methyl benzylamine 062 phentermine 102
cathine 063 chloroephedrine 103
doxylamine 069 ethylamphetamine 105
dipyrone 070 MDP-2-P 105
ephedrine 072 lidocaine 107
methcathinone 073 caffeine q
pseudoephedrine 073 MDEA 113
amphetamine 084 phenyl-2-naphthalene 113
theophylline 087 phthalic acid 113
methapyrilene 089 strychnine 114
phenmetrazine 089 MMDA 117
methamphetamine 091 MBDB 125
phendimetrazine 091 salicylamide 127
COMPOUND RRT COMPOUND RRT
scopolamine 092 acetaminophen 129
MDA 093 chloro-MDMA 137
quinine 096 methylphenidate 138
saccharin 096 glycerol glycolate 148
dimethylamphetamine 097 chlorpheniramine 155
MDMA 100 (1054 min) aspirin 181
chlordiazepoxide 187
53 CAPILLARY ELECTROPHORESIS
Method MDMA-CEQ1
Internal Standard Stock Solution
050 mgmL n-butylamphetamine in 50 mM sodium phosphate at pH 70
Standard Solution Preparation
Accurately weigh and prepare a standard solution of 34-methylenedioxymethamphetamine hydrochloride at
approximately 08 mgmL using the internal standard stock solution
Sample Preparation
Accurately weigh an amount of sample into a volumetric flask and dilute with internal standard stock solution
If necessary dilute the sample so the final concentration approximates the standard concentration or falls within
the linear range Filter sample with 045-micron filter
Mode Cyclodextrin system analysis
Column 49 cm x 52 microm fused silica capillary
Run Buffer 10 mM gamma-highly sulfated cyclodextrin in 50 mM sodium phosphate
at pH 70
Detector UV 210 nm
Voltage 12 kV
Temperature 30degC air cooled
Injection 1 sec hydrodynamic at 50 mbars
Run Time 17 min
Rinse Time 20 min
Linear Range 002 - 100 mgmL
Repeatability RSD of area less than 15
Correlation Coefficient 0999
Accuracy Error less than 5
COMPOUND RRT COMPOUND RRT
d-methamphetamine 066 l-pseudoephedrine 098
d-ephedrine 074 MDMA 100 (1104 min)
MDA 080 l-ephedrine 109
cathine 085 MDEA 112
l-methamphetamine 089 MDMA 119
d-amphetamine 094 l-norephedrine 132
d-norephedrine 094 l-amphetamine 134
d-pseudoephedrine 097 MDA 136
MDEA 149
Method MDMA-CEQ2
Internal Standard Stock Solution
10 mgmL n-butylamphetamine in 38 mM phosphate buffer (pH 25)
Standard Solution Preparation
Weigh an appropriate amount of standard 34-MDMA HCl into a volumetric flask to obtain a final
concentration of approximately 008 mgmL Pipette appropriate amount of internal standard solution to obtain
a final concentration of 01 mgmL Dilute to volume with injection solvent Filter approximately 10 mL of
solution with regenerated cellulose 045 microm 25 mm filter into a 20 mL glass vial (Agilent part number 5182-
0567) Make sure there are no air bubbles on bottom of glass vial Cap vial with polypropylene cap (Agilent
part number 5182-9697)
Sample Preparation
Weigh an appropriate amount of sample into a volumetric flask so that the final phenethylamine concentration
is approximately that of the standard solution Pipette appropriate amount of internal standard solution to obtain
a final concentration of 01 mgmL Dilute to volume with injection solvent Sonicate for 15 minutes Filter
approximately 10 mL of solution with regenerated cellulose 045 microm 25 mm filter into a 20 mL glass vial
(Agilent part number 5182-0567) Make sure there are no air bubbles on bottom of glass vial Cap vial with
polypropylene cap (Agilent part number 5182-9697)
Mode HP 3D instrument operated in CE mode
Coated Capillary Mode
Column 50 microm id x 322 cm (237 cm length to detector)
Run Buffer Celixir Reagent B pH 25 (MicroSolv CE)
Detector UV 195 nm
Voltage 10 kV
Temperature 15degC
Injection 50 mbar x 2 s followed by water at 35 mbar
Run Time 6 min
Rinse Time 2 min
Linear Range 002 - 100 mgmL
Repeatability RSD lt16
Correlation Coefficient 10
Accuracy Error less than 32
COMPOUND RRT COMPOUND RRT
doxylamine 0765 ephedrine 0932
chlorpheniramine 0784 phenylephrine 0951
quinine 0804 MDEA 0961
-phenethylamine 0807 ketamine 0962
COMPOUND RRT COMPOUND RRT
chlorquinine 0812 phenyltoxolamine 0971
nicotinamide 0836 n-butylamphetamine 10(46 min)
amphetamine 0868 dextromethorphan 100
methamphetamine 0883 lidocaine 103
procaine 0883 benzocaine 125
MDA 0900 acetaminophen 211
norpseudoephedrine 0906 caffeine 214
MDMA 0914 guaifenesin 214
norephedrine 0917 P2P 224
pseudoephedrine 0919 DMSO (neutral marker) 240
tetracaine 0927 aspirin 271
54 NUCLEAR MAGNETIC RESONANCE
Method MDMA-NMR1
Solvents Deuterium Oxide (D2O) containing DSS or TSP for 0 PPM reference
Internal Standard Stock Solution (ISSS) 5 mgmL Maleic Acid (accurately weighed) in deuterium oxide (D2O)
containing DSS or TSP for 0 ppm reference
Sample Preparation Accurately weigh an amount of sample usually 10-30 mg into a capped test tube and
accurately add a volume normally 10 mL of the ISSS Vortex the sample for several seconds If insolubles
are present add 10 mL D2O (not containing maleic acid or the reference compound) vortex and sonicate 15
minutes Vortex the sample and filter if necessary Place in NMR sample tube
Instrument Varian Mercury 400 MHz with proton detection probe NMR
Spectrometer
Pulse Width 10 micros or 90deg(whichever is less)
Spectral Width (SW) at least containing ndash3 ppm through 13 ppm
Number of Scans multiple of 4 (greater to enhance signal to noise (SN))
Delay between Pulses 45 s
Shimming automatic gradient shimming of Z1-4 shims
Total run timesample 6 min (NT=4) -14 min (NT=16)
Uniformity within spectral width 03 RSD (-06 to 114 PPM)
Run Time 6 min
Linear Range 06 mgmL-60 mgmL
Repeatability lt 4
Correlation Coefficient 10
Accuracy lt 3
Compound MW Solvent Internal
Standard
Solubility
(mgmL)
Signals used for
quantitation
(position in ppm
with number of
protons) Signals in
bold and underlined
are preferred if
other numbers
present
Decompos
ition rate
(hour)
MDMA HCl 22971 D2O maleic
acid gt30
67-69 (m)(3) 60
(s)(2) 35 (sextet)(1)
30dd(1) 28dd(1)
27 (s)(3) 13 (d)(3)
lt01
MDMA
phosphate 29124 D2O
maleic
acid gt19
67-69 (m)(3) 60
(s)(2) 35 (sextet)(1)
30dd(1) 28dd(1)
27 (s)(3) 13 (d)(3)
lt01
6 QUALITATIVE DATA
See spectra on the following pages for FT-IR Vapor Phase IR FT-Raman Mass Spectrometry and Nuclear
Magnetic Resonance
7 REFERENCES
Coates J and Reffner J Visualization of Micro-ATR Infrared Spectroscopy Spectroscopy Vol 14 4
April 1999
Clarke EGC Isolation and Identification of Drugs 2nd Edition The Pharmaceutical Press 1986
Galichat Laurent Y Clarkersquos Analysis of Drugs and Poisons Volume 2 p 1256 Pharmaceutical Press 2004
Budavari S The Merck Index 13th Edition Merck and Co Inc 2001
8 ADDITIONAL RESOURCES
Forendex
Wikipedia
FTIR (KBr) 34-Methylenedioxymethamphetamine Hydrochloride
50 scans 1 nm resolution 5 mg150 mg
FTIR (diamond ATR 3 bounce) 34-Mehtylenedioxymethamphetamine Base
FTIR (1 bounce ATR) MDMA phosphate
32 scans resolution 4 cm-1
IR (Vapor Phase) 34-Methylenedioxymethamphetamine Lot A150B
2 mgmL in CH3OH
FT-RAMAN 34-Methylenedioxymethamphetamine Base
Extracted from MDMA HCl Lot A150B 32 scans 4 cm-1
resolution
FT-RAMAN 34-Methylenedioxymethamphetamine HCl
Lot A150B 32 scans 4 cm-1
resolution
19
48
26
09
34
79
36
61
45
675
34
5
60
41
66
74
71
46
77
21
81
27
88
74
10
39
6
10
97
8
11
54
7
12
47
1
12
89
61
33
69
13
60
5
13
98
01
44
19
15
02
5
16
09
41
62
88
27
93
7
29
32
72
96
79
30
37
23
07
03
33
30
5
00
05
10
15
20
25
30
35
40
45
50
55
60
65
70
75
80In
t
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
19
28
25
19
34
08
37
96
41
00
44
79
47
83
53
40
60
51
63
26
71
61
77
55
81
29
88
63
92
73
10
37
9
10
80
1
11
98
1
12
47
9
13
04
51
33
12
13
69
6
14
01
21
44
32
15
07
2
16
09
51
63
15
27
81
1
28
63
62
90
37
29
33
7
29
69
22
99
14
30
58
4
2
4
6
8
10
12
14
16
18
20
22
24
26
Int
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
FT-RAMAN 34-Methylenedioxymethamphetamine Phosphate Lot 2 TDM-275-01
32 scans 4 cm-1
resolution
Mass Spectrometry (EI) 34-Methylenedioxymethamphetamine
10
66
20
68
25
61
34
42
42
41
47
36
53
98
60
38
63
98
71
41
77
72
81
18
83
67
90
70
10
11
8
10
74
91
10
57
12
01
61
22
83
12
55
1
13
53
1
13
99
3
14
42
0
14
91
7
16
07
81
63
02
23
54
027
98
3
29
40
62
96
43
30
40
83
06
97
00
05
10
15
20
25
30
35
40
45
50
55
Int
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
Mass Spectrometry (CI) 34-Methylenedioxymethamphetamine
1H NMR MDMA base in CDCl3 with TMS 400 MHz
Extracted from MDMA HCl ndash Lot A150B
ppm 673 (d J=783 Hz 1 H) 668 (d J=117 Hz 1 H) 663 (dd J=783 117 Hz 1 H) 592 (s 2 H) 267 -
278 (ddq J=720 630 630 630 630 Hz 1 H) 261 (dd J=1350 724 Hz 1 H) 254 (dd J=1330 626
Hz 1 H) 239 (s 3 H) 104 (d J=626 Hz 3 H)
13C NMR MDMA Base
Extracted from MDMA HCl ndash Lot A 150B
1H NMR MDMA Phosphate in D2O with TSP 400 MHz
Lot 2 TDM-275-01
ppm 688 - 692 (d J=800 Hz 1 H) 686 (d J=137 Hz 1 H) 680 (dd J=800 140 Hz 1 H) 598 (s 2 H)
344 - 355 (ddq J=750 670 670 670 650 Hz 1 H) 299 (dd J=1390 650 Hz 1 H) 285 (dd J=1390
760 Hz 1 H) 270 (s 3 H) 128 (d J=665 Hz 3 H)
13C NMR MDMA Phosphate in D2O with TSP Lot 2 TDM-275-01
1H NMR MDMA Phosphate in CD3OD with TMS Lot 2 TDM-275-01
400 MHz
ppm 679 (d J=098 Hz 1 H) 678 (d J=802 Hz 1 H) 673 (dd J=800 120 Hz 1 H)
593 (s 2 H) 329 - 340 (m 1 H) 308 (dd J=1350 509 Hz 1 H) 269 (s 3 H) 267 (dd
J=1330 960 Hz 1 H) 122 (d J=646 Hz 3 H)
1H NMR MDMA HCl Lot A150B
with maleic acid as internal standard in D2O with TSP 400 MHz
ppm 688 (d J=792 Hz 1 H) 684 (d J=166 Hz 1 H) 676 - 681 (dd J=790 180 Hz 1
H) 597 (s 2 H) 341 - 354 (ddq J=770 670 670 670 650 Hz 1 H) 293 - 302 (dd
J=1400 650 Hz 1 H) 283 (dd J=1400 770 Hz 1 H) 270 (s 3 H) 127 (d J=665 Hz
3 H) Maleic acid 640 (s 2H)
1H NMR MDMA base in CD3OD with TMS
Extracted from MDMA HCl ndash Lot A150B 400 MHz
ppm 669 - 674 (d J=783 Hz 1 H) 667 (d J=137 Hz 1 H) 662 (dd J=780 140 Hz 1
H) 588 (s 2 H) 265 - 276 (m 2 H) 244 (dd J=1530 940 Hz 1 H) 234 (s 3 H) 100
(d J=606 Hz 3 H)
1H NMR MDMA HCl in CD3OD Lot A150B
400 MHz
ppm 680 (d J=160 Hz 1 H) 679 (d J=802 Hz 1 H) 674 (dd J=802 156 Hz 1 H) 593 (s 2 H) 336 -
348 (ddq J=940 650 650 650 530 Hz 1 H) 308 (dd J=1350 528 Hz 1 H) 271 (dd J=1330 940
Hz 1 H) 125 (d J=646 Hz 3 H)
13C NMR MDMA HCl in CD3OD Lot A150B
Optical isomers standards for these compounds were unavailable
No Data Available
22 SOLUBILITY
Form A C E H M W
Base S S S S I
Hydrochloride SS S I S S
Phosphate I I I I S VS
A = acetone C = chloroform E = ether H = hexane M = methanol and W = water VS = very soluble FS =
freely soluble S = soluble PS = sparingly soluble SS = slightly soluble VSS = very slightly soluble and I =
insoluble
3 SCREENING TECHNIQUES
31 COLOR TESTS
REAGENT COLOR PRODUCED
Marquis Purple to black
32 CRYSTAL TESTS
REAGENT CRYSTALS FORMED
Gold chloride in HOAc
Rosettes of various sizes with a rusty
color with high birefringence under
polarized light radiating from the
center outward down the arms
Feathery extensions from the arms
are parallel to each other preserved
on both sides of the arms
Platinic chloride in HOAc
Burr-like rosettes of various sizes
Radii from the center resemble pine
branches with fine needles Needles
have high birefringence under
polarized light
33 THIN LAYER CHROMATOGRAPHY
Visualization
Acidified potassium permanganate solution
COMPOUND
Relative Rf
System
TLC 5
System
TLC 6
34-methenedioxyethylamphetamine 13 18
34-methylenedioxyamphetamine 12 15
34-methylenedioxydimethylamphetamine 11 18
34-methylenedioxymethamphetamine 10 10
34 GAS CHROMATOGRAPHY
Method MDMA-GCS1
Instrument Gas chromatograph operated in split mode with FID
Column 5 phenyl95 methyl silicone 30 m x 025 mm x 025 microm film
thickness
Carrier gas Hydrogen at 20 mLmin
Temperatures Injector 260degC
Detector 270degC
Oven program
1) 90degC initial temperature for 10 min
2) Ramp to 295degC at 30degCmin
3) Hold final temperature for 26 min
Injection Parameters Split Ratio = 501 1 microL injected
Samples are to be dissolved in 41 chloroform methanol and filtered
COMPOUND RRT COMPOUND RRT
amphetamine 058 acetaminophen 118
methamphetamine 064 caffeine 127
safrole 076 methyl stearate 142
C14 085 cocaine 153
34-MDA 095 methyl eicosanoate 154
34-MDMA 100 (439 min) tetraphenylethylene 169
34-MDEA 104 heroin 180
34-MDDMA 106
Method MDMA-GCS2
Instrument Gas Chromatograph operated in split mode with FID
Column 50 phenyl50 methyl silicone 30 m x 025 mm x 025 microm film
thickness
Carrier gas Hydrogen at 20 mLmin
Temperatures Injector 260degC
Detector 270degC
Oven program
1) 90degC initial temperature for 10 min
2) Ramp to 295degC at 30degmin
3) Hold final temperature for 26 min
Injection Parameters Split Ratio = 501 1 microL injected
Samples are to be dissolved in 41 chloroform methanol and filtered
COMPOUND RRT COMPOUND RRT
amphetamine 060 acetaminophen 127
methamphetamine 064 caffeine 134
safrole 078 methyl stearate 126
C14 067 cocaine 153
34-MDA 097 methyl eicosanoate 137
34-MDMA 100 (499 min) tetraphenylethylene 172
34-MDEA 102 heroin 197
34-MDDMA 104
Method MDMA-GCS3
Instrument Gas chromatograph operated in split mode with FID
Column 5 phenyl95 methyl silicone 5 m x 025 mm x 025 microm film
thickness
Carrier gas Hydrogen
1) Initial pressure of 25 psi for 010 min
2) Ramp to 50 psi at 341 psimin
3) Hold final pressure for 077 min
Temperature Injector 260degC
Detector 270degC
Oven program
1) 90degC initial temperature
2) Ramp to 100degC at 10degmin
3) Hold final temperature for 060 min
Injection Parameters Split Ratio = 501 1 microL injected
EZFlash Parameters
1) Time 0 s = 100oC
2) Time 6 s = 110oC
3) Time 50 s = 310oC
4) Time 96 s = 310oC
Samples are to be dissolved in 41 chloroform methanol and filtered
COMPOUND RRT COMPOUND RRT
amphetamine 070 acetaminophen 114
methamphetamine 074 caffeine 122
safrole 082 methyl stearate 123
C14 088 cocaine 144
34-MDA 096 methyl eicosanoate 134
34-MDMA 100 (499 min) tetraphenylethylene 162
34-MDEA 103 heroin 180
34-MDDMA 104
Method MDMA-GCS4
Instrument Gas chromatograph operated in split mode with FID
Column 1 phenyl99 methyl silicone 30 m x 025 mm x 025 microm film
thickness
Carrier gas Hydrogen at 20 mLmin
Temperature Injector 260degC
Detector 270degC
Oven program
1) 90degC initial temperature for 10 min
2) Ramp to 295degC at 30 degreesmin
3) Hold final temperature for 26 min
Injection Parameters Split Ratio = 501 1 microL injected
COMPOUND RRT COMPOUND RRT
amphetamine 053 acetaminophen 119
methamphetamine 165 caffeine 128
safrole 072 methyl stearate 153
C14 091 cocaine 160
34-MDA 094 methyl eicosanoate 167
34-MDMA 100 (436 min) tetraphenylethylene 178
34-MDEA 105 heroin 189
34-MDDMA 108
4 SEPARATION TECHNIQUES
MDMA base hydrochloride or phosphate can be separated from the matrix by solvent extraction using
the solubility data found in Section 22
5 QUANTITATIVE PROCEDURES
51 GAS CHROMATOGRAPHY
Method MDMA-GCQ1
Internal Standard Stock Solution
10 mgmL n-butylamphetamine HCl in chloroform
Standard Solution Preparation
Prepare a standard solution of MDMA HCl at 04 mgmL in chloroform
Sample Preparation
Accurately weigh out 50 mg of sample into a 25 mL volumetric flask and dilute with water to the mark Take a
2 mL aliquot of the solution add 3 mL of IS and 2-3 mL of 05 M KOH Shake Separate layers and extract
twice more with 2-3 mL each time of chloroform Combine fractions dry over sodium sulfate and dilute to
total volume of 10 mL Treat the standard in the same fashion as the sample prior to analysis
Instrument Gas chromatograph operated in split mode with FID
Column DB-1 30 m x 025 mm x 025 microm film thickness
Carrier gas Hydrogen at 13 mLmin
Make-Up gas Nitrogen at 400 mLmin
Temperatures Injector 230degC
Detector 280degC
Oven Program
1) 150degC initial temperature 2 min
2) Ramp to 190degC at 5degmin
3) Hold final temperature for 10 min
Injection Parameters Split Ratio = 201 1 microL injected
Typical Retention Time 34-MDMA 510 min
n-butylamphetamine HCl 392 min
Linear Range 006 mgmL to 20 mgmL
Repeatability RSD less than 20
Correlation Coefficient 09998
Accuracy Error less than 5
COMPOUND RRT COMPOUND RRT COMPOUND RRT
methylbenzylamine 035 methyl paraben 077 caffeine 186
P-2-P 038 salicylamide 077 antipyrine 200
amphetamine 039 penicillin 078 benzphetamine 204
nicotinic acid 042 phenmetrazine 081 diphenhydramine 214
phentermine 042 MDP-2-P 084 aminopyrine 226
methamphetamine 044 phendimetrazine 086 doxylamine 231
fenfluramine 048 MDA 087 palmitic acid 245
ethylamphetamine 049 MDMA 100 (51 min) phthalic acid 245
dimethylamphetamine 050 aminorex 105 dipyrone 251
safrole 055 methyl aminorex 105 procaine 266
salicylic acid 056 MDEA 113 eicosane 267
cathine 059 ibuprofen 124 dextromethorphan 312
phenylpropanolamine 059 MBDB 126 strychnine 317
methcathinone 060 hexadecane 128 phenyl-2-naphthalene 327
nicotinamide 062 glycerol glycolate 130 amitriptyline 334
chlorpheniramine 065 acetaminophen 135 scopolamine 371
chloroephedrine 066 MMDA 138 tetracosane 407
pseudoephedrine 066 phenacetin 141 chlordiazepoxide 431
ephedrine 068 chloro-MDMA 149 quinine 523
butylamphetamine 077 methylphenidate 163
52 HIGH PERFORMANCE LIQUID CHROMATOGRAPHY
Method MDMA-LCQ1
Standard Solution Preparation
Prepare a standard solution of MDMA at approximately 05 mgmL using water buffer or methanol
Sample Preparation
Accurately weigh an amount of sample into an appropriate volumetric or Erlenmeyer flask and dilute so
that the final MDMA concentration is approximately that of the standard solution
Instrument High performance liquid chromatograph equipped with diode array
Column 5 microm Phenomenex Luna 150 mm x 32 mm at 35C
Detector UV 210 nm
Flow 10 mLmin
Injection Volume 5 microL
Buffer 4000 mL distilled water 225 mL phosphoric acid adjust to pH 22-
23 with triethanolamine (approx 22 mL)
Mobile Phase Bufferacetonitrile 9010
Typical Retention Time 34-MDMA 1054 min
Linear Range 005 mgmL ndash 2 mgmL
Repeatability RSD less than 05
Correlation Coefficient 09999
Accuracy Error less than 5
COMPOUND RRT COMPOUND RRT
phenylpropanolamine 060 methyl aminorex 101
methyl benzylamine 062 phentermine 102
cathine 063 chloroephedrine 103
doxylamine 069 ethylamphetamine 105
dipyrone 070 MDP-2-P 105
ephedrine 072 lidocaine 107
methcathinone 073 caffeine q
pseudoephedrine 073 MDEA 113
amphetamine 084 phenyl-2-naphthalene 113
theophylline 087 phthalic acid 113
methapyrilene 089 strychnine 114
phenmetrazine 089 MMDA 117
methamphetamine 091 MBDB 125
phendimetrazine 091 salicylamide 127
COMPOUND RRT COMPOUND RRT
scopolamine 092 acetaminophen 129
MDA 093 chloro-MDMA 137
quinine 096 methylphenidate 138
saccharin 096 glycerol glycolate 148
dimethylamphetamine 097 chlorpheniramine 155
MDMA 100 (1054 min) aspirin 181
chlordiazepoxide 187
53 CAPILLARY ELECTROPHORESIS
Method MDMA-CEQ1
Internal Standard Stock Solution
050 mgmL n-butylamphetamine in 50 mM sodium phosphate at pH 70
Standard Solution Preparation
Accurately weigh and prepare a standard solution of 34-methylenedioxymethamphetamine hydrochloride at
approximately 08 mgmL using the internal standard stock solution
Sample Preparation
Accurately weigh an amount of sample into a volumetric flask and dilute with internal standard stock solution
If necessary dilute the sample so the final concentration approximates the standard concentration or falls within
the linear range Filter sample with 045-micron filter
Mode Cyclodextrin system analysis
Column 49 cm x 52 microm fused silica capillary
Run Buffer 10 mM gamma-highly sulfated cyclodextrin in 50 mM sodium phosphate
at pH 70
Detector UV 210 nm
Voltage 12 kV
Temperature 30degC air cooled
Injection 1 sec hydrodynamic at 50 mbars
Run Time 17 min
Rinse Time 20 min
Linear Range 002 - 100 mgmL
Repeatability RSD of area less than 15
Correlation Coefficient 0999
Accuracy Error less than 5
COMPOUND RRT COMPOUND RRT
d-methamphetamine 066 l-pseudoephedrine 098
d-ephedrine 074 MDMA 100 (1104 min)
MDA 080 l-ephedrine 109
cathine 085 MDEA 112
l-methamphetamine 089 MDMA 119
d-amphetamine 094 l-norephedrine 132
d-norephedrine 094 l-amphetamine 134
d-pseudoephedrine 097 MDA 136
MDEA 149
Method MDMA-CEQ2
Internal Standard Stock Solution
10 mgmL n-butylamphetamine in 38 mM phosphate buffer (pH 25)
Standard Solution Preparation
Weigh an appropriate amount of standard 34-MDMA HCl into a volumetric flask to obtain a final
concentration of approximately 008 mgmL Pipette appropriate amount of internal standard solution to obtain
a final concentration of 01 mgmL Dilute to volume with injection solvent Filter approximately 10 mL of
solution with regenerated cellulose 045 microm 25 mm filter into a 20 mL glass vial (Agilent part number 5182-
0567) Make sure there are no air bubbles on bottom of glass vial Cap vial with polypropylene cap (Agilent
part number 5182-9697)
Sample Preparation
Weigh an appropriate amount of sample into a volumetric flask so that the final phenethylamine concentration
is approximately that of the standard solution Pipette appropriate amount of internal standard solution to obtain
a final concentration of 01 mgmL Dilute to volume with injection solvent Sonicate for 15 minutes Filter
approximately 10 mL of solution with regenerated cellulose 045 microm 25 mm filter into a 20 mL glass vial
(Agilent part number 5182-0567) Make sure there are no air bubbles on bottom of glass vial Cap vial with
polypropylene cap (Agilent part number 5182-9697)
Mode HP 3D instrument operated in CE mode
Coated Capillary Mode
Column 50 microm id x 322 cm (237 cm length to detector)
Run Buffer Celixir Reagent B pH 25 (MicroSolv CE)
Detector UV 195 nm
Voltage 10 kV
Temperature 15degC
Injection 50 mbar x 2 s followed by water at 35 mbar
Run Time 6 min
Rinse Time 2 min
Linear Range 002 - 100 mgmL
Repeatability RSD lt16
Correlation Coefficient 10
Accuracy Error less than 32
COMPOUND RRT COMPOUND RRT
doxylamine 0765 ephedrine 0932
chlorpheniramine 0784 phenylephrine 0951
quinine 0804 MDEA 0961
-phenethylamine 0807 ketamine 0962
COMPOUND RRT COMPOUND RRT
chlorquinine 0812 phenyltoxolamine 0971
nicotinamide 0836 n-butylamphetamine 10(46 min)
amphetamine 0868 dextromethorphan 100
methamphetamine 0883 lidocaine 103
procaine 0883 benzocaine 125
MDA 0900 acetaminophen 211
norpseudoephedrine 0906 caffeine 214
MDMA 0914 guaifenesin 214
norephedrine 0917 P2P 224
pseudoephedrine 0919 DMSO (neutral marker) 240
tetracaine 0927 aspirin 271
54 NUCLEAR MAGNETIC RESONANCE
Method MDMA-NMR1
Solvents Deuterium Oxide (D2O) containing DSS or TSP for 0 PPM reference
Internal Standard Stock Solution (ISSS) 5 mgmL Maleic Acid (accurately weighed) in deuterium oxide (D2O)
containing DSS or TSP for 0 ppm reference
Sample Preparation Accurately weigh an amount of sample usually 10-30 mg into a capped test tube and
accurately add a volume normally 10 mL of the ISSS Vortex the sample for several seconds If insolubles
are present add 10 mL D2O (not containing maleic acid or the reference compound) vortex and sonicate 15
minutes Vortex the sample and filter if necessary Place in NMR sample tube
Instrument Varian Mercury 400 MHz with proton detection probe NMR
Spectrometer
Pulse Width 10 micros or 90deg(whichever is less)
Spectral Width (SW) at least containing ndash3 ppm through 13 ppm
Number of Scans multiple of 4 (greater to enhance signal to noise (SN))
Delay between Pulses 45 s
Shimming automatic gradient shimming of Z1-4 shims
Total run timesample 6 min (NT=4) -14 min (NT=16)
Uniformity within spectral width 03 RSD (-06 to 114 PPM)
Run Time 6 min
Linear Range 06 mgmL-60 mgmL
Repeatability lt 4
Correlation Coefficient 10
Accuracy lt 3
Compound MW Solvent Internal
Standard
Solubility
(mgmL)
Signals used for
quantitation
(position in ppm
with number of
protons) Signals in
bold and underlined
are preferred if
other numbers
present
Decompos
ition rate
(hour)
MDMA HCl 22971 D2O maleic
acid gt30
67-69 (m)(3) 60
(s)(2) 35 (sextet)(1)
30dd(1) 28dd(1)
27 (s)(3) 13 (d)(3)
lt01
MDMA
phosphate 29124 D2O
maleic
acid gt19
67-69 (m)(3) 60
(s)(2) 35 (sextet)(1)
30dd(1) 28dd(1)
27 (s)(3) 13 (d)(3)
lt01
6 QUALITATIVE DATA
See spectra on the following pages for FT-IR Vapor Phase IR FT-Raman Mass Spectrometry and Nuclear
Magnetic Resonance
7 REFERENCES
Coates J and Reffner J Visualization of Micro-ATR Infrared Spectroscopy Spectroscopy Vol 14 4
April 1999
Clarke EGC Isolation and Identification of Drugs 2nd Edition The Pharmaceutical Press 1986
Galichat Laurent Y Clarkersquos Analysis of Drugs and Poisons Volume 2 p 1256 Pharmaceutical Press 2004
Budavari S The Merck Index 13th Edition Merck and Co Inc 2001
8 ADDITIONAL RESOURCES
Forendex
Wikipedia
FTIR (KBr) 34-Methylenedioxymethamphetamine Hydrochloride
50 scans 1 nm resolution 5 mg150 mg
FTIR (diamond ATR 3 bounce) 34-Mehtylenedioxymethamphetamine Base
FTIR (1 bounce ATR) MDMA phosphate
32 scans resolution 4 cm-1
IR (Vapor Phase) 34-Methylenedioxymethamphetamine Lot A150B
2 mgmL in CH3OH
FT-RAMAN 34-Methylenedioxymethamphetamine Base
Extracted from MDMA HCl Lot A150B 32 scans 4 cm-1
resolution
FT-RAMAN 34-Methylenedioxymethamphetamine HCl
Lot A150B 32 scans 4 cm-1
resolution
19
48
26
09
34
79
36
61
45
675
34
5
60
41
66
74
71
46
77
21
81
27
88
74
10
39
6
10
97
8
11
54
7
12
47
1
12
89
61
33
69
13
60
5
13
98
01
44
19
15
02
5
16
09
41
62
88
27
93
7
29
32
72
96
79
30
37
23
07
03
33
30
5
00
05
10
15
20
25
30
35
40
45
50
55
60
65
70
75
80In
t
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
19
28
25
19
34
08
37
96
41
00
44
79
47
83
53
40
60
51
63
26
71
61
77
55
81
29
88
63
92
73
10
37
9
10
80
1
11
98
1
12
47
9
13
04
51
33
12
13
69
6
14
01
21
44
32
15
07
2
16
09
51
63
15
27
81
1
28
63
62
90
37
29
33
7
29
69
22
99
14
30
58
4
2
4
6
8
10
12
14
16
18
20
22
24
26
Int
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
FT-RAMAN 34-Methylenedioxymethamphetamine Phosphate Lot 2 TDM-275-01
32 scans 4 cm-1
resolution
Mass Spectrometry (EI) 34-Methylenedioxymethamphetamine
10
66
20
68
25
61
34
42
42
41
47
36
53
98
60
38
63
98
71
41
77
72
81
18
83
67
90
70
10
11
8
10
74
91
10
57
12
01
61
22
83
12
55
1
13
53
1
13
99
3
14
42
0
14
91
7
16
07
81
63
02
23
54
027
98
3
29
40
62
96
43
30
40
83
06
97
00
05
10
15
20
25
30
35
40
45
50
55
Int
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
Mass Spectrometry (CI) 34-Methylenedioxymethamphetamine
1H NMR MDMA base in CDCl3 with TMS 400 MHz
Extracted from MDMA HCl ndash Lot A150B
ppm 673 (d J=783 Hz 1 H) 668 (d J=117 Hz 1 H) 663 (dd J=783 117 Hz 1 H) 592 (s 2 H) 267 -
278 (ddq J=720 630 630 630 630 Hz 1 H) 261 (dd J=1350 724 Hz 1 H) 254 (dd J=1330 626
Hz 1 H) 239 (s 3 H) 104 (d J=626 Hz 3 H)
13C NMR MDMA Base
Extracted from MDMA HCl ndash Lot A 150B
1H NMR MDMA Phosphate in D2O with TSP 400 MHz
Lot 2 TDM-275-01
ppm 688 - 692 (d J=800 Hz 1 H) 686 (d J=137 Hz 1 H) 680 (dd J=800 140 Hz 1 H) 598 (s 2 H)
344 - 355 (ddq J=750 670 670 670 650 Hz 1 H) 299 (dd J=1390 650 Hz 1 H) 285 (dd J=1390
760 Hz 1 H) 270 (s 3 H) 128 (d J=665 Hz 3 H)
13C NMR MDMA Phosphate in D2O with TSP Lot 2 TDM-275-01
1H NMR MDMA Phosphate in CD3OD with TMS Lot 2 TDM-275-01
400 MHz
ppm 679 (d J=098 Hz 1 H) 678 (d J=802 Hz 1 H) 673 (dd J=800 120 Hz 1 H)
593 (s 2 H) 329 - 340 (m 1 H) 308 (dd J=1350 509 Hz 1 H) 269 (s 3 H) 267 (dd
J=1330 960 Hz 1 H) 122 (d J=646 Hz 3 H)
1H NMR MDMA HCl Lot A150B
with maleic acid as internal standard in D2O with TSP 400 MHz
ppm 688 (d J=792 Hz 1 H) 684 (d J=166 Hz 1 H) 676 - 681 (dd J=790 180 Hz 1
H) 597 (s 2 H) 341 - 354 (ddq J=770 670 670 670 650 Hz 1 H) 293 - 302 (dd
J=1400 650 Hz 1 H) 283 (dd J=1400 770 Hz 1 H) 270 (s 3 H) 127 (d J=665 Hz
3 H) Maleic acid 640 (s 2H)
1H NMR MDMA base in CD3OD with TMS
Extracted from MDMA HCl ndash Lot A150B 400 MHz
ppm 669 - 674 (d J=783 Hz 1 H) 667 (d J=137 Hz 1 H) 662 (dd J=780 140 Hz 1
H) 588 (s 2 H) 265 - 276 (m 2 H) 244 (dd J=1530 940 Hz 1 H) 234 (s 3 H) 100
(d J=606 Hz 3 H)
1H NMR MDMA HCl in CD3OD Lot A150B
400 MHz
ppm 680 (d J=160 Hz 1 H) 679 (d J=802 Hz 1 H) 674 (dd J=802 156 Hz 1 H) 593 (s 2 H) 336 -
348 (ddq J=940 650 650 650 530 Hz 1 H) 308 (dd J=1350 528 Hz 1 H) 271 (dd J=1330 940
Hz 1 H) 125 (d J=646 Hz 3 H)
13C NMR MDMA HCl in CD3OD Lot A150B
Optical isomers standards for these compounds were unavailable
No Data Available
COMPOUND
Relative Rf
System
TLC 5
System
TLC 6
34-methenedioxyethylamphetamine 13 18
34-methylenedioxyamphetamine 12 15
34-methylenedioxydimethylamphetamine 11 18
34-methylenedioxymethamphetamine 10 10
34 GAS CHROMATOGRAPHY
Method MDMA-GCS1
Instrument Gas chromatograph operated in split mode with FID
Column 5 phenyl95 methyl silicone 30 m x 025 mm x 025 microm film
thickness
Carrier gas Hydrogen at 20 mLmin
Temperatures Injector 260degC
Detector 270degC
Oven program
1) 90degC initial temperature for 10 min
2) Ramp to 295degC at 30degCmin
3) Hold final temperature for 26 min
Injection Parameters Split Ratio = 501 1 microL injected
Samples are to be dissolved in 41 chloroform methanol and filtered
COMPOUND RRT COMPOUND RRT
amphetamine 058 acetaminophen 118
methamphetamine 064 caffeine 127
safrole 076 methyl stearate 142
C14 085 cocaine 153
34-MDA 095 methyl eicosanoate 154
34-MDMA 100 (439 min) tetraphenylethylene 169
34-MDEA 104 heroin 180
34-MDDMA 106
Method MDMA-GCS2
Instrument Gas Chromatograph operated in split mode with FID
Column 50 phenyl50 methyl silicone 30 m x 025 mm x 025 microm film
thickness
Carrier gas Hydrogen at 20 mLmin
Temperatures Injector 260degC
Detector 270degC
Oven program
1) 90degC initial temperature for 10 min
2) Ramp to 295degC at 30degmin
3) Hold final temperature for 26 min
Injection Parameters Split Ratio = 501 1 microL injected
Samples are to be dissolved in 41 chloroform methanol and filtered
COMPOUND RRT COMPOUND RRT
amphetamine 060 acetaminophen 127
methamphetamine 064 caffeine 134
safrole 078 methyl stearate 126
C14 067 cocaine 153
34-MDA 097 methyl eicosanoate 137
34-MDMA 100 (499 min) tetraphenylethylene 172
34-MDEA 102 heroin 197
34-MDDMA 104
Method MDMA-GCS3
Instrument Gas chromatograph operated in split mode with FID
Column 5 phenyl95 methyl silicone 5 m x 025 mm x 025 microm film
thickness
Carrier gas Hydrogen
1) Initial pressure of 25 psi for 010 min
2) Ramp to 50 psi at 341 psimin
3) Hold final pressure for 077 min
Temperature Injector 260degC
Detector 270degC
Oven program
1) 90degC initial temperature
2) Ramp to 100degC at 10degmin
3) Hold final temperature for 060 min
Injection Parameters Split Ratio = 501 1 microL injected
EZFlash Parameters
1) Time 0 s = 100oC
2) Time 6 s = 110oC
3) Time 50 s = 310oC
4) Time 96 s = 310oC
Samples are to be dissolved in 41 chloroform methanol and filtered
COMPOUND RRT COMPOUND RRT
amphetamine 070 acetaminophen 114
methamphetamine 074 caffeine 122
safrole 082 methyl stearate 123
C14 088 cocaine 144
34-MDA 096 methyl eicosanoate 134
34-MDMA 100 (499 min) tetraphenylethylene 162
34-MDEA 103 heroin 180
34-MDDMA 104
Method MDMA-GCS4
Instrument Gas chromatograph operated in split mode with FID
Column 1 phenyl99 methyl silicone 30 m x 025 mm x 025 microm film
thickness
Carrier gas Hydrogen at 20 mLmin
Temperature Injector 260degC
Detector 270degC
Oven program
1) 90degC initial temperature for 10 min
2) Ramp to 295degC at 30 degreesmin
3) Hold final temperature for 26 min
Injection Parameters Split Ratio = 501 1 microL injected
COMPOUND RRT COMPOUND RRT
amphetamine 053 acetaminophen 119
methamphetamine 165 caffeine 128
safrole 072 methyl stearate 153
C14 091 cocaine 160
34-MDA 094 methyl eicosanoate 167
34-MDMA 100 (436 min) tetraphenylethylene 178
34-MDEA 105 heroin 189
34-MDDMA 108
4 SEPARATION TECHNIQUES
MDMA base hydrochloride or phosphate can be separated from the matrix by solvent extraction using
the solubility data found in Section 22
5 QUANTITATIVE PROCEDURES
51 GAS CHROMATOGRAPHY
Method MDMA-GCQ1
Internal Standard Stock Solution
10 mgmL n-butylamphetamine HCl in chloroform
Standard Solution Preparation
Prepare a standard solution of MDMA HCl at 04 mgmL in chloroform
Sample Preparation
Accurately weigh out 50 mg of sample into a 25 mL volumetric flask and dilute with water to the mark Take a
2 mL aliquot of the solution add 3 mL of IS and 2-3 mL of 05 M KOH Shake Separate layers and extract
twice more with 2-3 mL each time of chloroform Combine fractions dry over sodium sulfate and dilute to
total volume of 10 mL Treat the standard in the same fashion as the sample prior to analysis
Instrument Gas chromatograph operated in split mode with FID
Column DB-1 30 m x 025 mm x 025 microm film thickness
Carrier gas Hydrogen at 13 mLmin
Make-Up gas Nitrogen at 400 mLmin
Temperatures Injector 230degC
Detector 280degC
Oven Program
1) 150degC initial temperature 2 min
2) Ramp to 190degC at 5degmin
3) Hold final temperature for 10 min
Injection Parameters Split Ratio = 201 1 microL injected
Typical Retention Time 34-MDMA 510 min
n-butylamphetamine HCl 392 min
Linear Range 006 mgmL to 20 mgmL
Repeatability RSD less than 20
Correlation Coefficient 09998
Accuracy Error less than 5
COMPOUND RRT COMPOUND RRT COMPOUND RRT
methylbenzylamine 035 methyl paraben 077 caffeine 186
P-2-P 038 salicylamide 077 antipyrine 200
amphetamine 039 penicillin 078 benzphetamine 204
nicotinic acid 042 phenmetrazine 081 diphenhydramine 214
phentermine 042 MDP-2-P 084 aminopyrine 226
methamphetamine 044 phendimetrazine 086 doxylamine 231
fenfluramine 048 MDA 087 palmitic acid 245
ethylamphetamine 049 MDMA 100 (51 min) phthalic acid 245
dimethylamphetamine 050 aminorex 105 dipyrone 251
safrole 055 methyl aminorex 105 procaine 266
salicylic acid 056 MDEA 113 eicosane 267
cathine 059 ibuprofen 124 dextromethorphan 312
phenylpropanolamine 059 MBDB 126 strychnine 317
methcathinone 060 hexadecane 128 phenyl-2-naphthalene 327
nicotinamide 062 glycerol glycolate 130 amitriptyline 334
chlorpheniramine 065 acetaminophen 135 scopolamine 371
chloroephedrine 066 MMDA 138 tetracosane 407
pseudoephedrine 066 phenacetin 141 chlordiazepoxide 431
ephedrine 068 chloro-MDMA 149 quinine 523
butylamphetamine 077 methylphenidate 163
52 HIGH PERFORMANCE LIQUID CHROMATOGRAPHY
Method MDMA-LCQ1
Standard Solution Preparation
Prepare a standard solution of MDMA at approximately 05 mgmL using water buffer or methanol
Sample Preparation
Accurately weigh an amount of sample into an appropriate volumetric or Erlenmeyer flask and dilute so
that the final MDMA concentration is approximately that of the standard solution
Instrument High performance liquid chromatograph equipped with diode array
Column 5 microm Phenomenex Luna 150 mm x 32 mm at 35C
Detector UV 210 nm
Flow 10 mLmin
Injection Volume 5 microL
Buffer 4000 mL distilled water 225 mL phosphoric acid adjust to pH 22-
23 with triethanolamine (approx 22 mL)
Mobile Phase Bufferacetonitrile 9010
Typical Retention Time 34-MDMA 1054 min
Linear Range 005 mgmL ndash 2 mgmL
Repeatability RSD less than 05
Correlation Coefficient 09999
Accuracy Error less than 5
COMPOUND RRT COMPOUND RRT
phenylpropanolamine 060 methyl aminorex 101
methyl benzylamine 062 phentermine 102
cathine 063 chloroephedrine 103
doxylamine 069 ethylamphetamine 105
dipyrone 070 MDP-2-P 105
ephedrine 072 lidocaine 107
methcathinone 073 caffeine q
pseudoephedrine 073 MDEA 113
amphetamine 084 phenyl-2-naphthalene 113
theophylline 087 phthalic acid 113
methapyrilene 089 strychnine 114
phenmetrazine 089 MMDA 117
methamphetamine 091 MBDB 125
phendimetrazine 091 salicylamide 127
COMPOUND RRT COMPOUND RRT
scopolamine 092 acetaminophen 129
MDA 093 chloro-MDMA 137
quinine 096 methylphenidate 138
saccharin 096 glycerol glycolate 148
dimethylamphetamine 097 chlorpheniramine 155
MDMA 100 (1054 min) aspirin 181
chlordiazepoxide 187
53 CAPILLARY ELECTROPHORESIS
Method MDMA-CEQ1
Internal Standard Stock Solution
050 mgmL n-butylamphetamine in 50 mM sodium phosphate at pH 70
Standard Solution Preparation
Accurately weigh and prepare a standard solution of 34-methylenedioxymethamphetamine hydrochloride at
approximately 08 mgmL using the internal standard stock solution
Sample Preparation
Accurately weigh an amount of sample into a volumetric flask and dilute with internal standard stock solution
If necessary dilute the sample so the final concentration approximates the standard concentration or falls within
the linear range Filter sample with 045-micron filter
Mode Cyclodextrin system analysis
Column 49 cm x 52 microm fused silica capillary
Run Buffer 10 mM gamma-highly sulfated cyclodextrin in 50 mM sodium phosphate
at pH 70
Detector UV 210 nm
Voltage 12 kV
Temperature 30degC air cooled
Injection 1 sec hydrodynamic at 50 mbars
Run Time 17 min
Rinse Time 20 min
Linear Range 002 - 100 mgmL
Repeatability RSD of area less than 15
Correlation Coefficient 0999
Accuracy Error less than 5
COMPOUND RRT COMPOUND RRT
d-methamphetamine 066 l-pseudoephedrine 098
d-ephedrine 074 MDMA 100 (1104 min)
MDA 080 l-ephedrine 109
cathine 085 MDEA 112
l-methamphetamine 089 MDMA 119
d-amphetamine 094 l-norephedrine 132
d-norephedrine 094 l-amphetamine 134
d-pseudoephedrine 097 MDA 136
MDEA 149
Method MDMA-CEQ2
Internal Standard Stock Solution
10 mgmL n-butylamphetamine in 38 mM phosphate buffer (pH 25)
Standard Solution Preparation
Weigh an appropriate amount of standard 34-MDMA HCl into a volumetric flask to obtain a final
concentration of approximately 008 mgmL Pipette appropriate amount of internal standard solution to obtain
a final concentration of 01 mgmL Dilute to volume with injection solvent Filter approximately 10 mL of
solution with regenerated cellulose 045 microm 25 mm filter into a 20 mL glass vial (Agilent part number 5182-
0567) Make sure there are no air bubbles on bottom of glass vial Cap vial with polypropylene cap (Agilent
part number 5182-9697)
Sample Preparation
Weigh an appropriate amount of sample into a volumetric flask so that the final phenethylamine concentration
is approximately that of the standard solution Pipette appropriate amount of internal standard solution to obtain
a final concentration of 01 mgmL Dilute to volume with injection solvent Sonicate for 15 minutes Filter
approximately 10 mL of solution with regenerated cellulose 045 microm 25 mm filter into a 20 mL glass vial
(Agilent part number 5182-0567) Make sure there are no air bubbles on bottom of glass vial Cap vial with
polypropylene cap (Agilent part number 5182-9697)
Mode HP 3D instrument operated in CE mode
Coated Capillary Mode
Column 50 microm id x 322 cm (237 cm length to detector)
Run Buffer Celixir Reagent B pH 25 (MicroSolv CE)
Detector UV 195 nm
Voltage 10 kV
Temperature 15degC
Injection 50 mbar x 2 s followed by water at 35 mbar
Run Time 6 min
Rinse Time 2 min
Linear Range 002 - 100 mgmL
Repeatability RSD lt16
Correlation Coefficient 10
Accuracy Error less than 32
COMPOUND RRT COMPOUND RRT
doxylamine 0765 ephedrine 0932
chlorpheniramine 0784 phenylephrine 0951
quinine 0804 MDEA 0961
-phenethylamine 0807 ketamine 0962
COMPOUND RRT COMPOUND RRT
chlorquinine 0812 phenyltoxolamine 0971
nicotinamide 0836 n-butylamphetamine 10(46 min)
amphetamine 0868 dextromethorphan 100
methamphetamine 0883 lidocaine 103
procaine 0883 benzocaine 125
MDA 0900 acetaminophen 211
norpseudoephedrine 0906 caffeine 214
MDMA 0914 guaifenesin 214
norephedrine 0917 P2P 224
pseudoephedrine 0919 DMSO (neutral marker) 240
tetracaine 0927 aspirin 271
54 NUCLEAR MAGNETIC RESONANCE
Method MDMA-NMR1
Solvents Deuterium Oxide (D2O) containing DSS or TSP for 0 PPM reference
Internal Standard Stock Solution (ISSS) 5 mgmL Maleic Acid (accurately weighed) in deuterium oxide (D2O)
containing DSS or TSP for 0 ppm reference
Sample Preparation Accurately weigh an amount of sample usually 10-30 mg into a capped test tube and
accurately add a volume normally 10 mL of the ISSS Vortex the sample for several seconds If insolubles
are present add 10 mL D2O (not containing maleic acid or the reference compound) vortex and sonicate 15
minutes Vortex the sample and filter if necessary Place in NMR sample tube
Instrument Varian Mercury 400 MHz with proton detection probe NMR
Spectrometer
Pulse Width 10 micros or 90deg(whichever is less)
Spectral Width (SW) at least containing ndash3 ppm through 13 ppm
Number of Scans multiple of 4 (greater to enhance signal to noise (SN))
Delay between Pulses 45 s
Shimming automatic gradient shimming of Z1-4 shims
Total run timesample 6 min (NT=4) -14 min (NT=16)
Uniformity within spectral width 03 RSD (-06 to 114 PPM)
Run Time 6 min
Linear Range 06 mgmL-60 mgmL
Repeatability lt 4
Correlation Coefficient 10
Accuracy lt 3
Compound MW Solvent Internal
Standard
Solubility
(mgmL)
Signals used for
quantitation
(position in ppm
with number of
protons) Signals in
bold and underlined
are preferred if
other numbers
present
Decompos
ition rate
(hour)
MDMA HCl 22971 D2O maleic
acid gt30
67-69 (m)(3) 60
(s)(2) 35 (sextet)(1)
30dd(1) 28dd(1)
27 (s)(3) 13 (d)(3)
lt01
MDMA
phosphate 29124 D2O
maleic
acid gt19
67-69 (m)(3) 60
(s)(2) 35 (sextet)(1)
30dd(1) 28dd(1)
27 (s)(3) 13 (d)(3)
lt01
6 QUALITATIVE DATA
See spectra on the following pages for FT-IR Vapor Phase IR FT-Raman Mass Spectrometry and Nuclear
Magnetic Resonance
7 REFERENCES
Coates J and Reffner J Visualization of Micro-ATR Infrared Spectroscopy Spectroscopy Vol 14 4
April 1999
Clarke EGC Isolation and Identification of Drugs 2nd Edition The Pharmaceutical Press 1986
Galichat Laurent Y Clarkersquos Analysis of Drugs and Poisons Volume 2 p 1256 Pharmaceutical Press 2004
Budavari S The Merck Index 13th Edition Merck and Co Inc 2001
8 ADDITIONAL RESOURCES
Forendex
Wikipedia
FTIR (KBr) 34-Methylenedioxymethamphetamine Hydrochloride
50 scans 1 nm resolution 5 mg150 mg
FTIR (diamond ATR 3 bounce) 34-Mehtylenedioxymethamphetamine Base
FTIR (1 bounce ATR) MDMA phosphate
32 scans resolution 4 cm-1
IR (Vapor Phase) 34-Methylenedioxymethamphetamine Lot A150B
2 mgmL in CH3OH
FT-RAMAN 34-Methylenedioxymethamphetamine Base
Extracted from MDMA HCl Lot A150B 32 scans 4 cm-1
resolution
FT-RAMAN 34-Methylenedioxymethamphetamine HCl
Lot A150B 32 scans 4 cm-1
resolution
19
48
26
09
34
79
36
61
45
675
34
5
60
41
66
74
71
46
77
21
81
27
88
74
10
39
6
10
97
8
11
54
7
12
47
1
12
89
61
33
69
13
60
5
13
98
01
44
19
15
02
5
16
09
41
62
88
27
93
7
29
32
72
96
79
30
37
23
07
03
33
30
5
00
05
10
15
20
25
30
35
40
45
50
55
60
65
70
75
80In
t
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
19
28
25
19
34
08
37
96
41
00
44
79
47
83
53
40
60
51
63
26
71
61
77
55
81
29
88
63
92
73
10
37
9
10
80
1
11
98
1
12
47
9
13
04
51
33
12
13
69
6
14
01
21
44
32
15
07
2
16
09
51
63
15
27
81
1
28
63
62
90
37
29
33
7
29
69
22
99
14
30
58
4
2
4
6
8
10
12
14
16
18
20
22
24
26
Int
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
FT-RAMAN 34-Methylenedioxymethamphetamine Phosphate Lot 2 TDM-275-01
32 scans 4 cm-1
resolution
Mass Spectrometry (EI) 34-Methylenedioxymethamphetamine
10
66
20
68
25
61
34
42
42
41
47
36
53
98
60
38
63
98
71
41
77
72
81
18
83
67
90
70
10
11
8
10
74
91
10
57
12
01
61
22
83
12
55
1
13
53
1
13
99
3
14
42
0
14
91
7
16
07
81
63
02
23
54
027
98
3
29
40
62
96
43
30
40
83
06
97
00
05
10
15
20
25
30
35
40
45
50
55
Int
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
Mass Spectrometry (CI) 34-Methylenedioxymethamphetamine
1H NMR MDMA base in CDCl3 with TMS 400 MHz
Extracted from MDMA HCl ndash Lot A150B
ppm 673 (d J=783 Hz 1 H) 668 (d J=117 Hz 1 H) 663 (dd J=783 117 Hz 1 H) 592 (s 2 H) 267 -
278 (ddq J=720 630 630 630 630 Hz 1 H) 261 (dd J=1350 724 Hz 1 H) 254 (dd J=1330 626
Hz 1 H) 239 (s 3 H) 104 (d J=626 Hz 3 H)
13C NMR MDMA Base
Extracted from MDMA HCl ndash Lot A 150B
1H NMR MDMA Phosphate in D2O with TSP 400 MHz
Lot 2 TDM-275-01
ppm 688 - 692 (d J=800 Hz 1 H) 686 (d J=137 Hz 1 H) 680 (dd J=800 140 Hz 1 H) 598 (s 2 H)
344 - 355 (ddq J=750 670 670 670 650 Hz 1 H) 299 (dd J=1390 650 Hz 1 H) 285 (dd J=1390
760 Hz 1 H) 270 (s 3 H) 128 (d J=665 Hz 3 H)
13C NMR MDMA Phosphate in D2O with TSP Lot 2 TDM-275-01
1H NMR MDMA Phosphate in CD3OD with TMS Lot 2 TDM-275-01
400 MHz
ppm 679 (d J=098 Hz 1 H) 678 (d J=802 Hz 1 H) 673 (dd J=800 120 Hz 1 H)
593 (s 2 H) 329 - 340 (m 1 H) 308 (dd J=1350 509 Hz 1 H) 269 (s 3 H) 267 (dd
J=1330 960 Hz 1 H) 122 (d J=646 Hz 3 H)
1H NMR MDMA HCl Lot A150B
with maleic acid as internal standard in D2O with TSP 400 MHz
ppm 688 (d J=792 Hz 1 H) 684 (d J=166 Hz 1 H) 676 - 681 (dd J=790 180 Hz 1
H) 597 (s 2 H) 341 - 354 (ddq J=770 670 670 670 650 Hz 1 H) 293 - 302 (dd
J=1400 650 Hz 1 H) 283 (dd J=1400 770 Hz 1 H) 270 (s 3 H) 127 (d J=665 Hz
3 H) Maleic acid 640 (s 2H)
1H NMR MDMA base in CD3OD with TMS
Extracted from MDMA HCl ndash Lot A150B 400 MHz
ppm 669 - 674 (d J=783 Hz 1 H) 667 (d J=137 Hz 1 H) 662 (dd J=780 140 Hz 1
H) 588 (s 2 H) 265 - 276 (m 2 H) 244 (dd J=1530 940 Hz 1 H) 234 (s 3 H) 100
(d J=606 Hz 3 H)
1H NMR MDMA HCl in CD3OD Lot A150B
400 MHz
ppm 680 (d J=160 Hz 1 H) 679 (d J=802 Hz 1 H) 674 (dd J=802 156 Hz 1 H) 593 (s 2 H) 336 -
348 (ddq J=940 650 650 650 530 Hz 1 H) 308 (dd J=1350 528 Hz 1 H) 271 (dd J=1330 940
Hz 1 H) 125 (d J=646 Hz 3 H)
13C NMR MDMA HCl in CD3OD Lot A150B
Optical isomers standards for these compounds were unavailable
No Data Available
34-MDMA 100 (439 min) tetraphenylethylene 169
34-MDEA 104 heroin 180
34-MDDMA 106
Method MDMA-GCS2
Instrument Gas Chromatograph operated in split mode with FID
Column 50 phenyl50 methyl silicone 30 m x 025 mm x 025 microm film
thickness
Carrier gas Hydrogen at 20 mLmin
Temperatures Injector 260degC
Detector 270degC
Oven program
1) 90degC initial temperature for 10 min
2) Ramp to 295degC at 30degmin
3) Hold final temperature for 26 min
Injection Parameters Split Ratio = 501 1 microL injected
Samples are to be dissolved in 41 chloroform methanol and filtered
COMPOUND RRT COMPOUND RRT
amphetamine 060 acetaminophen 127
methamphetamine 064 caffeine 134
safrole 078 methyl stearate 126
C14 067 cocaine 153
34-MDA 097 methyl eicosanoate 137
34-MDMA 100 (499 min) tetraphenylethylene 172
34-MDEA 102 heroin 197
34-MDDMA 104
Method MDMA-GCS3
Instrument Gas chromatograph operated in split mode with FID
Column 5 phenyl95 methyl silicone 5 m x 025 mm x 025 microm film
thickness
Carrier gas Hydrogen
1) Initial pressure of 25 psi for 010 min
2) Ramp to 50 psi at 341 psimin
3) Hold final pressure for 077 min
Temperature Injector 260degC
Detector 270degC
Oven program
1) 90degC initial temperature
2) Ramp to 100degC at 10degmin
3) Hold final temperature for 060 min
Injection Parameters Split Ratio = 501 1 microL injected
EZFlash Parameters
1) Time 0 s = 100oC
2) Time 6 s = 110oC
3) Time 50 s = 310oC
4) Time 96 s = 310oC
Samples are to be dissolved in 41 chloroform methanol and filtered
COMPOUND RRT COMPOUND RRT
amphetamine 070 acetaminophen 114
methamphetamine 074 caffeine 122
safrole 082 methyl stearate 123
C14 088 cocaine 144
34-MDA 096 methyl eicosanoate 134
34-MDMA 100 (499 min) tetraphenylethylene 162
34-MDEA 103 heroin 180
34-MDDMA 104
Method MDMA-GCS4
Instrument Gas chromatograph operated in split mode with FID
Column 1 phenyl99 methyl silicone 30 m x 025 mm x 025 microm film
thickness
Carrier gas Hydrogen at 20 mLmin
Temperature Injector 260degC
Detector 270degC
Oven program
1) 90degC initial temperature for 10 min
2) Ramp to 295degC at 30 degreesmin
3) Hold final temperature for 26 min
Injection Parameters Split Ratio = 501 1 microL injected
COMPOUND RRT COMPOUND RRT
amphetamine 053 acetaminophen 119
methamphetamine 165 caffeine 128
safrole 072 methyl stearate 153
C14 091 cocaine 160
34-MDA 094 methyl eicosanoate 167
34-MDMA 100 (436 min) tetraphenylethylene 178
34-MDEA 105 heroin 189
34-MDDMA 108
4 SEPARATION TECHNIQUES
MDMA base hydrochloride or phosphate can be separated from the matrix by solvent extraction using
the solubility data found in Section 22
5 QUANTITATIVE PROCEDURES
51 GAS CHROMATOGRAPHY
Method MDMA-GCQ1
Internal Standard Stock Solution
10 mgmL n-butylamphetamine HCl in chloroform
Standard Solution Preparation
Prepare a standard solution of MDMA HCl at 04 mgmL in chloroform
Sample Preparation
Accurately weigh out 50 mg of sample into a 25 mL volumetric flask and dilute with water to the mark Take a
2 mL aliquot of the solution add 3 mL of IS and 2-3 mL of 05 M KOH Shake Separate layers and extract
twice more with 2-3 mL each time of chloroform Combine fractions dry over sodium sulfate and dilute to
total volume of 10 mL Treat the standard in the same fashion as the sample prior to analysis
Instrument Gas chromatograph operated in split mode with FID
Column DB-1 30 m x 025 mm x 025 microm film thickness
Carrier gas Hydrogen at 13 mLmin
Make-Up gas Nitrogen at 400 mLmin
Temperatures Injector 230degC
Detector 280degC
Oven Program
1) 150degC initial temperature 2 min
2) Ramp to 190degC at 5degmin
3) Hold final temperature for 10 min
Injection Parameters Split Ratio = 201 1 microL injected
Typical Retention Time 34-MDMA 510 min
n-butylamphetamine HCl 392 min
Linear Range 006 mgmL to 20 mgmL
Repeatability RSD less than 20
Correlation Coefficient 09998
Accuracy Error less than 5
COMPOUND RRT COMPOUND RRT COMPOUND RRT
methylbenzylamine 035 methyl paraben 077 caffeine 186
P-2-P 038 salicylamide 077 antipyrine 200
amphetamine 039 penicillin 078 benzphetamine 204
nicotinic acid 042 phenmetrazine 081 diphenhydramine 214
phentermine 042 MDP-2-P 084 aminopyrine 226
methamphetamine 044 phendimetrazine 086 doxylamine 231
fenfluramine 048 MDA 087 palmitic acid 245
ethylamphetamine 049 MDMA 100 (51 min) phthalic acid 245
dimethylamphetamine 050 aminorex 105 dipyrone 251
safrole 055 methyl aminorex 105 procaine 266
salicylic acid 056 MDEA 113 eicosane 267
cathine 059 ibuprofen 124 dextromethorphan 312
phenylpropanolamine 059 MBDB 126 strychnine 317
methcathinone 060 hexadecane 128 phenyl-2-naphthalene 327
nicotinamide 062 glycerol glycolate 130 amitriptyline 334
chlorpheniramine 065 acetaminophen 135 scopolamine 371
chloroephedrine 066 MMDA 138 tetracosane 407
pseudoephedrine 066 phenacetin 141 chlordiazepoxide 431
ephedrine 068 chloro-MDMA 149 quinine 523
butylamphetamine 077 methylphenidate 163
52 HIGH PERFORMANCE LIQUID CHROMATOGRAPHY
Method MDMA-LCQ1
Standard Solution Preparation
Prepare a standard solution of MDMA at approximately 05 mgmL using water buffer or methanol
Sample Preparation
Accurately weigh an amount of sample into an appropriate volumetric or Erlenmeyer flask and dilute so
that the final MDMA concentration is approximately that of the standard solution
Instrument High performance liquid chromatograph equipped with diode array
Column 5 microm Phenomenex Luna 150 mm x 32 mm at 35C
Detector UV 210 nm
Flow 10 mLmin
Injection Volume 5 microL
Buffer 4000 mL distilled water 225 mL phosphoric acid adjust to pH 22-
23 with triethanolamine (approx 22 mL)
Mobile Phase Bufferacetonitrile 9010
Typical Retention Time 34-MDMA 1054 min
Linear Range 005 mgmL ndash 2 mgmL
Repeatability RSD less than 05
Correlation Coefficient 09999
Accuracy Error less than 5
COMPOUND RRT COMPOUND RRT
phenylpropanolamine 060 methyl aminorex 101
methyl benzylamine 062 phentermine 102
cathine 063 chloroephedrine 103
doxylamine 069 ethylamphetamine 105
dipyrone 070 MDP-2-P 105
ephedrine 072 lidocaine 107
methcathinone 073 caffeine q
pseudoephedrine 073 MDEA 113
amphetamine 084 phenyl-2-naphthalene 113
theophylline 087 phthalic acid 113
methapyrilene 089 strychnine 114
phenmetrazine 089 MMDA 117
methamphetamine 091 MBDB 125
phendimetrazine 091 salicylamide 127
COMPOUND RRT COMPOUND RRT
scopolamine 092 acetaminophen 129
MDA 093 chloro-MDMA 137
quinine 096 methylphenidate 138
saccharin 096 glycerol glycolate 148
dimethylamphetamine 097 chlorpheniramine 155
MDMA 100 (1054 min) aspirin 181
chlordiazepoxide 187
53 CAPILLARY ELECTROPHORESIS
Method MDMA-CEQ1
Internal Standard Stock Solution
050 mgmL n-butylamphetamine in 50 mM sodium phosphate at pH 70
Standard Solution Preparation
Accurately weigh and prepare a standard solution of 34-methylenedioxymethamphetamine hydrochloride at
approximately 08 mgmL using the internal standard stock solution
Sample Preparation
Accurately weigh an amount of sample into a volumetric flask and dilute with internal standard stock solution
If necessary dilute the sample so the final concentration approximates the standard concentration or falls within
the linear range Filter sample with 045-micron filter
Mode Cyclodextrin system analysis
Column 49 cm x 52 microm fused silica capillary
Run Buffer 10 mM gamma-highly sulfated cyclodextrin in 50 mM sodium phosphate
at pH 70
Detector UV 210 nm
Voltage 12 kV
Temperature 30degC air cooled
Injection 1 sec hydrodynamic at 50 mbars
Run Time 17 min
Rinse Time 20 min
Linear Range 002 - 100 mgmL
Repeatability RSD of area less than 15
Correlation Coefficient 0999
Accuracy Error less than 5
COMPOUND RRT COMPOUND RRT
d-methamphetamine 066 l-pseudoephedrine 098
d-ephedrine 074 MDMA 100 (1104 min)
MDA 080 l-ephedrine 109
cathine 085 MDEA 112
l-methamphetamine 089 MDMA 119
d-amphetamine 094 l-norephedrine 132
d-norephedrine 094 l-amphetamine 134
d-pseudoephedrine 097 MDA 136
MDEA 149
Method MDMA-CEQ2
Internal Standard Stock Solution
10 mgmL n-butylamphetamine in 38 mM phosphate buffer (pH 25)
Standard Solution Preparation
Weigh an appropriate amount of standard 34-MDMA HCl into a volumetric flask to obtain a final
concentration of approximately 008 mgmL Pipette appropriate amount of internal standard solution to obtain
a final concentration of 01 mgmL Dilute to volume with injection solvent Filter approximately 10 mL of
solution with regenerated cellulose 045 microm 25 mm filter into a 20 mL glass vial (Agilent part number 5182-
0567) Make sure there are no air bubbles on bottom of glass vial Cap vial with polypropylene cap (Agilent
part number 5182-9697)
Sample Preparation
Weigh an appropriate amount of sample into a volumetric flask so that the final phenethylamine concentration
is approximately that of the standard solution Pipette appropriate amount of internal standard solution to obtain
a final concentration of 01 mgmL Dilute to volume with injection solvent Sonicate for 15 minutes Filter
approximately 10 mL of solution with regenerated cellulose 045 microm 25 mm filter into a 20 mL glass vial
(Agilent part number 5182-0567) Make sure there are no air bubbles on bottom of glass vial Cap vial with
polypropylene cap (Agilent part number 5182-9697)
Mode HP 3D instrument operated in CE mode
Coated Capillary Mode
Column 50 microm id x 322 cm (237 cm length to detector)
Run Buffer Celixir Reagent B pH 25 (MicroSolv CE)
Detector UV 195 nm
Voltage 10 kV
Temperature 15degC
Injection 50 mbar x 2 s followed by water at 35 mbar
Run Time 6 min
Rinse Time 2 min
Linear Range 002 - 100 mgmL
Repeatability RSD lt16
Correlation Coefficient 10
Accuracy Error less than 32
COMPOUND RRT COMPOUND RRT
doxylamine 0765 ephedrine 0932
chlorpheniramine 0784 phenylephrine 0951
quinine 0804 MDEA 0961
-phenethylamine 0807 ketamine 0962
COMPOUND RRT COMPOUND RRT
chlorquinine 0812 phenyltoxolamine 0971
nicotinamide 0836 n-butylamphetamine 10(46 min)
amphetamine 0868 dextromethorphan 100
methamphetamine 0883 lidocaine 103
procaine 0883 benzocaine 125
MDA 0900 acetaminophen 211
norpseudoephedrine 0906 caffeine 214
MDMA 0914 guaifenesin 214
norephedrine 0917 P2P 224
pseudoephedrine 0919 DMSO (neutral marker) 240
tetracaine 0927 aspirin 271
54 NUCLEAR MAGNETIC RESONANCE
Method MDMA-NMR1
Solvents Deuterium Oxide (D2O) containing DSS or TSP for 0 PPM reference
Internal Standard Stock Solution (ISSS) 5 mgmL Maleic Acid (accurately weighed) in deuterium oxide (D2O)
containing DSS or TSP for 0 ppm reference
Sample Preparation Accurately weigh an amount of sample usually 10-30 mg into a capped test tube and
accurately add a volume normally 10 mL of the ISSS Vortex the sample for several seconds If insolubles
are present add 10 mL D2O (not containing maleic acid or the reference compound) vortex and sonicate 15
minutes Vortex the sample and filter if necessary Place in NMR sample tube
Instrument Varian Mercury 400 MHz with proton detection probe NMR
Spectrometer
Pulse Width 10 micros or 90deg(whichever is less)
Spectral Width (SW) at least containing ndash3 ppm through 13 ppm
Number of Scans multiple of 4 (greater to enhance signal to noise (SN))
Delay between Pulses 45 s
Shimming automatic gradient shimming of Z1-4 shims
Total run timesample 6 min (NT=4) -14 min (NT=16)
Uniformity within spectral width 03 RSD (-06 to 114 PPM)
Run Time 6 min
Linear Range 06 mgmL-60 mgmL
Repeatability lt 4
Correlation Coefficient 10
Accuracy lt 3
Compound MW Solvent Internal
Standard
Solubility
(mgmL)
Signals used for
quantitation
(position in ppm
with number of
protons) Signals in
bold and underlined
are preferred if
other numbers
present
Decompos
ition rate
(hour)
MDMA HCl 22971 D2O maleic
acid gt30
67-69 (m)(3) 60
(s)(2) 35 (sextet)(1)
30dd(1) 28dd(1)
27 (s)(3) 13 (d)(3)
lt01
MDMA
phosphate 29124 D2O
maleic
acid gt19
67-69 (m)(3) 60
(s)(2) 35 (sextet)(1)
30dd(1) 28dd(1)
27 (s)(3) 13 (d)(3)
lt01
6 QUALITATIVE DATA
See spectra on the following pages for FT-IR Vapor Phase IR FT-Raman Mass Spectrometry and Nuclear
Magnetic Resonance
7 REFERENCES
Coates J and Reffner J Visualization of Micro-ATR Infrared Spectroscopy Spectroscopy Vol 14 4
April 1999
Clarke EGC Isolation and Identification of Drugs 2nd Edition The Pharmaceutical Press 1986
Galichat Laurent Y Clarkersquos Analysis of Drugs and Poisons Volume 2 p 1256 Pharmaceutical Press 2004
Budavari S The Merck Index 13th Edition Merck and Co Inc 2001
8 ADDITIONAL RESOURCES
Forendex
Wikipedia
FTIR (KBr) 34-Methylenedioxymethamphetamine Hydrochloride
50 scans 1 nm resolution 5 mg150 mg
FTIR (diamond ATR 3 bounce) 34-Mehtylenedioxymethamphetamine Base
FTIR (1 bounce ATR) MDMA phosphate
32 scans resolution 4 cm-1
IR (Vapor Phase) 34-Methylenedioxymethamphetamine Lot A150B
2 mgmL in CH3OH
FT-RAMAN 34-Methylenedioxymethamphetamine Base
Extracted from MDMA HCl Lot A150B 32 scans 4 cm-1
resolution
FT-RAMAN 34-Methylenedioxymethamphetamine HCl
Lot A150B 32 scans 4 cm-1
resolution
19
48
26
09
34
79
36
61
45
675
34
5
60
41
66
74
71
46
77
21
81
27
88
74
10
39
6
10
97
8
11
54
7
12
47
1
12
89
61
33
69
13
60
5
13
98
01
44
19
15
02
5
16
09
41
62
88
27
93
7
29
32
72
96
79
30
37
23
07
03
33
30
5
00
05
10
15
20
25
30
35
40
45
50
55
60
65
70
75
80In
t
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
19
28
25
19
34
08
37
96
41
00
44
79
47
83
53
40
60
51
63
26
71
61
77
55
81
29
88
63
92
73
10
37
9
10
80
1
11
98
1
12
47
9
13
04
51
33
12
13
69
6
14
01
21
44
32
15
07
2
16
09
51
63
15
27
81
1
28
63
62
90
37
29
33
7
29
69
22
99
14
30
58
4
2
4
6
8
10
12
14
16
18
20
22
24
26
Int
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
FT-RAMAN 34-Methylenedioxymethamphetamine Phosphate Lot 2 TDM-275-01
32 scans 4 cm-1
resolution
Mass Spectrometry (EI) 34-Methylenedioxymethamphetamine
10
66
20
68
25
61
34
42
42
41
47
36
53
98
60
38
63
98
71
41
77
72
81
18
83
67
90
70
10
11
8
10
74
91
10
57
12
01
61
22
83
12
55
1
13
53
1
13
99
3
14
42
0
14
91
7
16
07
81
63
02
23
54
027
98
3
29
40
62
96
43
30
40
83
06
97
00
05
10
15
20
25
30
35
40
45
50
55
Int
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
Mass Spectrometry (CI) 34-Methylenedioxymethamphetamine
1H NMR MDMA base in CDCl3 with TMS 400 MHz
Extracted from MDMA HCl ndash Lot A150B
ppm 673 (d J=783 Hz 1 H) 668 (d J=117 Hz 1 H) 663 (dd J=783 117 Hz 1 H) 592 (s 2 H) 267 -
278 (ddq J=720 630 630 630 630 Hz 1 H) 261 (dd J=1350 724 Hz 1 H) 254 (dd J=1330 626
Hz 1 H) 239 (s 3 H) 104 (d J=626 Hz 3 H)
13C NMR MDMA Base
Extracted from MDMA HCl ndash Lot A 150B
1H NMR MDMA Phosphate in D2O with TSP 400 MHz
Lot 2 TDM-275-01
ppm 688 - 692 (d J=800 Hz 1 H) 686 (d J=137 Hz 1 H) 680 (dd J=800 140 Hz 1 H) 598 (s 2 H)
344 - 355 (ddq J=750 670 670 670 650 Hz 1 H) 299 (dd J=1390 650 Hz 1 H) 285 (dd J=1390
760 Hz 1 H) 270 (s 3 H) 128 (d J=665 Hz 3 H)
13C NMR MDMA Phosphate in D2O with TSP Lot 2 TDM-275-01
1H NMR MDMA Phosphate in CD3OD with TMS Lot 2 TDM-275-01
400 MHz
ppm 679 (d J=098 Hz 1 H) 678 (d J=802 Hz 1 H) 673 (dd J=800 120 Hz 1 H)
593 (s 2 H) 329 - 340 (m 1 H) 308 (dd J=1350 509 Hz 1 H) 269 (s 3 H) 267 (dd
J=1330 960 Hz 1 H) 122 (d J=646 Hz 3 H)
1H NMR MDMA HCl Lot A150B
with maleic acid as internal standard in D2O with TSP 400 MHz
ppm 688 (d J=792 Hz 1 H) 684 (d J=166 Hz 1 H) 676 - 681 (dd J=790 180 Hz 1
H) 597 (s 2 H) 341 - 354 (ddq J=770 670 670 670 650 Hz 1 H) 293 - 302 (dd
J=1400 650 Hz 1 H) 283 (dd J=1400 770 Hz 1 H) 270 (s 3 H) 127 (d J=665 Hz
3 H) Maleic acid 640 (s 2H)
1H NMR MDMA base in CD3OD with TMS
Extracted from MDMA HCl ndash Lot A150B 400 MHz
ppm 669 - 674 (d J=783 Hz 1 H) 667 (d J=137 Hz 1 H) 662 (dd J=780 140 Hz 1
H) 588 (s 2 H) 265 - 276 (m 2 H) 244 (dd J=1530 940 Hz 1 H) 234 (s 3 H) 100
(d J=606 Hz 3 H)
1H NMR MDMA HCl in CD3OD Lot A150B
400 MHz
ppm 680 (d J=160 Hz 1 H) 679 (d J=802 Hz 1 H) 674 (dd J=802 156 Hz 1 H) 593 (s 2 H) 336 -
348 (ddq J=940 650 650 650 530 Hz 1 H) 308 (dd J=1350 528 Hz 1 H) 271 (dd J=1330 940
Hz 1 H) 125 (d J=646 Hz 3 H)
13C NMR MDMA HCl in CD3OD Lot A150B
Optical isomers standards for these compounds were unavailable
No Data Available
Instrument Gas chromatograph operated in split mode with FID
Column 5 phenyl95 methyl silicone 5 m x 025 mm x 025 microm film
thickness
Carrier gas Hydrogen
1) Initial pressure of 25 psi for 010 min
2) Ramp to 50 psi at 341 psimin
3) Hold final pressure for 077 min
Temperature Injector 260degC
Detector 270degC
Oven program
1) 90degC initial temperature
2) Ramp to 100degC at 10degmin
3) Hold final temperature for 060 min
Injection Parameters Split Ratio = 501 1 microL injected
EZFlash Parameters
1) Time 0 s = 100oC
2) Time 6 s = 110oC
3) Time 50 s = 310oC
4) Time 96 s = 310oC
Samples are to be dissolved in 41 chloroform methanol and filtered
COMPOUND RRT COMPOUND RRT
amphetamine 070 acetaminophen 114
methamphetamine 074 caffeine 122
safrole 082 methyl stearate 123
C14 088 cocaine 144
34-MDA 096 methyl eicosanoate 134
34-MDMA 100 (499 min) tetraphenylethylene 162
34-MDEA 103 heroin 180
34-MDDMA 104
Method MDMA-GCS4
Instrument Gas chromatograph operated in split mode with FID
Column 1 phenyl99 methyl silicone 30 m x 025 mm x 025 microm film
thickness
Carrier gas Hydrogen at 20 mLmin
Temperature Injector 260degC
Detector 270degC
Oven program
1) 90degC initial temperature for 10 min
2) Ramp to 295degC at 30 degreesmin
3) Hold final temperature for 26 min
Injection Parameters Split Ratio = 501 1 microL injected
COMPOUND RRT COMPOUND RRT
amphetamine 053 acetaminophen 119
methamphetamine 165 caffeine 128
safrole 072 methyl stearate 153
C14 091 cocaine 160
34-MDA 094 methyl eicosanoate 167
34-MDMA 100 (436 min) tetraphenylethylene 178
34-MDEA 105 heroin 189
34-MDDMA 108
4 SEPARATION TECHNIQUES
MDMA base hydrochloride or phosphate can be separated from the matrix by solvent extraction using
the solubility data found in Section 22
5 QUANTITATIVE PROCEDURES
51 GAS CHROMATOGRAPHY
Method MDMA-GCQ1
Internal Standard Stock Solution
10 mgmL n-butylamphetamine HCl in chloroform
Standard Solution Preparation
Prepare a standard solution of MDMA HCl at 04 mgmL in chloroform
Sample Preparation
Accurately weigh out 50 mg of sample into a 25 mL volumetric flask and dilute with water to the mark Take a
2 mL aliquot of the solution add 3 mL of IS and 2-3 mL of 05 M KOH Shake Separate layers and extract
twice more with 2-3 mL each time of chloroform Combine fractions dry over sodium sulfate and dilute to
total volume of 10 mL Treat the standard in the same fashion as the sample prior to analysis
Instrument Gas chromatograph operated in split mode with FID
Column DB-1 30 m x 025 mm x 025 microm film thickness
Carrier gas Hydrogen at 13 mLmin
Make-Up gas Nitrogen at 400 mLmin
Temperatures Injector 230degC
Detector 280degC
Oven Program
1) 150degC initial temperature 2 min
2) Ramp to 190degC at 5degmin
3) Hold final temperature for 10 min
Injection Parameters Split Ratio = 201 1 microL injected
Typical Retention Time 34-MDMA 510 min
n-butylamphetamine HCl 392 min
Linear Range 006 mgmL to 20 mgmL
Repeatability RSD less than 20
Correlation Coefficient 09998
Accuracy Error less than 5
COMPOUND RRT COMPOUND RRT COMPOUND RRT
methylbenzylamine 035 methyl paraben 077 caffeine 186
P-2-P 038 salicylamide 077 antipyrine 200
amphetamine 039 penicillin 078 benzphetamine 204
nicotinic acid 042 phenmetrazine 081 diphenhydramine 214
phentermine 042 MDP-2-P 084 aminopyrine 226
methamphetamine 044 phendimetrazine 086 doxylamine 231
fenfluramine 048 MDA 087 palmitic acid 245
ethylamphetamine 049 MDMA 100 (51 min) phthalic acid 245
dimethylamphetamine 050 aminorex 105 dipyrone 251
safrole 055 methyl aminorex 105 procaine 266
salicylic acid 056 MDEA 113 eicosane 267
cathine 059 ibuprofen 124 dextromethorphan 312
phenylpropanolamine 059 MBDB 126 strychnine 317
methcathinone 060 hexadecane 128 phenyl-2-naphthalene 327
nicotinamide 062 glycerol glycolate 130 amitriptyline 334
chlorpheniramine 065 acetaminophen 135 scopolamine 371
chloroephedrine 066 MMDA 138 tetracosane 407
pseudoephedrine 066 phenacetin 141 chlordiazepoxide 431
ephedrine 068 chloro-MDMA 149 quinine 523
butylamphetamine 077 methylphenidate 163
52 HIGH PERFORMANCE LIQUID CHROMATOGRAPHY
Method MDMA-LCQ1
Standard Solution Preparation
Prepare a standard solution of MDMA at approximately 05 mgmL using water buffer or methanol
Sample Preparation
Accurately weigh an amount of sample into an appropriate volumetric or Erlenmeyer flask and dilute so
that the final MDMA concentration is approximately that of the standard solution
Instrument High performance liquid chromatograph equipped with diode array
Column 5 microm Phenomenex Luna 150 mm x 32 mm at 35C
Detector UV 210 nm
Flow 10 mLmin
Injection Volume 5 microL
Buffer 4000 mL distilled water 225 mL phosphoric acid adjust to pH 22-
23 with triethanolamine (approx 22 mL)
Mobile Phase Bufferacetonitrile 9010
Typical Retention Time 34-MDMA 1054 min
Linear Range 005 mgmL ndash 2 mgmL
Repeatability RSD less than 05
Correlation Coefficient 09999
Accuracy Error less than 5
COMPOUND RRT COMPOUND RRT
phenylpropanolamine 060 methyl aminorex 101
methyl benzylamine 062 phentermine 102
cathine 063 chloroephedrine 103
doxylamine 069 ethylamphetamine 105
dipyrone 070 MDP-2-P 105
ephedrine 072 lidocaine 107
methcathinone 073 caffeine q
pseudoephedrine 073 MDEA 113
amphetamine 084 phenyl-2-naphthalene 113
theophylline 087 phthalic acid 113
methapyrilene 089 strychnine 114
phenmetrazine 089 MMDA 117
methamphetamine 091 MBDB 125
phendimetrazine 091 salicylamide 127
COMPOUND RRT COMPOUND RRT
scopolamine 092 acetaminophen 129
MDA 093 chloro-MDMA 137
quinine 096 methylphenidate 138
saccharin 096 glycerol glycolate 148
dimethylamphetamine 097 chlorpheniramine 155
MDMA 100 (1054 min) aspirin 181
chlordiazepoxide 187
53 CAPILLARY ELECTROPHORESIS
Method MDMA-CEQ1
Internal Standard Stock Solution
050 mgmL n-butylamphetamine in 50 mM sodium phosphate at pH 70
Standard Solution Preparation
Accurately weigh and prepare a standard solution of 34-methylenedioxymethamphetamine hydrochloride at
approximately 08 mgmL using the internal standard stock solution
Sample Preparation
Accurately weigh an amount of sample into a volumetric flask and dilute with internal standard stock solution
If necessary dilute the sample so the final concentration approximates the standard concentration or falls within
the linear range Filter sample with 045-micron filter
Mode Cyclodextrin system analysis
Column 49 cm x 52 microm fused silica capillary
Run Buffer 10 mM gamma-highly sulfated cyclodextrin in 50 mM sodium phosphate
at pH 70
Detector UV 210 nm
Voltage 12 kV
Temperature 30degC air cooled
Injection 1 sec hydrodynamic at 50 mbars
Run Time 17 min
Rinse Time 20 min
Linear Range 002 - 100 mgmL
Repeatability RSD of area less than 15
Correlation Coefficient 0999
Accuracy Error less than 5
COMPOUND RRT COMPOUND RRT
d-methamphetamine 066 l-pseudoephedrine 098
d-ephedrine 074 MDMA 100 (1104 min)
MDA 080 l-ephedrine 109
cathine 085 MDEA 112
l-methamphetamine 089 MDMA 119
d-amphetamine 094 l-norephedrine 132
d-norephedrine 094 l-amphetamine 134
d-pseudoephedrine 097 MDA 136
MDEA 149
Method MDMA-CEQ2
Internal Standard Stock Solution
10 mgmL n-butylamphetamine in 38 mM phosphate buffer (pH 25)
Standard Solution Preparation
Weigh an appropriate amount of standard 34-MDMA HCl into a volumetric flask to obtain a final
concentration of approximately 008 mgmL Pipette appropriate amount of internal standard solution to obtain
a final concentration of 01 mgmL Dilute to volume with injection solvent Filter approximately 10 mL of
solution with regenerated cellulose 045 microm 25 mm filter into a 20 mL glass vial (Agilent part number 5182-
0567) Make sure there are no air bubbles on bottom of glass vial Cap vial with polypropylene cap (Agilent
part number 5182-9697)
Sample Preparation
Weigh an appropriate amount of sample into a volumetric flask so that the final phenethylamine concentration
is approximately that of the standard solution Pipette appropriate amount of internal standard solution to obtain
a final concentration of 01 mgmL Dilute to volume with injection solvent Sonicate for 15 minutes Filter
approximately 10 mL of solution with regenerated cellulose 045 microm 25 mm filter into a 20 mL glass vial
(Agilent part number 5182-0567) Make sure there are no air bubbles on bottom of glass vial Cap vial with
polypropylene cap (Agilent part number 5182-9697)
Mode HP 3D instrument operated in CE mode
Coated Capillary Mode
Column 50 microm id x 322 cm (237 cm length to detector)
Run Buffer Celixir Reagent B pH 25 (MicroSolv CE)
Detector UV 195 nm
Voltage 10 kV
Temperature 15degC
Injection 50 mbar x 2 s followed by water at 35 mbar
Run Time 6 min
Rinse Time 2 min
Linear Range 002 - 100 mgmL
Repeatability RSD lt16
Correlation Coefficient 10
Accuracy Error less than 32
COMPOUND RRT COMPOUND RRT
doxylamine 0765 ephedrine 0932
chlorpheniramine 0784 phenylephrine 0951
quinine 0804 MDEA 0961
-phenethylamine 0807 ketamine 0962
COMPOUND RRT COMPOUND RRT
chlorquinine 0812 phenyltoxolamine 0971
nicotinamide 0836 n-butylamphetamine 10(46 min)
amphetamine 0868 dextromethorphan 100
methamphetamine 0883 lidocaine 103
procaine 0883 benzocaine 125
MDA 0900 acetaminophen 211
norpseudoephedrine 0906 caffeine 214
MDMA 0914 guaifenesin 214
norephedrine 0917 P2P 224
pseudoephedrine 0919 DMSO (neutral marker) 240
tetracaine 0927 aspirin 271
54 NUCLEAR MAGNETIC RESONANCE
Method MDMA-NMR1
Solvents Deuterium Oxide (D2O) containing DSS or TSP for 0 PPM reference
Internal Standard Stock Solution (ISSS) 5 mgmL Maleic Acid (accurately weighed) in deuterium oxide (D2O)
containing DSS or TSP for 0 ppm reference
Sample Preparation Accurately weigh an amount of sample usually 10-30 mg into a capped test tube and
accurately add a volume normally 10 mL of the ISSS Vortex the sample for several seconds If insolubles
are present add 10 mL D2O (not containing maleic acid or the reference compound) vortex and sonicate 15
minutes Vortex the sample and filter if necessary Place in NMR sample tube
Instrument Varian Mercury 400 MHz with proton detection probe NMR
Spectrometer
Pulse Width 10 micros or 90deg(whichever is less)
Spectral Width (SW) at least containing ndash3 ppm through 13 ppm
Number of Scans multiple of 4 (greater to enhance signal to noise (SN))
Delay between Pulses 45 s
Shimming automatic gradient shimming of Z1-4 shims
Total run timesample 6 min (NT=4) -14 min (NT=16)
Uniformity within spectral width 03 RSD (-06 to 114 PPM)
Run Time 6 min
Linear Range 06 mgmL-60 mgmL
Repeatability lt 4
Correlation Coefficient 10
Accuracy lt 3
Compound MW Solvent Internal
Standard
Solubility
(mgmL)
Signals used for
quantitation
(position in ppm
with number of
protons) Signals in
bold and underlined
are preferred if
other numbers
present
Decompos
ition rate
(hour)
MDMA HCl 22971 D2O maleic
acid gt30
67-69 (m)(3) 60
(s)(2) 35 (sextet)(1)
30dd(1) 28dd(1)
27 (s)(3) 13 (d)(3)
lt01
MDMA
phosphate 29124 D2O
maleic
acid gt19
67-69 (m)(3) 60
(s)(2) 35 (sextet)(1)
30dd(1) 28dd(1)
27 (s)(3) 13 (d)(3)
lt01
6 QUALITATIVE DATA
See spectra on the following pages for FT-IR Vapor Phase IR FT-Raman Mass Spectrometry and Nuclear
Magnetic Resonance
7 REFERENCES
Coates J and Reffner J Visualization of Micro-ATR Infrared Spectroscopy Spectroscopy Vol 14 4
April 1999
Clarke EGC Isolation and Identification of Drugs 2nd Edition The Pharmaceutical Press 1986
Galichat Laurent Y Clarkersquos Analysis of Drugs and Poisons Volume 2 p 1256 Pharmaceutical Press 2004
Budavari S The Merck Index 13th Edition Merck and Co Inc 2001
8 ADDITIONAL RESOURCES
Forendex
Wikipedia
FTIR (KBr) 34-Methylenedioxymethamphetamine Hydrochloride
50 scans 1 nm resolution 5 mg150 mg
FTIR (diamond ATR 3 bounce) 34-Mehtylenedioxymethamphetamine Base
FTIR (1 bounce ATR) MDMA phosphate
32 scans resolution 4 cm-1
IR (Vapor Phase) 34-Methylenedioxymethamphetamine Lot A150B
2 mgmL in CH3OH
FT-RAMAN 34-Methylenedioxymethamphetamine Base
Extracted from MDMA HCl Lot A150B 32 scans 4 cm-1
resolution
FT-RAMAN 34-Methylenedioxymethamphetamine HCl
Lot A150B 32 scans 4 cm-1
resolution
19
48
26
09
34
79
36
61
45
675
34
5
60
41
66
74
71
46
77
21
81
27
88
74
10
39
6
10
97
8
11
54
7
12
47
1
12
89
61
33
69
13
60
5
13
98
01
44
19
15
02
5
16
09
41
62
88
27
93
7
29
32
72
96
79
30
37
23
07
03
33
30
5
00
05
10
15
20
25
30
35
40
45
50
55
60
65
70
75
80In
t
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
19
28
25
19
34
08
37
96
41
00
44
79
47
83
53
40
60
51
63
26
71
61
77
55
81
29
88
63
92
73
10
37
9
10
80
1
11
98
1
12
47
9
13
04
51
33
12
13
69
6
14
01
21
44
32
15
07
2
16
09
51
63
15
27
81
1
28
63
62
90
37
29
33
7
29
69
22
99
14
30
58
4
2
4
6
8
10
12
14
16
18
20
22
24
26
Int
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
FT-RAMAN 34-Methylenedioxymethamphetamine Phosphate Lot 2 TDM-275-01
32 scans 4 cm-1
resolution
Mass Spectrometry (EI) 34-Methylenedioxymethamphetamine
10
66
20
68
25
61
34
42
42
41
47
36
53
98
60
38
63
98
71
41
77
72
81
18
83
67
90
70
10
11
8
10
74
91
10
57
12
01
61
22
83
12
55
1
13
53
1
13
99
3
14
42
0
14
91
7
16
07
81
63
02
23
54
027
98
3
29
40
62
96
43
30
40
83
06
97
00
05
10
15
20
25
30
35
40
45
50
55
Int
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
Mass Spectrometry (CI) 34-Methylenedioxymethamphetamine
1H NMR MDMA base in CDCl3 with TMS 400 MHz
Extracted from MDMA HCl ndash Lot A150B
ppm 673 (d J=783 Hz 1 H) 668 (d J=117 Hz 1 H) 663 (dd J=783 117 Hz 1 H) 592 (s 2 H) 267 -
278 (ddq J=720 630 630 630 630 Hz 1 H) 261 (dd J=1350 724 Hz 1 H) 254 (dd J=1330 626
Hz 1 H) 239 (s 3 H) 104 (d J=626 Hz 3 H)
13C NMR MDMA Base
Extracted from MDMA HCl ndash Lot A 150B
1H NMR MDMA Phosphate in D2O with TSP 400 MHz
Lot 2 TDM-275-01
ppm 688 - 692 (d J=800 Hz 1 H) 686 (d J=137 Hz 1 H) 680 (dd J=800 140 Hz 1 H) 598 (s 2 H)
344 - 355 (ddq J=750 670 670 670 650 Hz 1 H) 299 (dd J=1390 650 Hz 1 H) 285 (dd J=1390
760 Hz 1 H) 270 (s 3 H) 128 (d J=665 Hz 3 H)
13C NMR MDMA Phosphate in D2O with TSP Lot 2 TDM-275-01
1H NMR MDMA Phosphate in CD3OD with TMS Lot 2 TDM-275-01
400 MHz
ppm 679 (d J=098 Hz 1 H) 678 (d J=802 Hz 1 H) 673 (dd J=800 120 Hz 1 H)
593 (s 2 H) 329 - 340 (m 1 H) 308 (dd J=1350 509 Hz 1 H) 269 (s 3 H) 267 (dd
J=1330 960 Hz 1 H) 122 (d J=646 Hz 3 H)
1H NMR MDMA HCl Lot A150B
with maleic acid as internal standard in D2O with TSP 400 MHz
ppm 688 (d J=792 Hz 1 H) 684 (d J=166 Hz 1 H) 676 - 681 (dd J=790 180 Hz 1
H) 597 (s 2 H) 341 - 354 (ddq J=770 670 670 670 650 Hz 1 H) 293 - 302 (dd
J=1400 650 Hz 1 H) 283 (dd J=1400 770 Hz 1 H) 270 (s 3 H) 127 (d J=665 Hz
3 H) Maleic acid 640 (s 2H)
1H NMR MDMA base in CD3OD with TMS
Extracted from MDMA HCl ndash Lot A150B 400 MHz
ppm 669 - 674 (d J=783 Hz 1 H) 667 (d J=137 Hz 1 H) 662 (dd J=780 140 Hz 1
H) 588 (s 2 H) 265 - 276 (m 2 H) 244 (dd J=1530 940 Hz 1 H) 234 (s 3 H) 100
(d J=606 Hz 3 H)
1H NMR MDMA HCl in CD3OD Lot A150B
400 MHz
ppm 680 (d J=160 Hz 1 H) 679 (d J=802 Hz 1 H) 674 (dd J=802 156 Hz 1 H) 593 (s 2 H) 336 -
348 (ddq J=940 650 650 650 530 Hz 1 H) 308 (dd J=1350 528 Hz 1 H) 271 (dd J=1330 940
Hz 1 H) 125 (d J=646 Hz 3 H)
13C NMR MDMA HCl in CD3OD Lot A150B
Optical isomers standards for these compounds were unavailable
No Data Available
Instrument Gas chromatograph operated in split mode with FID
Column 1 phenyl99 methyl silicone 30 m x 025 mm x 025 microm film
thickness
Carrier gas Hydrogen at 20 mLmin
Temperature Injector 260degC
Detector 270degC
Oven program
1) 90degC initial temperature for 10 min
2) Ramp to 295degC at 30 degreesmin
3) Hold final temperature for 26 min
Injection Parameters Split Ratio = 501 1 microL injected
COMPOUND RRT COMPOUND RRT
amphetamine 053 acetaminophen 119
methamphetamine 165 caffeine 128
safrole 072 methyl stearate 153
C14 091 cocaine 160
34-MDA 094 methyl eicosanoate 167
34-MDMA 100 (436 min) tetraphenylethylene 178
34-MDEA 105 heroin 189
34-MDDMA 108
4 SEPARATION TECHNIQUES
MDMA base hydrochloride or phosphate can be separated from the matrix by solvent extraction using
the solubility data found in Section 22
5 QUANTITATIVE PROCEDURES
51 GAS CHROMATOGRAPHY
Method MDMA-GCQ1
Internal Standard Stock Solution
10 mgmL n-butylamphetamine HCl in chloroform
Standard Solution Preparation
Prepare a standard solution of MDMA HCl at 04 mgmL in chloroform
Sample Preparation
Accurately weigh out 50 mg of sample into a 25 mL volumetric flask and dilute with water to the mark Take a
2 mL aliquot of the solution add 3 mL of IS and 2-3 mL of 05 M KOH Shake Separate layers and extract
twice more with 2-3 mL each time of chloroform Combine fractions dry over sodium sulfate and dilute to
total volume of 10 mL Treat the standard in the same fashion as the sample prior to analysis
Instrument Gas chromatograph operated in split mode with FID
Column DB-1 30 m x 025 mm x 025 microm film thickness
Carrier gas Hydrogen at 13 mLmin
Make-Up gas Nitrogen at 400 mLmin
Temperatures Injector 230degC
Detector 280degC
Oven Program
1) 150degC initial temperature 2 min
2) Ramp to 190degC at 5degmin
3) Hold final temperature for 10 min
Injection Parameters Split Ratio = 201 1 microL injected
Typical Retention Time 34-MDMA 510 min
n-butylamphetamine HCl 392 min
Linear Range 006 mgmL to 20 mgmL
Repeatability RSD less than 20
Correlation Coefficient 09998
Accuracy Error less than 5
COMPOUND RRT COMPOUND RRT COMPOUND RRT
methylbenzylamine 035 methyl paraben 077 caffeine 186
P-2-P 038 salicylamide 077 antipyrine 200
amphetamine 039 penicillin 078 benzphetamine 204
nicotinic acid 042 phenmetrazine 081 diphenhydramine 214
phentermine 042 MDP-2-P 084 aminopyrine 226
methamphetamine 044 phendimetrazine 086 doxylamine 231
fenfluramine 048 MDA 087 palmitic acid 245
ethylamphetamine 049 MDMA 100 (51 min) phthalic acid 245
dimethylamphetamine 050 aminorex 105 dipyrone 251
safrole 055 methyl aminorex 105 procaine 266
salicylic acid 056 MDEA 113 eicosane 267
cathine 059 ibuprofen 124 dextromethorphan 312
phenylpropanolamine 059 MBDB 126 strychnine 317
methcathinone 060 hexadecane 128 phenyl-2-naphthalene 327
nicotinamide 062 glycerol glycolate 130 amitriptyline 334
chlorpheniramine 065 acetaminophen 135 scopolamine 371
chloroephedrine 066 MMDA 138 tetracosane 407
pseudoephedrine 066 phenacetin 141 chlordiazepoxide 431
ephedrine 068 chloro-MDMA 149 quinine 523
butylamphetamine 077 methylphenidate 163
52 HIGH PERFORMANCE LIQUID CHROMATOGRAPHY
Method MDMA-LCQ1
Standard Solution Preparation
Prepare a standard solution of MDMA at approximately 05 mgmL using water buffer or methanol
Sample Preparation
Accurately weigh an amount of sample into an appropriate volumetric or Erlenmeyer flask and dilute so
that the final MDMA concentration is approximately that of the standard solution
Instrument High performance liquid chromatograph equipped with diode array
Column 5 microm Phenomenex Luna 150 mm x 32 mm at 35C
Detector UV 210 nm
Flow 10 mLmin
Injection Volume 5 microL
Buffer 4000 mL distilled water 225 mL phosphoric acid adjust to pH 22-
23 with triethanolamine (approx 22 mL)
Mobile Phase Bufferacetonitrile 9010
Typical Retention Time 34-MDMA 1054 min
Linear Range 005 mgmL ndash 2 mgmL
Repeatability RSD less than 05
Correlation Coefficient 09999
Accuracy Error less than 5
COMPOUND RRT COMPOUND RRT
phenylpropanolamine 060 methyl aminorex 101
methyl benzylamine 062 phentermine 102
cathine 063 chloroephedrine 103
doxylamine 069 ethylamphetamine 105
dipyrone 070 MDP-2-P 105
ephedrine 072 lidocaine 107
methcathinone 073 caffeine q
pseudoephedrine 073 MDEA 113
amphetamine 084 phenyl-2-naphthalene 113
theophylline 087 phthalic acid 113
methapyrilene 089 strychnine 114
phenmetrazine 089 MMDA 117
methamphetamine 091 MBDB 125
phendimetrazine 091 salicylamide 127
COMPOUND RRT COMPOUND RRT
scopolamine 092 acetaminophen 129
MDA 093 chloro-MDMA 137
quinine 096 methylphenidate 138
saccharin 096 glycerol glycolate 148
dimethylamphetamine 097 chlorpheniramine 155
MDMA 100 (1054 min) aspirin 181
chlordiazepoxide 187
53 CAPILLARY ELECTROPHORESIS
Method MDMA-CEQ1
Internal Standard Stock Solution
050 mgmL n-butylamphetamine in 50 mM sodium phosphate at pH 70
Standard Solution Preparation
Accurately weigh and prepare a standard solution of 34-methylenedioxymethamphetamine hydrochloride at
approximately 08 mgmL using the internal standard stock solution
Sample Preparation
Accurately weigh an amount of sample into a volumetric flask and dilute with internal standard stock solution
If necessary dilute the sample so the final concentration approximates the standard concentration or falls within
the linear range Filter sample with 045-micron filter
Mode Cyclodextrin system analysis
Column 49 cm x 52 microm fused silica capillary
Run Buffer 10 mM gamma-highly sulfated cyclodextrin in 50 mM sodium phosphate
at pH 70
Detector UV 210 nm
Voltage 12 kV
Temperature 30degC air cooled
Injection 1 sec hydrodynamic at 50 mbars
Run Time 17 min
Rinse Time 20 min
Linear Range 002 - 100 mgmL
Repeatability RSD of area less than 15
Correlation Coefficient 0999
Accuracy Error less than 5
COMPOUND RRT COMPOUND RRT
d-methamphetamine 066 l-pseudoephedrine 098
d-ephedrine 074 MDMA 100 (1104 min)
MDA 080 l-ephedrine 109
cathine 085 MDEA 112
l-methamphetamine 089 MDMA 119
d-amphetamine 094 l-norephedrine 132
d-norephedrine 094 l-amphetamine 134
d-pseudoephedrine 097 MDA 136
MDEA 149
Method MDMA-CEQ2
Internal Standard Stock Solution
10 mgmL n-butylamphetamine in 38 mM phosphate buffer (pH 25)
Standard Solution Preparation
Weigh an appropriate amount of standard 34-MDMA HCl into a volumetric flask to obtain a final
concentration of approximately 008 mgmL Pipette appropriate amount of internal standard solution to obtain
a final concentration of 01 mgmL Dilute to volume with injection solvent Filter approximately 10 mL of
solution with regenerated cellulose 045 microm 25 mm filter into a 20 mL glass vial (Agilent part number 5182-
0567) Make sure there are no air bubbles on bottom of glass vial Cap vial with polypropylene cap (Agilent
part number 5182-9697)
Sample Preparation
Weigh an appropriate amount of sample into a volumetric flask so that the final phenethylamine concentration
is approximately that of the standard solution Pipette appropriate amount of internal standard solution to obtain
a final concentration of 01 mgmL Dilute to volume with injection solvent Sonicate for 15 minutes Filter
approximately 10 mL of solution with regenerated cellulose 045 microm 25 mm filter into a 20 mL glass vial
(Agilent part number 5182-0567) Make sure there are no air bubbles on bottom of glass vial Cap vial with
polypropylene cap (Agilent part number 5182-9697)
Mode HP 3D instrument operated in CE mode
Coated Capillary Mode
Column 50 microm id x 322 cm (237 cm length to detector)
Run Buffer Celixir Reagent B pH 25 (MicroSolv CE)
Detector UV 195 nm
Voltage 10 kV
Temperature 15degC
Injection 50 mbar x 2 s followed by water at 35 mbar
Run Time 6 min
Rinse Time 2 min
Linear Range 002 - 100 mgmL
Repeatability RSD lt16
Correlation Coefficient 10
Accuracy Error less than 32
COMPOUND RRT COMPOUND RRT
doxylamine 0765 ephedrine 0932
chlorpheniramine 0784 phenylephrine 0951
quinine 0804 MDEA 0961
-phenethylamine 0807 ketamine 0962
COMPOUND RRT COMPOUND RRT
chlorquinine 0812 phenyltoxolamine 0971
nicotinamide 0836 n-butylamphetamine 10(46 min)
amphetamine 0868 dextromethorphan 100
methamphetamine 0883 lidocaine 103
procaine 0883 benzocaine 125
MDA 0900 acetaminophen 211
norpseudoephedrine 0906 caffeine 214
MDMA 0914 guaifenesin 214
norephedrine 0917 P2P 224
pseudoephedrine 0919 DMSO (neutral marker) 240
tetracaine 0927 aspirin 271
54 NUCLEAR MAGNETIC RESONANCE
Method MDMA-NMR1
Solvents Deuterium Oxide (D2O) containing DSS or TSP for 0 PPM reference
Internal Standard Stock Solution (ISSS) 5 mgmL Maleic Acid (accurately weighed) in deuterium oxide (D2O)
containing DSS or TSP for 0 ppm reference
Sample Preparation Accurately weigh an amount of sample usually 10-30 mg into a capped test tube and
accurately add a volume normally 10 mL of the ISSS Vortex the sample for several seconds If insolubles
are present add 10 mL D2O (not containing maleic acid or the reference compound) vortex and sonicate 15
minutes Vortex the sample and filter if necessary Place in NMR sample tube
Instrument Varian Mercury 400 MHz with proton detection probe NMR
Spectrometer
Pulse Width 10 micros or 90deg(whichever is less)
Spectral Width (SW) at least containing ndash3 ppm through 13 ppm
Number of Scans multiple of 4 (greater to enhance signal to noise (SN))
Delay between Pulses 45 s
Shimming automatic gradient shimming of Z1-4 shims
Total run timesample 6 min (NT=4) -14 min (NT=16)
Uniformity within spectral width 03 RSD (-06 to 114 PPM)
Run Time 6 min
Linear Range 06 mgmL-60 mgmL
Repeatability lt 4
Correlation Coefficient 10
Accuracy lt 3
Compound MW Solvent Internal
Standard
Solubility
(mgmL)
Signals used for
quantitation
(position in ppm
with number of
protons) Signals in
bold and underlined
are preferred if
other numbers
present
Decompos
ition rate
(hour)
MDMA HCl 22971 D2O maleic
acid gt30
67-69 (m)(3) 60
(s)(2) 35 (sextet)(1)
30dd(1) 28dd(1)
27 (s)(3) 13 (d)(3)
lt01
MDMA
phosphate 29124 D2O
maleic
acid gt19
67-69 (m)(3) 60
(s)(2) 35 (sextet)(1)
30dd(1) 28dd(1)
27 (s)(3) 13 (d)(3)
lt01
6 QUALITATIVE DATA
See spectra on the following pages for FT-IR Vapor Phase IR FT-Raman Mass Spectrometry and Nuclear
Magnetic Resonance
7 REFERENCES
Coates J and Reffner J Visualization of Micro-ATR Infrared Spectroscopy Spectroscopy Vol 14 4
April 1999
Clarke EGC Isolation and Identification of Drugs 2nd Edition The Pharmaceutical Press 1986
Galichat Laurent Y Clarkersquos Analysis of Drugs and Poisons Volume 2 p 1256 Pharmaceutical Press 2004
Budavari S The Merck Index 13th Edition Merck and Co Inc 2001
8 ADDITIONAL RESOURCES
Forendex
Wikipedia
FTIR (KBr) 34-Methylenedioxymethamphetamine Hydrochloride
50 scans 1 nm resolution 5 mg150 mg
FTIR (diamond ATR 3 bounce) 34-Mehtylenedioxymethamphetamine Base
FTIR (1 bounce ATR) MDMA phosphate
32 scans resolution 4 cm-1
IR (Vapor Phase) 34-Methylenedioxymethamphetamine Lot A150B
2 mgmL in CH3OH
FT-RAMAN 34-Methylenedioxymethamphetamine Base
Extracted from MDMA HCl Lot A150B 32 scans 4 cm-1
resolution
FT-RAMAN 34-Methylenedioxymethamphetamine HCl
Lot A150B 32 scans 4 cm-1
resolution
19
48
26
09
34
79
36
61
45
675
34
5
60
41
66
74
71
46
77
21
81
27
88
74
10
39
6
10
97
8
11
54
7
12
47
1
12
89
61
33
69
13
60
5
13
98
01
44
19
15
02
5
16
09
41
62
88
27
93
7
29
32
72
96
79
30
37
23
07
03
33
30
5
00
05
10
15
20
25
30
35
40
45
50
55
60
65
70
75
80In
t
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
19
28
25
19
34
08
37
96
41
00
44
79
47
83
53
40
60
51
63
26
71
61
77
55
81
29
88
63
92
73
10
37
9
10
80
1
11
98
1
12
47
9
13
04
51
33
12
13
69
6
14
01
21
44
32
15
07
2
16
09
51
63
15
27
81
1
28
63
62
90
37
29
33
7
29
69
22
99
14
30
58
4
2
4
6
8
10
12
14
16
18
20
22
24
26
Int
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
FT-RAMAN 34-Methylenedioxymethamphetamine Phosphate Lot 2 TDM-275-01
32 scans 4 cm-1
resolution
Mass Spectrometry (EI) 34-Methylenedioxymethamphetamine
10
66
20
68
25
61
34
42
42
41
47
36
53
98
60
38
63
98
71
41
77
72
81
18
83
67
90
70
10
11
8
10
74
91
10
57
12
01
61
22
83
12
55
1
13
53
1
13
99
3
14
42
0
14
91
7
16
07
81
63
02
23
54
027
98
3
29
40
62
96
43
30
40
83
06
97
00
05
10
15
20
25
30
35
40
45
50
55
Int
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
Mass Spectrometry (CI) 34-Methylenedioxymethamphetamine
1H NMR MDMA base in CDCl3 with TMS 400 MHz
Extracted from MDMA HCl ndash Lot A150B
ppm 673 (d J=783 Hz 1 H) 668 (d J=117 Hz 1 H) 663 (dd J=783 117 Hz 1 H) 592 (s 2 H) 267 -
278 (ddq J=720 630 630 630 630 Hz 1 H) 261 (dd J=1350 724 Hz 1 H) 254 (dd J=1330 626
Hz 1 H) 239 (s 3 H) 104 (d J=626 Hz 3 H)
13C NMR MDMA Base
Extracted from MDMA HCl ndash Lot A 150B
1H NMR MDMA Phosphate in D2O with TSP 400 MHz
Lot 2 TDM-275-01
ppm 688 - 692 (d J=800 Hz 1 H) 686 (d J=137 Hz 1 H) 680 (dd J=800 140 Hz 1 H) 598 (s 2 H)
344 - 355 (ddq J=750 670 670 670 650 Hz 1 H) 299 (dd J=1390 650 Hz 1 H) 285 (dd J=1390
760 Hz 1 H) 270 (s 3 H) 128 (d J=665 Hz 3 H)
13C NMR MDMA Phosphate in D2O with TSP Lot 2 TDM-275-01
1H NMR MDMA Phosphate in CD3OD with TMS Lot 2 TDM-275-01
400 MHz
ppm 679 (d J=098 Hz 1 H) 678 (d J=802 Hz 1 H) 673 (dd J=800 120 Hz 1 H)
593 (s 2 H) 329 - 340 (m 1 H) 308 (dd J=1350 509 Hz 1 H) 269 (s 3 H) 267 (dd
J=1330 960 Hz 1 H) 122 (d J=646 Hz 3 H)
1H NMR MDMA HCl Lot A150B
with maleic acid as internal standard in D2O with TSP 400 MHz
ppm 688 (d J=792 Hz 1 H) 684 (d J=166 Hz 1 H) 676 - 681 (dd J=790 180 Hz 1
H) 597 (s 2 H) 341 - 354 (ddq J=770 670 670 670 650 Hz 1 H) 293 - 302 (dd
J=1400 650 Hz 1 H) 283 (dd J=1400 770 Hz 1 H) 270 (s 3 H) 127 (d J=665 Hz
3 H) Maleic acid 640 (s 2H)
1H NMR MDMA base in CD3OD with TMS
Extracted from MDMA HCl ndash Lot A150B 400 MHz
ppm 669 - 674 (d J=783 Hz 1 H) 667 (d J=137 Hz 1 H) 662 (dd J=780 140 Hz 1
H) 588 (s 2 H) 265 - 276 (m 2 H) 244 (dd J=1530 940 Hz 1 H) 234 (s 3 H) 100
(d J=606 Hz 3 H)
1H NMR MDMA HCl in CD3OD Lot A150B
400 MHz
ppm 680 (d J=160 Hz 1 H) 679 (d J=802 Hz 1 H) 674 (dd J=802 156 Hz 1 H) 593 (s 2 H) 336 -
348 (ddq J=940 650 650 650 530 Hz 1 H) 308 (dd J=1350 528 Hz 1 H) 271 (dd J=1330 940
Hz 1 H) 125 (d J=646 Hz 3 H)
13C NMR MDMA HCl in CD3OD Lot A150B
Optical isomers standards for these compounds were unavailable
No Data Available
Standard Solution Preparation
Prepare a standard solution of MDMA HCl at 04 mgmL in chloroform
Sample Preparation
Accurately weigh out 50 mg of sample into a 25 mL volumetric flask and dilute with water to the mark Take a
2 mL aliquot of the solution add 3 mL of IS and 2-3 mL of 05 M KOH Shake Separate layers and extract
twice more with 2-3 mL each time of chloroform Combine fractions dry over sodium sulfate and dilute to
total volume of 10 mL Treat the standard in the same fashion as the sample prior to analysis
Instrument Gas chromatograph operated in split mode with FID
Column DB-1 30 m x 025 mm x 025 microm film thickness
Carrier gas Hydrogen at 13 mLmin
Make-Up gas Nitrogen at 400 mLmin
Temperatures Injector 230degC
Detector 280degC
Oven Program
1) 150degC initial temperature 2 min
2) Ramp to 190degC at 5degmin
3) Hold final temperature for 10 min
Injection Parameters Split Ratio = 201 1 microL injected
Typical Retention Time 34-MDMA 510 min
n-butylamphetamine HCl 392 min
Linear Range 006 mgmL to 20 mgmL
Repeatability RSD less than 20
Correlation Coefficient 09998
Accuracy Error less than 5
COMPOUND RRT COMPOUND RRT COMPOUND RRT
methylbenzylamine 035 methyl paraben 077 caffeine 186
P-2-P 038 salicylamide 077 antipyrine 200
amphetamine 039 penicillin 078 benzphetamine 204
nicotinic acid 042 phenmetrazine 081 diphenhydramine 214
phentermine 042 MDP-2-P 084 aminopyrine 226
methamphetamine 044 phendimetrazine 086 doxylamine 231
fenfluramine 048 MDA 087 palmitic acid 245
ethylamphetamine 049 MDMA 100 (51 min) phthalic acid 245
dimethylamphetamine 050 aminorex 105 dipyrone 251
safrole 055 methyl aminorex 105 procaine 266
salicylic acid 056 MDEA 113 eicosane 267
cathine 059 ibuprofen 124 dextromethorphan 312
phenylpropanolamine 059 MBDB 126 strychnine 317
methcathinone 060 hexadecane 128 phenyl-2-naphthalene 327
nicotinamide 062 glycerol glycolate 130 amitriptyline 334
chlorpheniramine 065 acetaminophen 135 scopolamine 371
chloroephedrine 066 MMDA 138 tetracosane 407
pseudoephedrine 066 phenacetin 141 chlordiazepoxide 431
ephedrine 068 chloro-MDMA 149 quinine 523
butylamphetamine 077 methylphenidate 163
52 HIGH PERFORMANCE LIQUID CHROMATOGRAPHY
Method MDMA-LCQ1
Standard Solution Preparation
Prepare a standard solution of MDMA at approximately 05 mgmL using water buffer or methanol
Sample Preparation
Accurately weigh an amount of sample into an appropriate volumetric or Erlenmeyer flask and dilute so
that the final MDMA concentration is approximately that of the standard solution
Instrument High performance liquid chromatograph equipped with diode array
Column 5 microm Phenomenex Luna 150 mm x 32 mm at 35C
Detector UV 210 nm
Flow 10 mLmin
Injection Volume 5 microL
Buffer 4000 mL distilled water 225 mL phosphoric acid adjust to pH 22-
23 with triethanolamine (approx 22 mL)
Mobile Phase Bufferacetonitrile 9010
Typical Retention Time 34-MDMA 1054 min
Linear Range 005 mgmL ndash 2 mgmL
Repeatability RSD less than 05
Correlation Coefficient 09999
Accuracy Error less than 5
COMPOUND RRT COMPOUND RRT
phenylpropanolamine 060 methyl aminorex 101
methyl benzylamine 062 phentermine 102
cathine 063 chloroephedrine 103
doxylamine 069 ethylamphetamine 105
dipyrone 070 MDP-2-P 105
ephedrine 072 lidocaine 107
methcathinone 073 caffeine q
pseudoephedrine 073 MDEA 113
amphetamine 084 phenyl-2-naphthalene 113
theophylline 087 phthalic acid 113
methapyrilene 089 strychnine 114
phenmetrazine 089 MMDA 117
methamphetamine 091 MBDB 125
phendimetrazine 091 salicylamide 127
COMPOUND RRT COMPOUND RRT
scopolamine 092 acetaminophen 129
MDA 093 chloro-MDMA 137
quinine 096 methylphenidate 138
saccharin 096 glycerol glycolate 148
dimethylamphetamine 097 chlorpheniramine 155
MDMA 100 (1054 min) aspirin 181
chlordiazepoxide 187
53 CAPILLARY ELECTROPHORESIS
Method MDMA-CEQ1
Internal Standard Stock Solution
050 mgmL n-butylamphetamine in 50 mM sodium phosphate at pH 70
Standard Solution Preparation
Accurately weigh and prepare a standard solution of 34-methylenedioxymethamphetamine hydrochloride at
approximately 08 mgmL using the internal standard stock solution
Sample Preparation
Accurately weigh an amount of sample into a volumetric flask and dilute with internal standard stock solution
If necessary dilute the sample so the final concentration approximates the standard concentration or falls within
the linear range Filter sample with 045-micron filter
Mode Cyclodextrin system analysis
Column 49 cm x 52 microm fused silica capillary
Run Buffer 10 mM gamma-highly sulfated cyclodextrin in 50 mM sodium phosphate
at pH 70
Detector UV 210 nm
Voltage 12 kV
Temperature 30degC air cooled
Injection 1 sec hydrodynamic at 50 mbars
Run Time 17 min
Rinse Time 20 min
Linear Range 002 - 100 mgmL
Repeatability RSD of area less than 15
Correlation Coefficient 0999
Accuracy Error less than 5
COMPOUND RRT COMPOUND RRT
d-methamphetamine 066 l-pseudoephedrine 098
d-ephedrine 074 MDMA 100 (1104 min)
MDA 080 l-ephedrine 109
cathine 085 MDEA 112
l-methamphetamine 089 MDMA 119
d-amphetamine 094 l-norephedrine 132
d-norephedrine 094 l-amphetamine 134
d-pseudoephedrine 097 MDA 136
MDEA 149
Method MDMA-CEQ2
Internal Standard Stock Solution
10 mgmL n-butylamphetamine in 38 mM phosphate buffer (pH 25)
Standard Solution Preparation
Weigh an appropriate amount of standard 34-MDMA HCl into a volumetric flask to obtain a final
concentration of approximately 008 mgmL Pipette appropriate amount of internal standard solution to obtain
a final concentration of 01 mgmL Dilute to volume with injection solvent Filter approximately 10 mL of
solution with regenerated cellulose 045 microm 25 mm filter into a 20 mL glass vial (Agilent part number 5182-
0567) Make sure there are no air bubbles on bottom of glass vial Cap vial with polypropylene cap (Agilent
part number 5182-9697)
Sample Preparation
Weigh an appropriate amount of sample into a volumetric flask so that the final phenethylamine concentration
is approximately that of the standard solution Pipette appropriate amount of internal standard solution to obtain
a final concentration of 01 mgmL Dilute to volume with injection solvent Sonicate for 15 minutes Filter
approximately 10 mL of solution with regenerated cellulose 045 microm 25 mm filter into a 20 mL glass vial
(Agilent part number 5182-0567) Make sure there are no air bubbles on bottom of glass vial Cap vial with
polypropylene cap (Agilent part number 5182-9697)
Mode HP 3D instrument operated in CE mode
Coated Capillary Mode
Column 50 microm id x 322 cm (237 cm length to detector)
Run Buffer Celixir Reagent B pH 25 (MicroSolv CE)
Detector UV 195 nm
Voltage 10 kV
Temperature 15degC
Injection 50 mbar x 2 s followed by water at 35 mbar
Run Time 6 min
Rinse Time 2 min
Linear Range 002 - 100 mgmL
Repeatability RSD lt16
Correlation Coefficient 10
Accuracy Error less than 32
COMPOUND RRT COMPOUND RRT
doxylamine 0765 ephedrine 0932
chlorpheniramine 0784 phenylephrine 0951
quinine 0804 MDEA 0961
-phenethylamine 0807 ketamine 0962
COMPOUND RRT COMPOUND RRT
chlorquinine 0812 phenyltoxolamine 0971
nicotinamide 0836 n-butylamphetamine 10(46 min)
amphetamine 0868 dextromethorphan 100
methamphetamine 0883 lidocaine 103
procaine 0883 benzocaine 125
MDA 0900 acetaminophen 211
norpseudoephedrine 0906 caffeine 214
MDMA 0914 guaifenesin 214
norephedrine 0917 P2P 224
pseudoephedrine 0919 DMSO (neutral marker) 240
tetracaine 0927 aspirin 271
54 NUCLEAR MAGNETIC RESONANCE
Method MDMA-NMR1
Solvents Deuterium Oxide (D2O) containing DSS or TSP for 0 PPM reference
Internal Standard Stock Solution (ISSS) 5 mgmL Maleic Acid (accurately weighed) in deuterium oxide (D2O)
containing DSS or TSP for 0 ppm reference
Sample Preparation Accurately weigh an amount of sample usually 10-30 mg into a capped test tube and
accurately add a volume normally 10 mL of the ISSS Vortex the sample for several seconds If insolubles
are present add 10 mL D2O (not containing maleic acid or the reference compound) vortex and sonicate 15
minutes Vortex the sample and filter if necessary Place in NMR sample tube
Instrument Varian Mercury 400 MHz with proton detection probe NMR
Spectrometer
Pulse Width 10 micros or 90deg(whichever is less)
Spectral Width (SW) at least containing ndash3 ppm through 13 ppm
Number of Scans multiple of 4 (greater to enhance signal to noise (SN))
Delay between Pulses 45 s
Shimming automatic gradient shimming of Z1-4 shims
Total run timesample 6 min (NT=4) -14 min (NT=16)
Uniformity within spectral width 03 RSD (-06 to 114 PPM)
Run Time 6 min
Linear Range 06 mgmL-60 mgmL
Repeatability lt 4
Correlation Coefficient 10
Accuracy lt 3
Compound MW Solvent Internal
Standard
Solubility
(mgmL)
Signals used for
quantitation
(position in ppm
with number of
protons) Signals in
bold and underlined
are preferred if
other numbers
present
Decompos
ition rate
(hour)
MDMA HCl 22971 D2O maleic
acid gt30
67-69 (m)(3) 60
(s)(2) 35 (sextet)(1)
30dd(1) 28dd(1)
27 (s)(3) 13 (d)(3)
lt01
MDMA
phosphate 29124 D2O
maleic
acid gt19
67-69 (m)(3) 60
(s)(2) 35 (sextet)(1)
30dd(1) 28dd(1)
27 (s)(3) 13 (d)(3)
lt01
6 QUALITATIVE DATA
See spectra on the following pages for FT-IR Vapor Phase IR FT-Raman Mass Spectrometry and Nuclear
Magnetic Resonance
7 REFERENCES
Coates J and Reffner J Visualization of Micro-ATR Infrared Spectroscopy Spectroscopy Vol 14 4
April 1999
Clarke EGC Isolation and Identification of Drugs 2nd Edition The Pharmaceutical Press 1986
Galichat Laurent Y Clarkersquos Analysis of Drugs and Poisons Volume 2 p 1256 Pharmaceutical Press 2004
Budavari S The Merck Index 13th Edition Merck and Co Inc 2001
8 ADDITIONAL RESOURCES
Forendex
Wikipedia
FTIR (KBr) 34-Methylenedioxymethamphetamine Hydrochloride
50 scans 1 nm resolution 5 mg150 mg
FTIR (diamond ATR 3 bounce) 34-Mehtylenedioxymethamphetamine Base
FTIR (1 bounce ATR) MDMA phosphate
32 scans resolution 4 cm-1
IR (Vapor Phase) 34-Methylenedioxymethamphetamine Lot A150B
2 mgmL in CH3OH
FT-RAMAN 34-Methylenedioxymethamphetamine Base
Extracted from MDMA HCl Lot A150B 32 scans 4 cm-1
resolution
FT-RAMAN 34-Methylenedioxymethamphetamine HCl
Lot A150B 32 scans 4 cm-1
resolution
19
48
26
09
34
79
36
61
45
675
34
5
60
41
66
74
71
46
77
21
81
27
88
74
10
39
6
10
97
8
11
54
7
12
47
1
12
89
61
33
69
13
60
5
13
98
01
44
19
15
02
5
16
09
41
62
88
27
93
7
29
32
72
96
79
30
37
23
07
03
33
30
5
00
05
10
15
20
25
30
35
40
45
50
55
60
65
70
75
80In
t
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
19
28
25
19
34
08
37
96
41
00
44
79
47
83
53
40
60
51
63
26
71
61
77
55
81
29
88
63
92
73
10
37
9
10
80
1
11
98
1
12
47
9
13
04
51
33
12
13
69
6
14
01
21
44
32
15
07
2
16
09
51
63
15
27
81
1
28
63
62
90
37
29
33
7
29
69
22
99
14
30
58
4
2
4
6
8
10
12
14
16
18
20
22
24
26
Int
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
FT-RAMAN 34-Methylenedioxymethamphetamine Phosphate Lot 2 TDM-275-01
32 scans 4 cm-1
resolution
Mass Spectrometry (EI) 34-Methylenedioxymethamphetamine
10
66
20
68
25
61
34
42
42
41
47
36
53
98
60
38
63
98
71
41
77
72
81
18
83
67
90
70
10
11
8
10
74
91
10
57
12
01
61
22
83
12
55
1
13
53
1
13
99
3
14
42
0
14
91
7
16
07
81
63
02
23
54
027
98
3
29
40
62
96
43
30
40
83
06
97
00
05
10
15
20
25
30
35
40
45
50
55
Int
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
Mass Spectrometry (CI) 34-Methylenedioxymethamphetamine
1H NMR MDMA base in CDCl3 with TMS 400 MHz
Extracted from MDMA HCl ndash Lot A150B
ppm 673 (d J=783 Hz 1 H) 668 (d J=117 Hz 1 H) 663 (dd J=783 117 Hz 1 H) 592 (s 2 H) 267 -
278 (ddq J=720 630 630 630 630 Hz 1 H) 261 (dd J=1350 724 Hz 1 H) 254 (dd J=1330 626
Hz 1 H) 239 (s 3 H) 104 (d J=626 Hz 3 H)
13C NMR MDMA Base
Extracted from MDMA HCl ndash Lot A 150B
1H NMR MDMA Phosphate in D2O with TSP 400 MHz
Lot 2 TDM-275-01
ppm 688 - 692 (d J=800 Hz 1 H) 686 (d J=137 Hz 1 H) 680 (dd J=800 140 Hz 1 H) 598 (s 2 H)
344 - 355 (ddq J=750 670 670 670 650 Hz 1 H) 299 (dd J=1390 650 Hz 1 H) 285 (dd J=1390
760 Hz 1 H) 270 (s 3 H) 128 (d J=665 Hz 3 H)
13C NMR MDMA Phosphate in D2O with TSP Lot 2 TDM-275-01
1H NMR MDMA Phosphate in CD3OD with TMS Lot 2 TDM-275-01
400 MHz
ppm 679 (d J=098 Hz 1 H) 678 (d J=802 Hz 1 H) 673 (dd J=800 120 Hz 1 H)
593 (s 2 H) 329 - 340 (m 1 H) 308 (dd J=1350 509 Hz 1 H) 269 (s 3 H) 267 (dd
J=1330 960 Hz 1 H) 122 (d J=646 Hz 3 H)
1H NMR MDMA HCl Lot A150B
with maleic acid as internal standard in D2O with TSP 400 MHz
ppm 688 (d J=792 Hz 1 H) 684 (d J=166 Hz 1 H) 676 - 681 (dd J=790 180 Hz 1
H) 597 (s 2 H) 341 - 354 (ddq J=770 670 670 670 650 Hz 1 H) 293 - 302 (dd
J=1400 650 Hz 1 H) 283 (dd J=1400 770 Hz 1 H) 270 (s 3 H) 127 (d J=665 Hz
3 H) Maleic acid 640 (s 2H)
1H NMR MDMA base in CD3OD with TMS
Extracted from MDMA HCl ndash Lot A150B 400 MHz
ppm 669 - 674 (d J=783 Hz 1 H) 667 (d J=137 Hz 1 H) 662 (dd J=780 140 Hz 1
H) 588 (s 2 H) 265 - 276 (m 2 H) 244 (dd J=1530 940 Hz 1 H) 234 (s 3 H) 100
(d J=606 Hz 3 H)
1H NMR MDMA HCl in CD3OD Lot A150B
400 MHz
ppm 680 (d J=160 Hz 1 H) 679 (d J=802 Hz 1 H) 674 (dd J=802 156 Hz 1 H) 593 (s 2 H) 336 -
348 (ddq J=940 650 650 650 530 Hz 1 H) 308 (dd J=1350 528 Hz 1 H) 271 (dd J=1330 940
Hz 1 H) 125 (d J=646 Hz 3 H)
13C NMR MDMA HCl in CD3OD Lot A150B
Optical isomers standards for these compounds were unavailable
No Data Available
nicotinic acid 042 phenmetrazine 081 diphenhydramine 214
phentermine 042 MDP-2-P 084 aminopyrine 226
methamphetamine 044 phendimetrazine 086 doxylamine 231
fenfluramine 048 MDA 087 palmitic acid 245
ethylamphetamine 049 MDMA 100 (51 min) phthalic acid 245
dimethylamphetamine 050 aminorex 105 dipyrone 251
safrole 055 methyl aminorex 105 procaine 266
salicylic acid 056 MDEA 113 eicosane 267
cathine 059 ibuprofen 124 dextromethorphan 312
phenylpropanolamine 059 MBDB 126 strychnine 317
methcathinone 060 hexadecane 128 phenyl-2-naphthalene 327
nicotinamide 062 glycerol glycolate 130 amitriptyline 334
chlorpheniramine 065 acetaminophen 135 scopolamine 371
chloroephedrine 066 MMDA 138 tetracosane 407
pseudoephedrine 066 phenacetin 141 chlordiazepoxide 431
ephedrine 068 chloro-MDMA 149 quinine 523
butylamphetamine 077 methylphenidate 163
52 HIGH PERFORMANCE LIQUID CHROMATOGRAPHY
Method MDMA-LCQ1
Standard Solution Preparation
Prepare a standard solution of MDMA at approximately 05 mgmL using water buffer or methanol
Sample Preparation
Accurately weigh an amount of sample into an appropriate volumetric or Erlenmeyer flask and dilute so
that the final MDMA concentration is approximately that of the standard solution
Instrument High performance liquid chromatograph equipped with diode array
Column 5 microm Phenomenex Luna 150 mm x 32 mm at 35C
Detector UV 210 nm
Flow 10 mLmin
Injection Volume 5 microL
Buffer 4000 mL distilled water 225 mL phosphoric acid adjust to pH 22-
23 with triethanolamine (approx 22 mL)
Mobile Phase Bufferacetonitrile 9010
Typical Retention Time 34-MDMA 1054 min
Linear Range 005 mgmL ndash 2 mgmL
Repeatability RSD less than 05
Correlation Coefficient 09999
Accuracy Error less than 5
COMPOUND RRT COMPOUND RRT
phenylpropanolamine 060 methyl aminorex 101
methyl benzylamine 062 phentermine 102
cathine 063 chloroephedrine 103
doxylamine 069 ethylamphetamine 105
dipyrone 070 MDP-2-P 105
ephedrine 072 lidocaine 107
methcathinone 073 caffeine q
pseudoephedrine 073 MDEA 113
amphetamine 084 phenyl-2-naphthalene 113
theophylline 087 phthalic acid 113
methapyrilene 089 strychnine 114
phenmetrazine 089 MMDA 117
methamphetamine 091 MBDB 125
phendimetrazine 091 salicylamide 127
COMPOUND RRT COMPOUND RRT
scopolamine 092 acetaminophen 129
MDA 093 chloro-MDMA 137
quinine 096 methylphenidate 138
saccharin 096 glycerol glycolate 148
dimethylamphetamine 097 chlorpheniramine 155
MDMA 100 (1054 min) aspirin 181
chlordiazepoxide 187
53 CAPILLARY ELECTROPHORESIS
Method MDMA-CEQ1
Internal Standard Stock Solution
050 mgmL n-butylamphetamine in 50 mM sodium phosphate at pH 70
Standard Solution Preparation
Accurately weigh and prepare a standard solution of 34-methylenedioxymethamphetamine hydrochloride at
approximately 08 mgmL using the internal standard stock solution
Sample Preparation
Accurately weigh an amount of sample into a volumetric flask and dilute with internal standard stock solution
If necessary dilute the sample so the final concentration approximates the standard concentration or falls within
the linear range Filter sample with 045-micron filter
Mode Cyclodextrin system analysis
Column 49 cm x 52 microm fused silica capillary
Run Buffer 10 mM gamma-highly sulfated cyclodextrin in 50 mM sodium phosphate
at pH 70
Detector UV 210 nm
Voltage 12 kV
Temperature 30degC air cooled
Injection 1 sec hydrodynamic at 50 mbars
Run Time 17 min
Rinse Time 20 min
Linear Range 002 - 100 mgmL
Repeatability RSD of area less than 15
Correlation Coefficient 0999
Accuracy Error less than 5
COMPOUND RRT COMPOUND RRT
d-methamphetamine 066 l-pseudoephedrine 098
d-ephedrine 074 MDMA 100 (1104 min)
MDA 080 l-ephedrine 109
cathine 085 MDEA 112
l-methamphetamine 089 MDMA 119
d-amphetamine 094 l-norephedrine 132
d-norephedrine 094 l-amphetamine 134
d-pseudoephedrine 097 MDA 136
MDEA 149
Method MDMA-CEQ2
Internal Standard Stock Solution
10 mgmL n-butylamphetamine in 38 mM phosphate buffer (pH 25)
Standard Solution Preparation
Weigh an appropriate amount of standard 34-MDMA HCl into a volumetric flask to obtain a final
concentration of approximately 008 mgmL Pipette appropriate amount of internal standard solution to obtain
a final concentration of 01 mgmL Dilute to volume with injection solvent Filter approximately 10 mL of
solution with regenerated cellulose 045 microm 25 mm filter into a 20 mL glass vial (Agilent part number 5182-
0567) Make sure there are no air bubbles on bottom of glass vial Cap vial with polypropylene cap (Agilent
part number 5182-9697)
Sample Preparation
Weigh an appropriate amount of sample into a volumetric flask so that the final phenethylamine concentration
is approximately that of the standard solution Pipette appropriate amount of internal standard solution to obtain
a final concentration of 01 mgmL Dilute to volume with injection solvent Sonicate for 15 minutes Filter
approximately 10 mL of solution with regenerated cellulose 045 microm 25 mm filter into a 20 mL glass vial
(Agilent part number 5182-0567) Make sure there are no air bubbles on bottom of glass vial Cap vial with
polypropylene cap (Agilent part number 5182-9697)
Mode HP 3D instrument operated in CE mode
Coated Capillary Mode
Column 50 microm id x 322 cm (237 cm length to detector)
Run Buffer Celixir Reagent B pH 25 (MicroSolv CE)
Detector UV 195 nm
Voltage 10 kV
Temperature 15degC
Injection 50 mbar x 2 s followed by water at 35 mbar
Run Time 6 min
Rinse Time 2 min
Linear Range 002 - 100 mgmL
Repeatability RSD lt16
Correlation Coefficient 10
Accuracy Error less than 32
COMPOUND RRT COMPOUND RRT
doxylamine 0765 ephedrine 0932
chlorpheniramine 0784 phenylephrine 0951
quinine 0804 MDEA 0961
-phenethylamine 0807 ketamine 0962
COMPOUND RRT COMPOUND RRT
chlorquinine 0812 phenyltoxolamine 0971
nicotinamide 0836 n-butylamphetamine 10(46 min)
amphetamine 0868 dextromethorphan 100
methamphetamine 0883 lidocaine 103
procaine 0883 benzocaine 125
MDA 0900 acetaminophen 211
norpseudoephedrine 0906 caffeine 214
MDMA 0914 guaifenesin 214
norephedrine 0917 P2P 224
pseudoephedrine 0919 DMSO (neutral marker) 240
tetracaine 0927 aspirin 271
54 NUCLEAR MAGNETIC RESONANCE
Method MDMA-NMR1
Solvents Deuterium Oxide (D2O) containing DSS or TSP for 0 PPM reference
Internal Standard Stock Solution (ISSS) 5 mgmL Maleic Acid (accurately weighed) in deuterium oxide (D2O)
containing DSS or TSP for 0 ppm reference
Sample Preparation Accurately weigh an amount of sample usually 10-30 mg into a capped test tube and
accurately add a volume normally 10 mL of the ISSS Vortex the sample for several seconds If insolubles
are present add 10 mL D2O (not containing maleic acid or the reference compound) vortex and sonicate 15
minutes Vortex the sample and filter if necessary Place in NMR sample tube
Instrument Varian Mercury 400 MHz with proton detection probe NMR
Spectrometer
Pulse Width 10 micros or 90deg(whichever is less)
Spectral Width (SW) at least containing ndash3 ppm through 13 ppm
Number of Scans multiple of 4 (greater to enhance signal to noise (SN))
Delay between Pulses 45 s
Shimming automatic gradient shimming of Z1-4 shims
Total run timesample 6 min (NT=4) -14 min (NT=16)
Uniformity within spectral width 03 RSD (-06 to 114 PPM)
Run Time 6 min
Linear Range 06 mgmL-60 mgmL
Repeatability lt 4
Correlation Coefficient 10
Accuracy lt 3
Compound MW Solvent Internal
Standard
Solubility
(mgmL)
Signals used for
quantitation
(position in ppm
with number of
protons) Signals in
bold and underlined
are preferred if
other numbers
present
Decompos
ition rate
(hour)
MDMA HCl 22971 D2O maleic
acid gt30
67-69 (m)(3) 60
(s)(2) 35 (sextet)(1)
30dd(1) 28dd(1)
27 (s)(3) 13 (d)(3)
lt01
MDMA
phosphate 29124 D2O
maleic
acid gt19
67-69 (m)(3) 60
(s)(2) 35 (sextet)(1)
30dd(1) 28dd(1)
27 (s)(3) 13 (d)(3)
lt01
6 QUALITATIVE DATA
See spectra on the following pages for FT-IR Vapor Phase IR FT-Raman Mass Spectrometry and Nuclear
Magnetic Resonance
7 REFERENCES
Coates J and Reffner J Visualization of Micro-ATR Infrared Spectroscopy Spectroscopy Vol 14 4
April 1999
Clarke EGC Isolation and Identification of Drugs 2nd Edition The Pharmaceutical Press 1986
Galichat Laurent Y Clarkersquos Analysis of Drugs and Poisons Volume 2 p 1256 Pharmaceutical Press 2004
Budavari S The Merck Index 13th Edition Merck and Co Inc 2001
8 ADDITIONAL RESOURCES
Forendex
Wikipedia
FTIR (KBr) 34-Methylenedioxymethamphetamine Hydrochloride
50 scans 1 nm resolution 5 mg150 mg
FTIR (diamond ATR 3 bounce) 34-Mehtylenedioxymethamphetamine Base
FTIR (1 bounce ATR) MDMA phosphate
32 scans resolution 4 cm-1
IR (Vapor Phase) 34-Methylenedioxymethamphetamine Lot A150B
2 mgmL in CH3OH
FT-RAMAN 34-Methylenedioxymethamphetamine Base
Extracted from MDMA HCl Lot A150B 32 scans 4 cm-1
resolution
FT-RAMAN 34-Methylenedioxymethamphetamine HCl
Lot A150B 32 scans 4 cm-1
resolution
19
48
26
09
34
79
36
61
45
675
34
5
60
41
66
74
71
46
77
21
81
27
88
74
10
39
6
10
97
8
11
54
7
12
47
1
12
89
61
33
69
13
60
5
13
98
01
44
19
15
02
5
16
09
41
62
88
27
93
7
29
32
72
96
79
30
37
23
07
03
33
30
5
00
05
10
15
20
25
30
35
40
45
50
55
60
65
70
75
80In
t
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
19
28
25
19
34
08
37
96
41
00
44
79
47
83
53
40
60
51
63
26
71
61
77
55
81
29
88
63
92
73
10
37
9
10
80
1
11
98
1
12
47
9
13
04
51
33
12
13
69
6
14
01
21
44
32
15
07
2
16
09
51
63
15
27
81
1
28
63
62
90
37
29
33
7
29
69
22
99
14
30
58
4
2
4
6
8
10
12
14
16
18
20
22
24
26
Int
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
FT-RAMAN 34-Methylenedioxymethamphetamine Phosphate Lot 2 TDM-275-01
32 scans 4 cm-1
resolution
Mass Spectrometry (EI) 34-Methylenedioxymethamphetamine
10
66
20
68
25
61
34
42
42
41
47
36
53
98
60
38
63
98
71
41
77
72
81
18
83
67
90
70
10
11
8
10
74
91
10
57
12
01
61
22
83
12
55
1
13
53
1
13
99
3
14
42
0
14
91
7
16
07
81
63
02
23
54
027
98
3
29
40
62
96
43
30
40
83
06
97
00
05
10
15
20
25
30
35
40
45
50
55
Int
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
Mass Spectrometry (CI) 34-Methylenedioxymethamphetamine
1H NMR MDMA base in CDCl3 with TMS 400 MHz
Extracted from MDMA HCl ndash Lot A150B
ppm 673 (d J=783 Hz 1 H) 668 (d J=117 Hz 1 H) 663 (dd J=783 117 Hz 1 H) 592 (s 2 H) 267 -
278 (ddq J=720 630 630 630 630 Hz 1 H) 261 (dd J=1350 724 Hz 1 H) 254 (dd J=1330 626
Hz 1 H) 239 (s 3 H) 104 (d J=626 Hz 3 H)
13C NMR MDMA Base
Extracted from MDMA HCl ndash Lot A 150B
1H NMR MDMA Phosphate in D2O with TSP 400 MHz
Lot 2 TDM-275-01
ppm 688 - 692 (d J=800 Hz 1 H) 686 (d J=137 Hz 1 H) 680 (dd J=800 140 Hz 1 H) 598 (s 2 H)
344 - 355 (ddq J=750 670 670 670 650 Hz 1 H) 299 (dd J=1390 650 Hz 1 H) 285 (dd J=1390
760 Hz 1 H) 270 (s 3 H) 128 (d J=665 Hz 3 H)
13C NMR MDMA Phosphate in D2O with TSP Lot 2 TDM-275-01
1H NMR MDMA Phosphate in CD3OD with TMS Lot 2 TDM-275-01
400 MHz
ppm 679 (d J=098 Hz 1 H) 678 (d J=802 Hz 1 H) 673 (dd J=800 120 Hz 1 H)
593 (s 2 H) 329 - 340 (m 1 H) 308 (dd J=1350 509 Hz 1 H) 269 (s 3 H) 267 (dd
J=1330 960 Hz 1 H) 122 (d J=646 Hz 3 H)
1H NMR MDMA HCl Lot A150B
with maleic acid as internal standard in D2O with TSP 400 MHz
ppm 688 (d J=792 Hz 1 H) 684 (d J=166 Hz 1 H) 676 - 681 (dd J=790 180 Hz 1
H) 597 (s 2 H) 341 - 354 (ddq J=770 670 670 670 650 Hz 1 H) 293 - 302 (dd
J=1400 650 Hz 1 H) 283 (dd J=1400 770 Hz 1 H) 270 (s 3 H) 127 (d J=665 Hz
3 H) Maleic acid 640 (s 2H)
1H NMR MDMA base in CD3OD with TMS
Extracted from MDMA HCl ndash Lot A150B 400 MHz
ppm 669 - 674 (d J=783 Hz 1 H) 667 (d J=137 Hz 1 H) 662 (dd J=780 140 Hz 1
H) 588 (s 2 H) 265 - 276 (m 2 H) 244 (dd J=1530 940 Hz 1 H) 234 (s 3 H) 100
(d J=606 Hz 3 H)
1H NMR MDMA HCl in CD3OD Lot A150B
400 MHz
ppm 680 (d J=160 Hz 1 H) 679 (d J=802 Hz 1 H) 674 (dd J=802 156 Hz 1 H) 593 (s 2 H) 336 -
348 (ddq J=940 650 650 650 530 Hz 1 H) 308 (dd J=1350 528 Hz 1 H) 271 (dd J=1330 940
Hz 1 H) 125 (d J=646 Hz 3 H)
13C NMR MDMA HCl in CD3OD Lot A150B
Optical isomers standards for these compounds were unavailable
No Data Available
Flow 10 mLmin
Injection Volume 5 microL
Buffer 4000 mL distilled water 225 mL phosphoric acid adjust to pH 22-
23 with triethanolamine (approx 22 mL)
Mobile Phase Bufferacetonitrile 9010
Typical Retention Time 34-MDMA 1054 min
Linear Range 005 mgmL ndash 2 mgmL
Repeatability RSD less than 05
Correlation Coefficient 09999
Accuracy Error less than 5
COMPOUND RRT COMPOUND RRT
phenylpropanolamine 060 methyl aminorex 101
methyl benzylamine 062 phentermine 102
cathine 063 chloroephedrine 103
doxylamine 069 ethylamphetamine 105
dipyrone 070 MDP-2-P 105
ephedrine 072 lidocaine 107
methcathinone 073 caffeine q
pseudoephedrine 073 MDEA 113
amphetamine 084 phenyl-2-naphthalene 113
theophylline 087 phthalic acid 113
methapyrilene 089 strychnine 114
phenmetrazine 089 MMDA 117
methamphetamine 091 MBDB 125
phendimetrazine 091 salicylamide 127
COMPOUND RRT COMPOUND RRT
scopolamine 092 acetaminophen 129
MDA 093 chloro-MDMA 137
quinine 096 methylphenidate 138
saccharin 096 glycerol glycolate 148
dimethylamphetamine 097 chlorpheniramine 155
MDMA 100 (1054 min) aspirin 181
chlordiazepoxide 187
53 CAPILLARY ELECTROPHORESIS
Method MDMA-CEQ1
Internal Standard Stock Solution
050 mgmL n-butylamphetamine in 50 mM sodium phosphate at pH 70
Standard Solution Preparation
Accurately weigh and prepare a standard solution of 34-methylenedioxymethamphetamine hydrochloride at
approximately 08 mgmL using the internal standard stock solution
Sample Preparation
Accurately weigh an amount of sample into a volumetric flask and dilute with internal standard stock solution
If necessary dilute the sample so the final concentration approximates the standard concentration or falls within
the linear range Filter sample with 045-micron filter
Mode Cyclodextrin system analysis
Column 49 cm x 52 microm fused silica capillary
Run Buffer 10 mM gamma-highly sulfated cyclodextrin in 50 mM sodium phosphate
at pH 70
Detector UV 210 nm
Voltage 12 kV
Temperature 30degC air cooled
Injection 1 sec hydrodynamic at 50 mbars
Run Time 17 min
Rinse Time 20 min
Linear Range 002 - 100 mgmL
Repeatability RSD of area less than 15
Correlation Coefficient 0999
Accuracy Error less than 5
COMPOUND RRT COMPOUND RRT
d-methamphetamine 066 l-pseudoephedrine 098
d-ephedrine 074 MDMA 100 (1104 min)
MDA 080 l-ephedrine 109
cathine 085 MDEA 112
l-methamphetamine 089 MDMA 119
d-amphetamine 094 l-norephedrine 132
d-norephedrine 094 l-amphetamine 134
d-pseudoephedrine 097 MDA 136
MDEA 149
Method MDMA-CEQ2
Internal Standard Stock Solution
10 mgmL n-butylamphetamine in 38 mM phosphate buffer (pH 25)
Standard Solution Preparation
Weigh an appropriate amount of standard 34-MDMA HCl into a volumetric flask to obtain a final
concentration of approximately 008 mgmL Pipette appropriate amount of internal standard solution to obtain
a final concentration of 01 mgmL Dilute to volume with injection solvent Filter approximately 10 mL of
solution with regenerated cellulose 045 microm 25 mm filter into a 20 mL glass vial (Agilent part number 5182-
0567) Make sure there are no air bubbles on bottom of glass vial Cap vial with polypropylene cap (Agilent
part number 5182-9697)
Sample Preparation
Weigh an appropriate amount of sample into a volumetric flask so that the final phenethylamine concentration
is approximately that of the standard solution Pipette appropriate amount of internal standard solution to obtain
a final concentration of 01 mgmL Dilute to volume with injection solvent Sonicate for 15 minutes Filter
approximately 10 mL of solution with regenerated cellulose 045 microm 25 mm filter into a 20 mL glass vial
(Agilent part number 5182-0567) Make sure there are no air bubbles on bottom of glass vial Cap vial with
polypropylene cap (Agilent part number 5182-9697)
Mode HP 3D instrument operated in CE mode
Coated Capillary Mode
Column 50 microm id x 322 cm (237 cm length to detector)
Run Buffer Celixir Reagent B pH 25 (MicroSolv CE)
Detector UV 195 nm
Voltage 10 kV
Temperature 15degC
Injection 50 mbar x 2 s followed by water at 35 mbar
Run Time 6 min
Rinse Time 2 min
Linear Range 002 - 100 mgmL
Repeatability RSD lt16
Correlation Coefficient 10
Accuracy Error less than 32
COMPOUND RRT COMPOUND RRT
doxylamine 0765 ephedrine 0932
chlorpheniramine 0784 phenylephrine 0951
quinine 0804 MDEA 0961
-phenethylamine 0807 ketamine 0962
COMPOUND RRT COMPOUND RRT
chlorquinine 0812 phenyltoxolamine 0971
nicotinamide 0836 n-butylamphetamine 10(46 min)
amphetamine 0868 dextromethorphan 100
methamphetamine 0883 lidocaine 103
procaine 0883 benzocaine 125
MDA 0900 acetaminophen 211
norpseudoephedrine 0906 caffeine 214
MDMA 0914 guaifenesin 214
norephedrine 0917 P2P 224
pseudoephedrine 0919 DMSO (neutral marker) 240
tetracaine 0927 aspirin 271
54 NUCLEAR MAGNETIC RESONANCE
Method MDMA-NMR1
Solvents Deuterium Oxide (D2O) containing DSS or TSP for 0 PPM reference
Internal Standard Stock Solution (ISSS) 5 mgmL Maleic Acid (accurately weighed) in deuterium oxide (D2O)
containing DSS or TSP for 0 ppm reference
Sample Preparation Accurately weigh an amount of sample usually 10-30 mg into a capped test tube and
accurately add a volume normally 10 mL of the ISSS Vortex the sample for several seconds If insolubles
are present add 10 mL D2O (not containing maleic acid or the reference compound) vortex and sonicate 15
minutes Vortex the sample and filter if necessary Place in NMR sample tube
Instrument Varian Mercury 400 MHz with proton detection probe NMR
Spectrometer
Pulse Width 10 micros or 90deg(whichever is less)
Spectral Width (SW) at least containing ndash3 ppm through 13 ppm
Number of Scans multiple of 4 (greater to enhance signal to noise (SN))
Delay between Pulses 45 s
Shimming automatic gradient shimming of Z1-4 shims
Total run timesample 6 min (NT=4) -14 min (NT=16)
Uniformity within spectral width 03 RSD (-06 to 114 PPM)
Run Time 6 min
Linear Range 06 mgmL-60 mgmL
Repeatability lt 4
Correlation Coefficient 10
Accuracy lt 3
Compound MW Solvent Internal
Standard
Solubility
(mgmL)
Signals used for
quantitation
(position in ppm
with number of
protons) Signals in
bold and underlined
are preferred if
other numbers
present
Decompos
ition rate
(hour)
MDMA HCl 22971 D2O maleic
acid gt30
67-69 (m)(3) 60
(s)(2) 35 (sextet)(1)
30dd(1) 28dd(1)
27 (s)(3) 13 (d)(3)
lt01
MDMA
phosphate 29124 D2O
maleic
acid gt19
67-69 (m)(3) 60
(s)(2) 35 (sextet)(1)
30dd(1) 28dd(1)
27 (s)(3) 13 (d)(3)
lt01
6 QUALITATIVE DATA
See spectra on the following pages for FT-IR Vapor Phase IR FT-Raman Mass Spectrometry and Nuclear
Magnetic Resonance
7 REFERENCES
Coates J and Reffner J Visualization of Micro-ATR Infrared Spectroscopy Spectroscopy Vol 14 4
April 1999
Clarke EGC Isolation and Identification of Drugs 2nd Edition The Pharmaceutical Press 1986
Galichat Laurent Y Clarkersquos Analysis of Drugs and Poisons Volume 2 p 1256 Pharmaceutical Press 2004
Budavari S The Merck Index 13th Edition Merck and Co Inc 2001
8 ADDITIONAL RESOURCES
Forendex
Wikipedia
FTIR (KBr) 34-Methylenedioxymethamphetamine Hydrochloride
50 scans 1 nm resolution 5 mg150 mg
FTIR (diamond ATR 3 bounce) 34-Mehtylenedioxymethamphetamine Base
FTIR (1 bounce ATR) MDMA phosphate
32 scans resolution 4 cm-1
IR (Vapor Phase) 34-Methylenedioxymethamphetamine Lot A150B
2 mgmL in CH3OH
FT-RAMAN 34-Methylenedioxymethamphetamine Base
Extracted from MDMA HCl Lot A150B 32 scans 4 cm-1
resolution
FT-RAMAN 34-Methylenedioxymethamphetamine HCl
Lot A150B 32 scans 4 cm-1
resolution
19
48
26
09
34
79
36
61
45
675
34
5
60
41
66
74
71
46
77
21
81
27
88
74
10
39
6
10
97
8
11
54
7
12
47
1
12
89
61
33
69
13
60
5
13
98
01
44
19
15
02
5
16
09
41
62
88
27
93
7
29
32
72
96
79
30
37
23
07
03
33
30
5
00
05
10
15
20
25
30
35
40
45
50
55
60
65
70
75
80In
t
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
19
28
25
19
34
08
37
96
41
00
44
79
47
83
53
40
60
51
63
26
71
61
77
55
81
29
88
63
92
73
10
37
9
10
80
1
11
98
1
12
47
9
13
04
51
33
12
13
69
6
14
01
21
44
32
15
07
2
16
09
51
63
15
27
81
1
28
63
62
90
37
29
33
7
29
69
22
99
14
30
58
4
2
4
6
8
10
12
14
16
18
20
22
24
26
Int
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
FT-RAMAN 34-Methylenedioxymethamphetamine Phosphate Lot 2 TDM-275-01
32 scans 4 cm-1
resolution
Mass Spectrometry (EI) 34-Methylenedioxymethamphetamine
10
66
20
68
25
61
34
42
42
41
47
36
53
98
60
38
63
98
71
41
77
72
81
18
83
67
90
70
10
11
8
10
74
91
10
57
12
01
61
22
83
12
55
1
13
53
1
13
99
3
14
42
0
14
91
7
16
07
81
63
02
23
54
027
98
3
29
40
62
96
43
30
40
83
06
97
00
05
10
15
20
25
30
35
40
45
50
55
Int
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
Mass Spectrometry (CI) 34-Methylenedioxymethamphetamine
1H NMR MDMA base in CDCl3 with TMS 400 MHz
Extracted from MDMA HCl ndash Lot A150B
ppm 673 (d J=783 Hz 1 H) 668 (d J=117 Hz 1 H) 663 (dd J=783 117 Hz 1 H) 592 (s 2 H) 267 -
278 (ddq J=720 630 630 630 630 Hz 1 H) 261 (dd J=1350 724 Hz 1 H) 254 (dd J=1330 626
Hz 1 H) 239 (s 3 H) 104 (d J=626 Hz 3 H)
13C NMR MDMA Base
Extracted from MDMA HCl ndash Lot A 150B
1H NMR MDMA Phosphate in D2O with TSP 400 MHz
Lot 2 TDM-275-01
ppm 688 - 692 (d J=800 Hz 1 H) 686 (d J=137 Hz 1 H) 680 (dd J=800 140 Hz 1 H) 598 (s 2 H)
344 - 355 (ddq J=750 670 670 670 650 Hz 1 H) 299 (dd J=1390 650 Hz 1 H) 285 (dd J=1390
760 Hz 1 H) 270 (s 3 H) 128 (d J=665 Hz 3 H)
13C NMR MDMA Phosphate in D2O with TSP Lot 2 TDM-275-01
1H NMR MDMA Phosphate in CD3OD with TMS Lot 2 TDM-275-01
400 MHz
ppm 679 (d J=098 Hz 1 H) 678 (d J=802 Hz 1 H) 673 (dd J=800 120 Hz 1 H)
593 (s 2 H) 329 - 340 (m 1 H) 308 (dd J=1350 509 Hz 1 H) 269 (s 3 H) 267 (dd
J=1330 960 Hz 1 H) 122 (d J=646 Hz 3 H)
1H NMR MDMA HCl Lot A150B
with maleic acid as internal standard in D2O with TSP 400 MHz
ppm 688 (d J=792 Hz 1 H) 684 (d J=166 Hz 1 H) 676 - 681 (dd J=790 180 Hz 1
H) 597 (s 2 H) 341 - 354 (ddq J=770 670 670 670 650 Hz 1 H) 293 - 302 (dd
J=1400 650 Hz 1 H) 283 (dd J=1400 770 Hz 1 H) 270 (s 3 H) 127 (d J=665 Hz
3 H) Maleic acid 640 (s 2H)
1H NMR MDMA base in CD3OD with TMS
Extracted from MDMA HCl ndash Lot A150B 400 MHz
ppm 669 - 674 (d J=783 Hz 1 H) 667 (d J=137 Hz 1 H) 662 (dd J=780 140 Hz 1
H) 588 (s 2 H) 265 - 276 (m 2 H) 244 (dd J=1530 940 Hz 1 H) 234 (s 3 H) 100
(d J=606 Hz 3 H)
1H NMR MDMA HCl in CD3OD Lot A150B
400 MHz
ppm 680 (d J=160 Hz 1 H) 679 (d J=802 Hz 1 H) 674 (dd J=802 156 Hz 1 H) 593 (s 2 H) 336 -
348 (ddq J=940 650 650 650 530 Hz 1 H) 308 (dd J=1350 528 Hz 1 H) 271 (dd J=1330 940
Hz 1 H) 125 (d J=646 Hz 3 H)
13C NMR MDMA HCl in CD3OD Lot A150B
Optical isomers standards for these compounds were unavailable
No Data Available
COMPOUND RRT COMPOUND RRT
scopolamine 092 acetaminophen 129
MDA 093 chloro-MDMA 137
quinine 096 methylphenidate 138
saccharin 096 glycerol glycolate 148
dimethylamphetamine 097 chlorpheniramine 155
MDMA 100 (1054 min) aspirin 181
chlordiazepoxide 187
53 CAPILLARY ELECTROPHORESIS
Method MDMA-CEQ1
Internal Standard Stock Solution
050 mgmL n-butylamphetamine in 50 mM sodium phosphate at pH 70
Standard Solution Preparation
Accurately weigh and prepare a standard solution of 34-methylenedioxymethamphetamine hydrochloride at
approximately 08 mgmL using the internal standard stock solution
Sample Preparation
Accurately weigh an amount of sample into a volumetric flask and dilute with internal standard stock solution
If necessary dilute the sample so the final concentration approximates the standard concentration or falls within
the linear range Filter sample with 045-micron filter
Mode Cyclodextrin system analysis
Column 49 cm x 52 microm fused silica capillary
Run Buffer 10 mM gamma-highly sulfated cyclodextrin in 50 mM sodium phosphate
at pH 70
Detector UV 210 nm
Voltage 12 kV
Temperature 30degC air cooled
Injection 1 sec hydrodynamic at 50 mbars
Run Time 17 min
Rinse Time 20 min
Linear Range 002 - 100 mgmL
Repeatability RSD of area less than 15
Correlation Coefficient 0999
Accuracy Error less than 5
COMPOUND RRT COMPOUND RRT
d-methamphetamine 066 l-pseudoephedrine 098
d-ephedrine 074 MDMA 100 (1104 min)
MDA 080 l-ephedrine 109
cathine 085 MDEA 112
l-methamphetamine 089 MDMA 119
d-amphetamine 094 l-norephedrine 132
d-norephedrine 094 l-amphetamine 134
d-pseudoephedrine 097 MDA 136
MDEA 149
Method MDMA-CEQ2
Internal Standard Stock Solution
10 mgmL n-butylamphetamine in 38 mM phosphate buffer (pH 25)
Standard Solution Preparation
Weigh an appropriate amount of standard 34-MDMA HCl into a volumetric flask to obtain a final
concentration of approximately 008 mgmL Pipette appropriate amount of internal standard solution to obtain
a final concentration of 01 mgmL Dilute to volume with injection solvent Filter approximately 10 mL of
solution with regenerated cellulose 045 microm 25 mm filter into a 20 mL glass vial (Agilent part number 5182-
0567) Make sure there are no air bubbles on bottom of glass vial Cap vial with polypropylene cap (Agilent
part number 5182-9697)
Sample Preparation
Weigh an appropriate amount of sample into a volumetric flask so that the final phenethylamine concentration
is approximately that of the standard solution Pipette appropriate amount of internal standard solution to obtain
a final concentration of 01 mgmL Dilute to volume with injection solvent Sonicate for 15 minutes Filter
approximately 10 mL of solution with regenerated cellulose 045 microm 25 mm filter into a 20 mL glass vial
(Agilent part number 5182-0567) Make sure there are no air bubbles on bottom of glass vial Cap vial with
polypropylene cap (Agilent part number 5182-9697)
Mode HP 3D instrument operated in CE mode
Coated Capillary Mode
Column 50 microm id x 322 cm (237 cm length to detector)
Run Buffer Celixir Reagent B pH 25 (MicroSolv CE)
Detector UV 195 nm
Voltage 10 kV
Temperature 15degC
Injection 50 mbar x 2 s followed by water at 35 mbar
Run Time 6 min
Rinse Time 2 min
Linear Range 002 - 100 mgmL
Repeatability RSD lt16
Correlation Coefficient 10
Accuracy Error less than 32
COMPOUND RRT COMPOUND RRT
doxylamine 0765 ephedrine 0932
chlorpheniramine 0784 phenylephrine 0951
quinine 0804 MDEA 0961
-phenethylamine 0807 ketamine 0962
COMPOUND RRT COMPOUND RRT
chlorquinine 0812 phenyltoxolamine 0971
nicotinamide 0836 n-butylamphetamine 10(46 min)
amphetamine 0868 dextromethorphan 100
methamphetamine 0883 lidocaine 103
procaine 0883 benzocaine 125
MDA 0900 acetaminophen 211
norpseudoephedrine 0906 caffeine 214
MDMA 0914 guaifenesin 214
norephedrine 0917 P2P 224
pseudoephedrine 0919 DMSO (neutral marker) 240
tetracaine 0927 aspirin 271
54 NUCLEAR MAGNETIC RESONANCE
Method MDMA-NMR1
Solvents Deuterium Oxide (D2O) containing DSS or TSP for 0 PPM reference
Internal Standard Stock Solution (ISSS) 5 mgmL Maleic Acid (accurately weighed) in deuterium oxide (D2O)
containing DSS or TSP for 0 ppm reference
Sample Preparation Accurately weigh an amount of sample usually 10-30 mg into a capped test tube and
accurately add a volume normally 10 mL of the ISSS Vortex the sample for several seconds If insolubles
are present add 10 mL D2O (not containing maleic acid or the reference compound) vortex and sonicate 15
minutes Vortex the sample and filter if necessary Place in NMR sample tube
Instrument Varian Mercury 400 MHz with proton detection probe NMR
Spectrometer
Pulse Width 10 micros or 90deg(whichever is less)
Spectral Width (SW) at least containing ndash3 ppm through 13 ppm
Number of Scans multiple of 4 (greater to enhance signal to noise (SN))
Delay between Pulses 45 s
Shimming automatic gradient shimming of Z1-4 shims
Total run timesample 6 min (NT=4) -14 min (NT=16)
Uniformity within spectral width 03 RSD (-06 to 114 PPM)
Run Time 6 min
Linear Range 06 mgmL-60 mgmL
Repeatability lt 4
Correlation Coefficient 10
Accuracy lt 3
Compound MW Solvent Internal
Standard
Solubility
(mgmL)
Signals used for
quantitation
(position in ppm
with number of
protons) Signals in
bold and underlined
are preferred if
other numbers
present
Decompos
ition rate
(hour)
MDMA HCl 22971 D2O maleic
acid gt30
67-69 (m)(3) 60
(s)(2) 35 (sextet)(1)
30dd(1) 28dd(1)
27 (s)(3) 13 (d)(3)
lt01
MDMA
phosphate 29124 D2O
maleic
acid gt19
67-69 (m)(3) 60
(s)(2) 35 (sextet)(1)
30dd(1) 28dd(1)
27 (s)(3) 13 (d)(3)
lt01
6 QUALITATIVE DATA
See spectra on the following pages for FT-IR Vapor Phase IR FT-Raman Mass Spectrometry and Nuclear
Magnetic Resonance
7 REFERENCES
Coates J and Reffner J Visualization of Micro-ATR Infrared Spectroscopy Spectroscopy Vol 14 4
April 1999
Clarke EGC Isolation and Identification of Drugs 2nd Edition The Pharmaceutical Press 1986
Galichat Laurent Y Clarkersquos Analysis of Drugs and Poisons Volume 2 p 1256 Pharmaceutical Press 2004
Budavari S The Merck Index 13th Edition Merck and Co Inc 2001
8 ADDITIONAL RESOURCES
Forendex
Wikipedia
FTIR (KBr) 34-Methylenedioxymethamphetamine Hydrochloride
50 scans 1 nm resolution 5 mg150 mg
FTIR (diamond ATR 3 bounce) 34-Mehtylenedioxymethamphetamine Base
FTIR (1 bounce ATR) MDMA phosphate
32 scans resolution 4 cm-1
IR (Vapor Phase) 34-Methylenedioxymethamphetamine Lot A150B
2 mgmL in CH3OH
FT-RAMAN 34-Methylenedioxymethamphetamine Base
Extracted from MDMA HCl Lot A150B 32 scans 4 cm-1
resolution
FT-RAMAN 34-Methylenedioxymethamphetamine HCl
Lot A150B 32 scans 4 cm-1
resolution
19
48
26
09
34
79
36
61
45
675
34
5
60
41
66
74
71
46
77
21
81
27
88
74
10
39
6
10
97
8
11
54
7
12
47
1
12
89
61
33
69
13
60
5
13
98
01
44
19
15
02
5
16
09
41
62
88
27
93
7
29
32
72
96
79
30
37
23
07
03
33
30
5
00
05
10
15
20
25
30
35
40
45
50
55
60
65
70
75
80In
t
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
19
28
25
19
34
08
37
96
41
00
44
79
47
83
53
40
60
51
63
26
71
61
77
55
81
29
88
63
92
73
10
37
9
10
80
1
11
98
1
12
47
9
13
04
51
33
12
13
69
6
14
01
21
44
32
15
07
2
16
09
51
63
15
27
81
1
28
63
62
90
37
29
33
7
29
69
22
99
14
30
58
4
2
4
6
8
10
12
14
16
18
20
22
24
26
Int
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
FT-RAMAN 34-Methylenedioxymethamphetamine Phosphate Lot 2 TDM-275-01
32 scans 4 cm-1
resolution
Mass Spectrometry (EI) 34-Methylenedioxymethamphetamine
10
66
20
68
25
61
34
42
42
41
47
36
53
98
60
38
63
98
71
41
77
72
81
18
83
67
90
70
10
11
8
10
74
91
10
57
12
01
61
22
83
12
55
1
13
53
1
13
99
3
14
42
0
14
91
7
16
07
81
63
02
23
54
027
98
3
29
40
62
96
43
30
40
83
06
97
00
05
10
15
20
25
30
35
40
45
50
55
Int
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
Mass Spectrometry (CI) 34-Methylenedioxymethamphetamine
1H NMR MDMA base in CDCl3 with TMS 400 MHz
Extracted from MDMA HCl ndash Lot A150B
ppm 673 (d J=783 Hz 1 H) 668 (d J=117 Hz 1 H) 663 (dd J=783 117 Hz 1 H) 592 (s 2 H) 267 -
278 (ddq J=720 630 630 630 630 Hz 1 H) 261 (dd J=1350 724 Hz 1 H) 254 (dd J=1330 626
Hz 1 H) 239 (s 3 H) 104 (d J=626 Hz 3 H)
13C NMR MDMA Base
Extracted from MDMA HCl ndash Lot A 150B
1H NMR MDMA Phosphate in D2O with TSP 400 MHz
Lot 2 TDM-275-01
ppm 688 - 692 (d J=800 Hz 1 H) 686 (d J=137 Hz 1 H) 680 (dd J=800 140 Hz 1 H) 598 (s 2 H)
344 - 355 (ddq J=750 670 670 670 650 Hz 1 H) 299 (dd J=1390 650 Hz 1 H) 285 (dd J=1390
760 Hz 1 H) 270 (s 3 H) 128 (d J=665 Hz 3 H)
13C NMR MDMA Phosphate in D2O with TSP Lot 2 TDM-275-01
1H NMR MDMA Phosphate in CD3OD with TMS Lot 2 TDM-275-01
400 MHz
ppm 679 (d J=098 Hz 1 H) 678 (d J=802 Hz 1 H) 673 (dd J=800 120 Hz 1 H)
593 (s 2 H) 329 - 340 (m 1 H) 308 (dd J=1350 509 Hz 1 H) 269 (s 3 H) 267 (dd
J=1330 960 Hz 1 H) 122 (d J=646 Hz 3 H)
1H NMR MDMA HCl Lot A150B
with maleic acid as internal standard in D2O with TSP 400 MHz
ppm 688 (d J=792 Hz 1 H) 684 (d J=166 Hz 1 H) 676 - 681 (dd J=790 180 Hz 1
H) 597 (s 2 H) 341 - 354 (ddq J=770 670 670 670 650 Hz 1 H) 293 - 302 (dd
J=1400 650 Hz 1 H) 283 (dd J=1400 770 Hz 1 H) 270 (s 3 H) 127 (d J=665 Hz
3 H) Maleic acid 640 (s 2H)
1H NMR MDMA base in CD3OD with TMS
Extracted from MDMA HCl ndash Lot A150B 400 MHz
ppm 669 - 674 (d J=783 Hz 1 H) 667 (d J=137 Hz 1 H) 662 (dd J=780 140 Hz 1
H) 588 (s 2 H) 265 - 276 (m 2 H) 244 (dd J=1530 940 Hz 1 H) 234 (s 3 H) 100
(d J=606 Hz 3 H)
1H NMR MDMA HCl in CD3OD Lot A150B
400 MHz
ppm 680 (d J=160 Hz 1 H) 679 (d J=802 Hz 1 H) 674 (dd J=802 156 Hz 1 H) 593 (s 2 H) 336 -
348 (ddq J=940 650 650 650 530 Hz 1 H) 308 (dd J=1350 528 Hz 1 H) 271 (dd J=1330 940
Hz 1 H) 125 (d J=646 Hz 3 H)
13C NMR MDMA HCl in CD3OD Lot A150B
Optical isomers standards for these compounds were unavailable
No Data Available
Run Time 17 min
Rinse Time 20 min
Linear Range 002 - 100 mgmL
Repeatability RSD of area less than 15
Correlation Coefficient 0999
Accuracy Error less than 5
COMPOUND RRT COMPOUND RRT
d-methamphetamine 066 l-pseudoephedrine 098
d-ephedrine 074 MDMA 100 (1104 min)
MDA 080 l-ephedrine 109
cathine 085 MDEA 112
l-methamphetamine 089 MDMA 119
d-amphetamine 094 l-norephedrine 132
d-norephedrine 094 l-amphetamine 134
d-pseudoephedrine 097 MDA 136
MDEA 149
Method MDMA-CEQ2
Internal Standard Stock Solution
10 mgmL n-butylamphetamine in 38 mM phosphate buffer (pH 25)
Standard Solution Preparation
Weigh an appropriate amount of standard 34-MDMA HCl into a volumetric flask to obtain a final
concentration of approximately 008 mgmL Pipette appropriate amount of internal standard solution to obtain
a final concentration of 01 mgmL Dilute to volume with injection solvent Filter approximately 10 mL of
solution with regenerated cellulose 045 microm 25 mm filter into a 20 mL glass vial (Agilent part number 5182-
0567) Make sure there are no air bubbles on bottom of glass vial Cap vial with polypropylene cap (Agilent
part number 5182-9697)
Sample Preparation
Weigh an appropriate amount of sample into a volumetric flask so that the final phenethylamine concentration
is approximately that of the standard solution Pipette appropriate amount of internal standard solution to obtain
a final concentration of 01 mgmL Dilute to volume with injection solvent Sonicate for 15 minutes Filter
approximately 10 mL of solution with regenerated cellulose 045 microm 25 mm filter into a 20 mL glass vial
(Agilent part number 5182-0567) Make sure there are no air bubbles on bottom of glass vial Cap vial with
polypropylene cap (Agilent part number 5182-9697)
Mode HP 3D instrument operated in CE mode
Coated Capillary Mode
Column 50 microm id x 322 cm (237 cm length to detector)
Run Buffer Celixir Reagent B pH 25 (MicroSolv CE)
Detector UV 195 nm
Voltage 10 kV
Temperature 15degC
Injection 50 mbar x 2 s followed by water at 35 mbar
Run Time 6 min
Rinse Time 2 min
Linear Range 002 - 100 mgmL
Repeatability RSD lt16
Correlation Coefficient 10
Accuracy Error less than 32
COMPOUND RRT COMPOUND RRT
doxylamine 0765 ephedrine 0932
chlorpheniramine 0784 phenylephrine 0951
quinine 0804 MDEA 0961
-phenethylamine 0807 ketamine 0962
COMPOUND RRT COMPOUND RRT
chlorquinine 0812 phenyltoxolamine 0971
nicotinamide 0836 n-butylamphetamine 10(46 min)
amphetamine 0868 dextromethorphan 100
methamphetamine 0883 lidocaine 103
procaine 0883 benzocaine 125
MDA 0900 acetaminophen 211
norpseudoephedrine 0906 caffeine 214
MDMA 0914 guaifenesin 214
norephedrine 0917 P2P 224
pseudoephedrine 0919 DMSO (neutral marker) 240
tetracaine 0927 aspirin 271
54 NUCLEAR MAGNETIC RESONANCE
Method MDMA-NMR1
Solvents Deuterium Oxide (D2O) containing DSS or TSP for 0 PPM reference
Internal Standard Stock Solution (ISSS) 5 mgmL Maleic Acid (accurately weighed) in deuterium oxide (D2O)
containing DSS or TSP for 0 ppm reference
Sample Preparation Accurately weigh an amount of sample usually 10-30 mg into a capped test tube and
accurately add a volume normally 10 mL of the ISSS Vortex the sample for several seconds If insolubles
are present add 10 mL D2O (not containing maleic acid or the reference compound) vortex and sonicate 15
minutes Vortex the sample and filter if necessary Place in NMR sample tube
Instrument Varian Mercury 400 MHz with proton detection probe NMR
Spectrometer
Pulse Width 10 micros or 90deg(whichever is less)
Spectral Width (SW) at least containing ndash3 ppm through 13 ppm
Number of Scans multiple of 4 (greater to enhance signal to noise (SN))
Delay between Pulses 45 s
Shimming automatic gradient shimming of Z1-4 shims
Total run timesample 6 min (NT=4) -14 min (NT=16)
Uniformity within spectral width 03 RSD (-06 to 114 PPM)
Run Time 6 min
Linear Range 06 mgmL-60 mgmL
Repeatability lt 4
Correlation Coefficient 10
Accuracy lt 3
Compound MW Solvent Internal
Standard
Solubility
(mgmL)
Signals used for
quantitation
(position in ppm
with number of
protons) Signals in
bold and underlined
are preferred if
other numbers
present
Decompos
ition rate
(hour)
MDMA HCl 22971 D2O maleic
acid gt30
67-69 (m)(3) 60
(s)(2) 35 (sextet)(1)
30dd(1) 28dd(1)
27 (s)(3) 13 (d)(3)
lt01
MDMA
phosphate 29124 D2O
maleic
acid gt19
67-69 (m)(3) 60
(s)(2) 35 (sextet)(1)
30dd(1) 28dd(1)
27 (s)(3) 13 (d)(3)
lt01
6 QUALITATIVE DATA
See spectra on the following pages for FT-IR Vapor Phase IR FT-Raman Mass Spectrometry and Nuclear
Magnetic Resonance
7 REFERENCES
Coates J and Reffner J Visualization of Micro-ATR Infrared Spectroscopy Spectroscopy Vol 14 4
April 1999
Clarke EGC Isolation and Identification of Drugs 2nd Edition The Pharmaceutical Press 1986
Galichat Laurent Y Clarkersquos Analysis of Drugs and Poisons Volume 2 p 1256 Pharmaceutical Press 2004
Budavari S The Merck Index 13th Edition Merck and Co Inc 2001
8 ADDITIONAL RESOURCES
Forendex
Wikipedia
FTIR (KBr) 34-Methylenedioxymethamphetamine Hydrochloride
50 scans 1 nm resolution 5 mg150 mg
FTIR (diamond ATR 3 bounce) 34-Mehtylenedioxymethamphetamine Base
FTIR (1 bounce ATR) MDMA phosphate
32 scans resolution 4 cm-1
IR (Vapor Phase) 34-Methylenedioxymethamphetamine Lot A150B
2 mgmL in CH3OH
FT-RAMAN 34-Methylenedioxymethamphetamine Base
Extracted from MDMA HCl Lot A150B 32 scans 4 cm-1
resolution
FT-RAMAN 34-Methylenedioxymethamphetamine HCl
Lot A150B 32 scans 4 cm-1
resolution
19
48
26
09
34
79
36
61
45
675
34
5
60
41
66
74
71
46
77
21
81
27
88
74
10
39
6
10
97
8
11
54
7
12
47
1
12
89
61
33
69
13
60
5
13
98
01
44
19
15
02
5
16
09
41
62
88
27
93
7
29
32
72
96
79
30
37
23
07
03
33
30
5
00
05
10
15
20
25
30
35
40
45
50
55
60
65
70
75
80In
t
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
19
28
25
19
34
08
37
96
41
00
44
79
47
83
53
40
60
51
63
26
71
61
77
55
81
29
88
63
92
73
10
37
9
10
80
1
11
98
1
12
47
9
13
04
51
33
12
13
69
6
14
01
21
44
32
15
07
2
16
09
51
63
15
27
81
1
28
63
62
90
37
29
33
7
29
69
22
99
14
30
58
4
2
4
6
8
10
12
14
16
18
20
22
24
26
Int
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
FT-RAMAN 34-Methylenedioxymethamphetamine Phosphate Lot 2 TDM-275-01
32 scans 4 cm-1
resolution
Mass Spectrometry (EI) 34-Methylenedioxymethamphetamine
10
66
20
68
25
61
34
42
42
41
47
36
53
98
60
38
63
98
71
41
77
72
81
18
83
67
90
70
10
11
8
10
74
91
10
57
12
01
61
22
83
12
55
1
13
53
1
13
99
3
14
42
0
14
91
7
16
07
81
63
02
23
54
027
98
3
29
40
62
96
43
30
40
83
06
97
00
05
10
15
20
25
30
35
40
45
50
55
Int
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
Mass Spectrometry (CI) 34-Methylenedioxymethamphetamine
1H NMR MDMA base in CDCl3 with TMS 400 MHz
Extracted from MDMA HCl ndash Lot A150B
ppm 673 (d J=783 Hz 1 H) 668 (d J=117 Hz 1 H) 663 (dd J=783 117 Hz 1 H) 592 (s 2 H) 267 -
278 (ddq J=720 630 630 630 630 Hz 1 H) 261 (dd J=1350 724 Hz 1 H) 254 (dd J=1330 626
Hz 1 H) 239 (s 3 H) 104 (d J=626 Hz 3 H)
13C NMR MDMA Base
Extracted from MDMA HCl ndash Lot A 150B
1H NMR MDMA Phosphate in D2O with TSP 400 MHz
Lot 2 TDM-275-01
ppm 688 - 692 (d J=800 Hz 1 H) 686 (d J=137 Hz 1 H) 680 (dd J=800 140 Hz 1 H) 598 (s 2 H)
344 - 355 (ddq J=750 670 670 670 650 Hz 1 H) 299 (dd J=1390 650 Hz 1 H) 285 (dd J=1390
760 Hz 1 H) 270 (s 3 H) 128 (d J=665 Hz 3 H)
13C NMR MDMA Phosphate in D2O with TSP Lot 2 TDM-275-01
1H NMR MDMA Phosphate in CD3OD with TMS Lot 2 TDM-275-01
400 MHz
ppm 679 (d J=098 Hz 1 H) 678 (d J=802 Hz 1 H) 673 (dd J=800 120 Hz 1 H)
593 (s 2 H) 329 - 340 (m 1 H) 308 (dd J=1350 509 Hz 1 H) 269 (s 3 H) 267 (dd
J=1330 960 Hz 1 H) 122 (d J=646 Hz 3 H)
1H NMR MDMA HCl Lot A150B
with maleic acid as internal standard in D2O with TSP 400 MHz
ppm 688 (d J=792 Hz 1 H) 684 (d J=166 Hz 1 H) 676 - 681 (dd J=790 180 Hz 1
H) 597 (s 2 H) 341 - 354 (ddq J=770 670 670 670 650 Hz 1 H) 293 - 302 (dd
J=1400 650 Hz 1 H) 283 (dd J=1400 770 Hz 1 H) 270 (s 3 H) 127 (d J=665 Hz
3 H) Maleic acid 640 (s 2H)
1H NMR MDMA base in CD3OD with TMS
Extracted from MDMA HCl ndash Lot A150B 400 MHz
ppm 669 - 674 (d J=783 Hz 1 H) 667 (d J=137 Hz 1 H) 662 (dd J=780 140 Hz 1
H) 588 (s 2 H) 265 - 276 (m 2 H) 244 (dd J=1530 940 Hz 1 H) 234 (s 3 H) 100
(d J=606 Hz 3 H)
1H NMR MDMA HCl in CD3OD Lot A150B
400 MHz
ppm 680 (d J=160 Hz 1 H) 679 (d J=802 Hz 1 H) 674 (dd J=802 156 Hz 1 H) 593 (s 2 H) 336 -
348 (ddq J=940 650 650 650 530 Hz 1 H) 308 (dd J=1350 528 Hz 1 H) 271 (dd J=1330 940
Hz 1 H) 125 (d J=646 Hz 3 H)
13C NMR MDMA HCl in CD3OD Lot A150B
Optical isomers standards for these compounds were unavailable
No Data Available
Weigh an appropriate amount of sample into a volumetric flask so that the final phenethylamine concentration
is approximately that of the standard solution Pipette appropriate amount of internal standard solution to obtain
a final concentration of 01 mgmL Dilute to volume with injection solvent Sonicate for 15 minutes Filter
approximately 10 mL of solution with regenerated cellulose 045 microm 25 mm filter into a 20 mL glass vial
(Agilent part number 5182-0567) Make sure there are no air bubbles on bottom of glass vial Cap vial with
polypropylene cap (Agilent part number 5182-9697)
Mode HP 3D instrument operated in CE mode
Coated Capillary Mode
Column 50 microm id x 322 cm (237 cm length to detector)
Run Buffer Celixir Reagent B pH 25 (MicroSolv CE)
Detector UV 195 nm
Voltage 10 kV
Temperature 15degC
Injection 50 mbar x 2 s followed by water at 35 mbar
Run Time 6 min
Rinse Time 2 min
Linear Range 002 - 100 mgmL
Repeatability RSD lt16
Correlation Coefficient 10
Accuracy Error less than 32
COMPOUND RRT COMPOUND RRT
doxylamine 0765 ephedrine 0932
chlorpheniramine 0784 phenylephrine 0951
quinine 0804 MDEA 0961
-phenethylamine 0807 ketamine 0962
COMPOUND RRT COMPOUND RRT
chlorquinine 0812 phenyltoxolamine 0971
nicotinamide 0836 n-butylamphetamine 10(46 min)
amphetamine 0868 dextromethorphan 100
methamphetamine 0883 lidocaine 103
procaine 0883 benzocaine 125
MDA 0900 acetaminophen 211
norpseudoephedrine 0906 caffeine 214
MDMA 0914 guaifenesin 214
norephedrine 0917 P2P 224
pseudoephedrine 0919 DMSO (neutral marker) 240
tetracaine 0927 aspirin 271
54 NUCLEAR MAGNETIC RESONANCE
Method MDMA-NMR1
Solvents Deuterium Oxide (D2O) containing DSS or TSP for 0 PPM reference
Internal Standard Stock Solution (ISSS) 5 mgmL Maleic Acid (accurately weighed) in deuterium oxide (D2O)
containing DSS or TSP for 0 ppm reference
Sample Preparation Accurately weigh an amount of sample usually 10-30 mg into a capped test tube and
accurately add a volume normally 10 mL of the ISSS Vortex the sample for several seconds If insolubles
are present add 10 mL D2O (not containing maleic acid or the reference compound) vortex and sonicate 15
minutes Vortex the sample and filter if necessary Place in NMR sample tube
Instrument Varian Mercury 400 MHz with proton detection probe NMR
Spectrometer
Pulse Width 10 micros or 90deg(whichever is less)
Spectral Width (SW) at least containing ndash3 ppm through 13 ppm
Number of Scans multiple of 4 (greater to enhance signal to noise (SN))
Delay between Pulses 45 s
Shimming automatic gradient shimming of Z1-4 shims
Total run timesample 6 min (NT=4) -14 min (NT=16)
Uniformity within spectral width 03 RSD (-06 to 114 PPM)
Run Time 6 min
Linear Range 06 mgmL-60 mgmL
Repeatability lt 4
Correlation Coefficient 10
Accuracy lt 3
Compound MW Solvent Internal
Standard
Solubility
(mgmL)
Signals used for
quantitation
(position in ppm
with number of
protons) Signals in
bold and underlined
are preferred if
other numbers
present
Decompos
ition rate
(hour)
MDMA HCl 22971 D2O maleic
acid gt30
67-69 (m)(3) 60
(s)(2) 35 (sextet)(1)
30dd(1) 28dd(1)
27 (s)(3) 13 (d)(3)
lt01
MDMA
phosphate 29124 D2O
maleic
acid gt19
67-69 (m)(3) 60
(s)(2) 35 (sextet)(1)
30dd(1) 28dd(1)
27 (s)(3) 13 (d)(3)
lt01
6 QUALITATIVE DATA
See spectra on the following pages for FT-IR Vapor Phase IR FT-Raman Mass Spectrometry and Nuclear
Magnetic Resonance
7 REFERENCES
Coates J and Reffner J Visualization of Micro-ATR Infrared Spectroscopy Spectroscopy Vol 14 4
April 1999
Clarke EGC Isolation and Identification of Drugs 2nd Edition The Pharmaceutical Press 1986
Galichat Laurent Y Clarkersquos Analysis of Drugs and Poisons Volume 2 p 1256 Pharmaceutical Press 2004
Budavari S The Merck Index 13th Edition Merck and Co Inc 2001
8 ADDITIONAL RESOURCES
Forendex
Wikipedia
FTIR (KBr) 34-Methylenedioxymethamphetamine Hydrochloride
50 scans 1 nm resolution 5 mg150 mg
FTIR (diamond ATR 3 bounce) 34-Mehtylenedioxymethamphetamine Base
FTIR (1 bounce ATR) MDMA phosphate
32 scans resolution 4 cm-1
IR (Vapor Phase) 34-Methylenedioxymethamphetamine Lot A150B
2 mgmL in CH3OH
FT-RAMAN 34-Methylenedioxymethamphetamine Base
Extracted from MDMA HCl Lot A150B 32 scans 4 cm-1
resolution
FT-RAMAN 34-Methylenedioxymethamphetamine HCl
Lot A150B 32 scans 4 cm-1
resolution
19
48
26
09
34
79
36
61
45
675
34
5
60
41
66
74
71
46
77
21
81
27
88
74
10
39
6
10
97
8
11
54
7
12
47
1
12
89
61
33
69
13
60
5
13
98
01
44
19
15
02
5
16
09
41
62
88
27
93
7
29
32
72
96
79
30
37
23
07
03
33
30
5
00
05
10
15
20
25
30
35
40
45
50
55
60
65
70
75
80In
t
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
19
28
25
19
34
08
37
96
41
00
44
79
47
83
53
40
60
51
63
26
71
61
77
55
81
29
88
63
92
73
10
37
9
10
80
1
11
98
1
12
47
9
13
04
51
33
12
13
69
6
14
01
21
44
32
15
07
2
16
09
51
63
15
27
81
1
28
63
62
90
37
29
33
7
29
69
22
99
14
30
58
4
2
4
6
8
10
12
14
16
18
20
22
24
26
Int
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
FT-RAMAN 34-Methylenedioxymethamphetamine Phosphate Lot 2 TDM-275-01
32 scans 4 cm-1
resolution
Mass Spectrometry (EI) 34-Methylenedioxymethamphetamine
10
66
20
68
25
61
34
42
42
41
47
36
53
98
60
38
63
98
71
41
77
72
81
18
83
67
90
70
10
11
8
10
74
91
10
57
12
01
61
22
83
12
55
1
13
53
1
13
99
3
14
42
0
14
91
7
16
07
81
63
02
23
54
027
98
3
29
40
62
96
43
30
40
83
06
97
00
05
10
15
20
25
30
35
40
45
50
55
Int
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
Mass Spectrometry (CI) 34-Methylenedioxymethamphetamine
1H NMR MDMA base in CDCl3 with TMS 400 MHz
Extracted from MDMA HCl ndash Lot A150B
ppm 673 (d J=783 Hz 1 H) 668 (d J=117 Hz 1 H) 663 (dd J=783 117 Hz 1 H) 592 (s 2 H) 267 -
278 (ddq J=720 630 630 630 630 Hz 1 H) 261 (dd J=1350 724 Hz 1 H) 254 (dd J=1330 626
Hz 1 H) 239 (s 3 H) 104 (d J=626 Hz 3 H)
13C NMR MDMA Base
Extracted from MDMA HCl ndash Lot A 150B
1H NMR MDMA Phosphate in D2O with TSP 400 MHz
Lot 2 TDM-275-01
ppm 688 - 692 (d J=800 Hz 1 H) 686 (d J=137 Hz 1 H) 680 (dd J=800 140 Hz 1 H) 598 (s 2 H)
344 - 355 (ddq J=750 670 670 670 650 Hz 1 H) 299 (dd J=1390 650 Hz 1 H) 285 (dd J=1390
760 Hz 1 H) 270 (s 3 H) 128 (d J=665 Hz 3 H)
13C NMR MDMA Phosphate in D2O with TSP Lot 2 TDM-275-01
1H NMR MDMA Phosphate in CD3OD with TMS Lot 2 TDM-275-01
400 MHz
ppm 679 (d J=098 Hz 1 H) 678 (d J=802 Hz 1 H) 673 (dd J=800 120 Hz 1 H)
593 (s 2 H) 329 - 340 (m 1 H) 308 (dd J=1350 509 Hz 1 H) 269 (s 3 H) 267 (dd
J=1330 960 Hz 1 H) 122 (d J=646 Hz 3 H)
1H NMR MDMA HCl Lot A150B
with maleic acid as internal standard in D2O with TSP 400 MHz
ppm 688 (d J=792 Hz 1 H) 684 (d J=166 Hz 1 H) 676 - 681 (dd J=790 180 Hz 1
H) 597 (s 2 H) 341 - 354 (ddq J=770 670 670 670 650 Hz 1 H) 293 - 302 (dd
J=1400 650 Hz 1 H) 283 (dd J=1400 770 Hz 1 H) 270 (s 3 H) 127 (d J=665 Hz
3 H) Maleic acid 640 (s 2H)
1H NMR MDMA base in CD3OD with TMS
Extracted from MDMA HCl ndash Lot A150B 400 MHz
ppm 669 - 674 (d J=783 Hz 1 H) 667 (d J=137 Hz 1 H) 662 (dd J=780 140 Hz 1
H) 588 (s 2 H) 265 - 276 (m 2 H) 244 (dd J=1530 940 Hz 1 H) 234 (s 3 H) 100
(d J=606 Hz 3 H)
1H NMR MDMA HCl in CD3OD Lot A150B
400 MHz
ppm 680 (d J=160 Hz 1 H) 679 (d J=802 Hz 1 H) 674 (dd J=802 156 Hz 1 H) 593 (s 2 H) 336 -
348 (ddq J=940 650 650 650 530 Hz 1 H) 308 (dd J=1350 528 Hz 1 H) 271 (dd J=1330 940
Hz 1 H) 125 (d J=646 Hz 3 H)
13C NMR MDMA HCl in CD3OD Lot A150B
Optical isomers standards for these compounds were unavailable
No Data Available
COMPOUND RRT COMPOUND RRT
chlorquinine 0812 phenyltoxolamine 0971
nicotinamide 0836 n-butylamphetamine 10(46 min)
amphetamine 0868 dextromethorphan 100
methamphetamine 0883 lidocaine 103
procaine 0883 benzocaine 125
MDA 0900 acetaminophen 211
norpseudoephedrine 0906 caffeine 214
MDMA 0914 guaifenesin 214
norephedrine 0917 P2P 224
pseudoephedrine 0919 DMSO (neutral marker) 240
tetracaine 0927 aspirin 271
54 NUCLEAR MAGNETIC RESONANCE
Method MDMA-NMR1
Solvents Deuterium Oxide (D2O) containing DSS or TSP for 0 PPM reference
Internal Standard Stock Solution (ISSS) 5 mgmL Maleic Acid (accurately weighed) in deuterium oxide (D2O)
containing DSS or TSP for 0 ppm reference
Sample Preparation Accurately weigh an amount of sample usually 10-30 mg into a capped test tube and
accurately add a volume normally 10 mL of the ISSS Vortex the sample for several seconds If insolubles
are present add 10 mL D2O (not containing maleic acid or the reference compound) vortex and sonicate 15
minutes Vortex the sample and filter if necessary Place in NMR sample tube
Instrument Varian Mercury 400 MHz with proton detection probe NMR
Spectrometer
Pulse Width 10 micros or 90deg(whichever is less)
Spectral Width (SW) at least containing ndash3 ppm through 13 ppm
Number of Scans multiple of 4 (greater to enhance signal to noise (SN))
Delay between Pulses 45 s
Shimming automatic gradient shimming of Z1-4 shims
Total run timesample 6 min (NT=4) -14 min (NT=16)
Uniformity within spectral width 03 RSD (-06 to 114 PPM)
Run Time 6 min
Linear Range 06 mgmL-60 mgmL
Repeatability lt 4
Correlation Coefficient 10
Accuracy lt 3
Compound MW Solvent Internal
Standard
Solubility
(mgmL)
Signals used for
quantitation
(position in ppm
with number of
protons) Signals in
bold and underlined
are preferred if
other numbers
present
Decompos
ition rate
(hour)
MDMA HCl 22971 D2O maleic
acid gt30
67-69 (m)(3) 60
(s)(2) 35 (sextet)(1)
30dd(1) 28dd(1)
27 (s)(3) 13 (d)(3)
lt01
MDMA
phosphate 29124 D2O
maleic
acid gt19
67-69 (m)(3) 60
(s)(2) 35 (sextet)(1)
30dd(1) 28dd(1)
27 (s)(3) 13 (d)(3)
lt01
6 QUALITATIVE DATA
See spectra on the following pages for FT-IR Vapor Phase IR FT-Raman Mass Spectrometry and Nuclear
Magnetic Resonance
7 REFERENCES
Coates J and Reffner J Visualization of Micro-ATR Infrared Spectroscopy Spectroscopy Vol 14 4
April 1999
Clarke EGC Isolation and Identification of Drugs 2nd Edition The Pharmaceutical Press 1986
Galichat Laurent Y Clarkersquos Analysis of Drugs and Poisons Volume 2 p 1256 Pharmaceutical Press 2004
Budavari S The Merck Index 13th Edition Merck and Co Inc 2001
8 ADDITIONAL RESOURCES
Forendex
Wikipedia
FTIR (KBr) 34-Methylenedioxymethamphetamine Hydrochloride
50 scans 1 nm resolution 5 mg150 mg
FTIR (diamond ATR 3 bounce) 34-Mehtylenedioxymethamphetamine Base
FTIR (1 bounce ATR) MDMA phosphate
32 scans resolution 4 cm-1
IR (Vapor Phase) 34-Methylenedioxymethamphetamine Lot A150B
2 mgmL in CH3OH
FT-RAMAN 34-Methylenedioxymethamphetamine Base
Extracted from MDMA HCl Lot A150B 32 scans 4 cm-1
resolution
FT-RAMAN 34-Methylenedioxymethamphetamine HCl
Lot A150B 32 scans 4 cm-1
resolution
19
48
26
09
34
79
36
61
45
675
34
5
60
41
66
74
71
46
77
21
81
27
88
74
10
39
6
10
97
8
11
54
7
12
47
1
12
89
61
33
69
13
60
5
13
98
01
44
19
15
02
5
16
09
41
62
88
27
93
7
29
32
72
96
79
30
37
23
07
03
33
30
5
00
05
10
15
20
25
30
35
40
45
50
55
60
65
70
75
80In
t
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
19
28
25
19
34
08
37
96
41
00
44
79
47
83
53
40
60
51
63
26
71
61
77
55
81
29
88
63
92
73
10
37
9
10
80
1
11
98
1
12
47
9
13
04
51
33
12
13
69
6
14
01
21
44
32
15
07
2
16
09
51
63
15
27
81
1
28
63
62
90
37
29
33
7
29
69
22
99
14
30
58
4
2
4
6
8
10
12
14
16
18
20
22
24
26
Int
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
FT-RAMAN 34-Methylenedioxymethamphetamine Phosphate Lot 2 TDM-275-01
32 scans 4 cm-1
resolution
Mass Spectrometry (EI) 34-Methylenedioxymethamphetamine
10
66
20
68
25
61
34
42
42
41
47
36
53
98
60
38
63
98
71
41
77
72
81
18
83
67
90
70
10
11
8
10
74
91
10
57
12
01
61
22
83
12
55
1
13
53
1
13
99
3
14
42
0
14
91
7
16
07
81
63
02
23
54
027
98
3
29
40
62
96
43
30
40
83
06
97
00
05
10
15
20
25
30
35
40
45
50
55
Int
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
Mass Spectrometry (CI) 34-Methylenedioxymethamphetamine
1H NMR MDMA base in CDCl3 with TMS 400 MHz
Extracted from MDMA HCl ndash Lot A150B
ppm 673 (d J=783 Hz 1 H) 668 (d J=117 Hz 1 H) 663 (dd J=783 117 Hz 1 H) 592 (s 2 H) 267 -
278 (ddq J=720 630 630 630 630 Hz 1 H) 261 (dd J=1350 724 Hz 1 H) 254 (dd J=1330 626
Hz 1 H) 239 (s 3 H) 104 (d J=626 Hz 3 H)
13C NMR MDMA Base
Extracted from MDMA HCl ndash Lot A 150B
1H NMR MDMA Phosphate in D2O with TSP 400 MHz
Lot 2 TDM-275-01
ppm 688 - 692 (d J=800 Hz 1 H) 686 (d J=137 Hz 1 H) 680 (dd J=800 140 Hz 1 H) 598 (s 2 H)
344 - 355 (ddq J=750 670 670 670 650 Hz 1 H) 299 (dd J=1390 650 Hz 1 H) 285 (dd J=1390
760 Hz 1 H) 270 (s 3 H) 128 (d J=665 Hz 3 H)
13C NMR MDMA Phosphate in D2O with TSP Lot 2 TDM-275-01
1H NMR MDMA Phosphate in CD3OD with TMS Lot 2 TDM-275-01
400 MHz
ppm 679 (d J=098 Hz 1 H) 678 (d J=802 Hz 1 H) 673 (dd J=800 120 Hz 1 H)
593 (s 2 H) 329 - 340 (m 1 H) 308 (dd J=1350 509 Hz 1 H) 269 (s 3 H) 267 (dd
J=1330 960 Hz 1 H) 122 (d J=646 Hz 3 H)
1H NMR MDMA HCl Lot A150B
with maleic acid as internal standard in D2O with TSP 400 MHz
ppm 688 (d J=792 Hz 1 H) 684 (d J=166 Hz 1 H) 676 - 681 (dd J=790 180 Hz 1
H) 597 (s 2 H) 341 - 354 (ddq J=770 670 670 670 650 Hz 1 H) 293 - 302 (dd
J=1400 650 Hz 1 H) 283 (dd J=1400 770 Hz 1 H) 270 (s 3 H) 127 (d J=665 Hz
3 H) Maleic acid 640 (s 2H)
1H NMR MDMA base in CD3OD with TMS
Extracted from MDMA HCl ndash Lot A150B 400 MHz
ppm 669 - 674 (d J=783 Hz 1 H) 667 (d J=137 Hz 1 H) 662 (dd J=780 140 Hz 1
H) 588 (s 2 H) 265 - 276 (m 2 H) 244 (dd J=1530 940 Hz 1 H) 234 (s 3 H) 100
(d J=606 Hz 3 H)
1H NMR MDMA HCl in CD3OD Lot A150B
400 MHz
ppm 680 (d J=160 Hz 1 H) 679 (d J=802 Hz 1 H) 674 (dd J=802 156 Hz 1 H) 593 (s 2 H) 336 -
348 (ddq J=940 650 650 650 530 Hz 1 H) 308 (dd J=1350 528 Hz 1 H) 271 (dd J=1330 940
Hz 1 H) 125 (d J=646 Hz 3 H)
13C NMR MDMA HCl in CD3OD Lot A150B
Optical isomers standards for these compounds were unavailable
No Data Available
Spectral Width (SW) at least containing ndash3 ppm through 13 ppm
Number of Scans multiple of 4 (greater to enhance signal to noise (SN))
Delay between Pulses 45 s
Shimming automatic gradient shimming of Z1-4 shims
Total run timesample 6 min (NT=4) -14 min (NT=16)
Uniformity within spectral width 03 RSD (-06 to 114 PPM)
Run Time 6 min
Linear Range 06 mgmL-60 mgmL
Repeatability lt 4
Correlation Coefficient 10
Accuracy lt 3
Compound MW Solvent Internal
Standard
Solubility
(mgmL)
Signals used for
quantitation
(position in ppm
with number of
protons) Signals in
bold and underlined
are preferred if
other numbers
present
Decompos
ition rate
(hour)
MDMA HCl 22971 D2O maleic
acid gt30
67-69 (m)(3) 60
(s)(2) 35 (sextet)(1)
30dd(1) 28dd(1)
27 (s)(3) 13 (d)(3)
lt01
MDMA
phosphate 29124 D2O
maleic
acid gt19
67-69 (m)(3) 60
(s)(2) 35 (sextet)(1)
30dd(1) 28dd(1)
27 (s)(3) 13 (d)(3)
lt01
6 QUALITATIVE DATA
See spectra on the following pages for FT-IR Vapor Phase IR FT-Raman Mass Spectrometry and Nuclear
Magnetic Resonance
7 REFERENCES
Coates J and Reffner J Visualization of Micro-ATR Infrared Spectroscopy Spectroscopy Vol 14 4
April 1999
Clarke EGC Isolation and Identification of Drugs 2nd Edition The Pharmaceutical Press 1986
Galichat Laurent Y Clarkersquos Analysis of Drugs and Poisons Volume 2 p 1256 Pharmaceutical Press 2004
Budavari S The Merck Index 13th Edition Merck and Co Inc 2001
8 ADDITIONAL RESOURCES
Forendex
Wikipedia
FTIR (KBr) 34-Methylenedioxymethamphetamine Hydrochloride
50 scans 1 nm resolution 5 mg150 mg
FTIR (diamond ATR 3 bounce) 34-Mehtylenedioxymethamphetamine Base
FTIR (1 bounce ATR) MDMA phosphate
32 scans resolution 4 cm-1
IR (Vapor Phase) 34-Methylenedioxymethamphetamine Lot A150B
2 mgmL in CH3OH
FT-RAMAN 34-Methylenedioxymethamphetamine Base
Extracted from MDMA HCl Lot A150B 32 scans 4 cm-1
resolution
FT-RAMAN 34-Methylenedioxymethamphetamine HCl
Lot A150B 32 scans 4 cm-1
resolution
19
48
26
09
34
79
36
61
45
675
34
5
60
41
66
74
71
46
77
21
81
27
88
74
10
39
6
10
97
8
11
54
7
12
47
1
12
89
61
33
69
13
60
5
13
98
01
44
19
15
02
5
16
09
41
62
88
27
93
7
29
32
72
96
79
30
37
23
07
03
33
30
5
00
05
10
15
20
25
30
35
40
45
50
55
60
65
70
75
80In
t
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
19
28
25
19
34
08
37
96
41
00
44
79
47
83
53
40
60
51
63
26
71
61
77
55
81
29
88
63
92
73
10
37
9
10
80
1
11
98
1
12
47
9
13
04
51
33
12
13
69
6
14
01
21
44
32
15
07
2
16
09
51
63
15
27
81
1
28
63
62
90
37
29
33
7
29
69
22
99
14
30
58
4
2
4
6
8
10
12
14
16
18
20
22
24
26
Int
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
FT-RAMAN 34-Methylenedioxymethamphetamine Phosphate Lot 2 TDM-275-01
32 scans 4 cm-1
resolution
Mass Spectrometry (EI) 34-Methylenedioxymethamphetamine
10
66
20
68
25
61
34
42
42
41
47
36
53
98
60
38
63
98
71
41
77
72
81
18
83
67
90
70
10
11
8
10
74
91
10
57
12
01
61
22
83
12
55
1
13
53
1
13
99
3
14
42
0
14
91
7
16
07
81
63
02
23
54
027
98
3
29
40
62
96
43
30
40
83
06
97
00
05
10
15
20
25
30
35
40
45
50
55
Int
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
Mass Spectrometry (CI) 34-Methylenedioxymethamphetamine
1H NMR MDMA base in CDCl3 with TMS 400 MHz
Extracted from MDMA HCl ndash Lot A150B
ppm 673 (d J=783 Hz 1 H) 668 (d J=117 Hz 1 H) 663 (dd J=783 117 Hz 1 H) 592 (s 2 H) 267 -
278 (ddq J=720 630 630 630 630 Hz 1 H) 261 (dd J=1350 724 Hz 1 H) 254 (dd J=1330 626
Hz 1 H) 239 (s 3 H) 104 (d J=626 Hz 3 H)
13C NMR MDMA Base
Extracted from MDMA HCl ndash Lot A 150B
1H NMR MDMA Phosphate in D2O with TSP 400 MHz
Lot 2 TDM-275-01
ppm 688 - 692 (d J=800 Hz 1 H) 686 (d J=137 Hz 1 H) 680 (dd J=800 140 Hz 1 H) 598 (s 2 H)
344 - 355 (ddq J=750 670 670 670 650 Hz 1 H) 299 (dd J=1390 650 Hz 1 H) 285 (dd J=1390
760 Hz 1 H) 270 (s 3 H) 128 (d J=665 Hz 3 H)
13C NMR MDMA Phosphate in D2O with TSP Lot 2 TDM-275-01
1H NMR MDMA Phosphate in CD3OD with TMS Lot 2 TDM-275-01
400 MHz
ppm 679 (d J=098 Hz 1 H) 678 (d J=802 Hz 1 H) 673 (dd J=800 120 Hz 1 H)
593 (s 2 H) 329 - 340 (m 1 H) 308 (dd J=1350 509 Hz 1 H) 269 (s 3 H) 267 (dd
J=1330 960 Hz 1 H) 122 (d J=646 Hz 3 H)
1H NMR MDMA HCl Lot A150B
with maleic acid as internal standard in D2O with TSP 400 MHz
ppm 688 (d J=792 Hz 1 H) 684 (d J=166 Hz 1 H) 676 - 681 (dd J=790 180 Hz 1
H) 597 (s 2 H) 341 - 354 (ddq J=770 670 670 670 650 Hz 1 H) 293 - 302 (dd
J=1400 650 Hz 1 H) 283 (dd J=1400 770 Hz 1 H) 270 (s 3 H) 127 (d J=665 Hz
3 H) Maleic acid 640 (s 2H)
1H NMR MDMA base in CD3OD with TMS
Extracted from MDMA HCl ndash Lot A150B 400 MHz
ppm 669 - 674 (d J=783 Hz 1 H) 667 (d J=137 Hz 1 H) 662 (dd J=780 140 Hz 1
H) 588 (s 2 H) 265 - 276 (m 2 H) 244 (dd J=1530 940 Hz 1 H) 234 (s 3 H) 100
(d J=606 Hz 3 H)
1H NMR MDMA HCl in CD3OD Lot A150B
400 MHz
ppm 680 (d J=160 Hz 1 H) 679 (d J=802 Hz 1 H) 674 (dd J=802 156 Hz 1 H) 593 (s 2 H) 336 -
348 (ddq J=940 650 650 650 530 Hz 1 H) 308 (dd J=1350 528 Hz 1 H) 271 (dd J=1330 940
Hz 1 H) 125 (d J=646 Hz 3 H)
13C NMR MDMA HCl in CD3OD Lot A150B
Optical isomers standards for these compounds were unavailable
No Data Available
See spectra on the following pages for FT-IR Vapor Phase IR FT-Raman Mass Spectrometry and Nuclear
Magnetic Resonance
7 REFERENCES
Coates J and Reffner J Visualization of Micro-ATR Infrared Spectroscopy Spectroscopy Vol 14 4
April 1999
Clarke EGC Isolation and Identification of Drugs 2nd Edition The Pharmaceutical Press 1986
Galichat Laurent Y Clarkersquos Analysis of Drugs and Poisons Volume 2 p 1256 Pharmaceutical Press 2004
Budavari S The Merck Index 13th Edition Merck and Co Inc 2001
8 ADDITIONAL RESOURCES
Forendex
Wikipedia
FTIR (KBr) 34-Methylenedioxymethamphetamine Hydrochloride
50 scans 1 nm resolution 5 mg150 mg
FTIR (diamond ATR 3 bounce) 34-Mehtylenedioxymethamphetamine Base
FTIR (1 bounce ATR) MDMA phosphate
32 scans resolution 4 cm-1
IR (Vapor Phase) 34-Methylenedioxymethamphetamine Lot A150B
2 mgmL in CH3OH
FT-RAMAN 34-Methylenedioxymethamphetamine Base
Extracted from MDMA HCl Lot A150B 32 scans 4 cm-1
resolution
FT-RAMAN 34-Methylenedioxymethamphetamine HCl
Lot A150B 32 scans 4 cm-1
resolution
19
48
26
09
34
79
36
61
45
675
34
5
60
41
66
74
71
46
77
21
81
27
88
74
10
39
6
10
97
8
11
54
7
12
47
1
12
89
61
33
69
13
60
5
13
98
01
44
19
15
02
5
16
09
41
62
88
27
93
7
29
32
72
96
79
30
37
23
07
03
33
30
5
00
05
10
15
20
25
30
35
40
45
50
55
60
65
70
75
80In
t
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
19
28
25
19
34
08
37
96
41
00
44
79
47
83
53
40
60
51
63
26
71
61
77
55
81
29
88
63
92
73
10
37
9
10
80
1
11
98
1
12
47
9
13
04
51
33
12
13
69
6
14
01
21
44
32
15
07
2
16
09
51
63
15
27
81
1
28
63
62
90
37
29
33
7
29
69
22
99
14
30
58
4
2
4
6
8
10
12
14
16
18
20
22
24
26
Int
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
FT-RAMAN 34-Methylenedioxymethamphetamine Phosphate Lot 2 TDM-275-01
32 scans 4 cm-1
resolution
Mass Spectrometry (EI) 34-Methylenedioxymethamphetamine
10
66
20
68
25
61
34
42
42
41
47
36
53
98
60
38
63
98
71
41
77
72
81
18
83
67
90
70
10
11
8
10
74
91
10
57
12
01
61
22
83
12
55
1
13
53
1
13
99
3
14
42
0
14
91
7
16
07
81
63
02
23
54
027
98
3
29
40
62
96
43
30
40
83
06
97
00
05
10
15
20
25
30
35
40
45
50
55
Int
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
Mass Spectrometry (CI) 34-Methylenedioxymethamphetamine
1H NMR MDMA base in CDCl3 with TMS 400 MHz
Extracted from MDMA HCl ndash Lot A150B
ppm 673 (d J=783 Hz 1 H) 668 (d J=117 Hz 1 H) 663 (dd J=783 117 Hz 1 H) 592 (s 2 H) 267 -
278 (ddq J=720 630 630 630 630 Hz 1 H) 261 (dd J=1350 724 Hz 1 H) 254 (dd J=1330 626
Hz 1 H) 239 (s 3 H) 104 (d J=626 Hz 3 H)
13C NMR MDMA Base
Extracted from MDMA HCl ndash Lot A 150B
1H NMR MDMA Phosphate in D2O with TSP 400 MHz
Lot 2 TDM-275-01
ppm 688 - 692 (d J=800 Hz 1 H) 686 (d J=137 Hz 1 H) 680 (dd J=800 140 Hz 1 H) 598 (s 2 H)
344 - 355 (ddq J=750 670 670 670 650 Hz 1 H) 299 (dd J=1390 650 Hz 1 H) 285 (dd J=1390
760 Hz 1 H) 270 (s 3 H) 128 (d J=665 Hz 3 H)
13C NMR MDMA Phosphate in D2O with TSP Lot 2 TDM-275-01
1H NMR MDMA Phosphate in CD3OD with TMS Lot 2 TDM-275-01
400 MHz
ppm 679 (d J=098 Hz 1 H) 678 (d J=802 Hz 1 H) 673 (dd J=800 120 Hz 1 H)
593 (s 2 H) 329 - 340 (m 1 H) 308 (dd J=1350 509 Hz 1 H) 269 (s 3 H) 267 (dd
J=1330 960 Hz 1 H) 122 (d J=646 Hz 3 H)
1H NMR MDMA HCl Lot A150B
with maleic acid as internal standard in D2O with TSP 400 MHz
ppm 688 (d J=792 Hz 1 H) 684 (d J=166 Hz 1 H) 676 - 681 (dd J=790 180 Hz 1
H) 597 (s 2 H) 341 - 354 (ddq J=770 670 670 670 650 Hz 1 H) 293 - 302 (dd
J=1400 650 Hz 1 H) 283 (dd J=1400 770 Hz 1 H) 270 (s 3 H) 127 (d J=665 Hz
3 H) Maleic acid 640 (s 2H)
1H NMR MDMA base in CD3OD with TMS
Extracted from MDMA HCl ndash Lot A150B 400 MHz
ppm 669 - 674 (d J=783 Hz 1 H) 667 (d J=137 Hz 1 H) 662 (dd J=780 140 Hz 1
H) 588 (s 2 H) 265 - 276 (m 2 H) 244 (dd J=1530 940 Hz 1 H) 234 (s 3 H) 100
(d J=606 Hz 3 H)
1H NMR MDMA HCl in CD3OD Lot A150B
400 MHz
ppm 680 (d J=160 Hz 1 H) 679 (d J=802 Hz 1 H) 674 (dd J=802 156 Hz 1 H) 593 (s 2 H) 336 -
348 (ddq J=940 650 650 650 530 Hz 1 H) 308 (dd J=1350 528 Hz 1 H) 271 (dd J=1330 940
Hz 1 H) 125 (d J=646 Hz 3 H)
13C NMR MDMA HCl in CD3OD Lot A150B
Optical isomers standards for these compounds were unavailable
No Data Available
FTIR (KBr) 34-Methylenedioxymethamphetamine Hydrochloride
50 scans 1 nm resolution 5 mg150 mg
FTIR (diamond ATR 3 bounce) 34-Mehtylenedioxymethamphetamine Base
FTIR (1 bounce ATR) MDMA phosphate
32 scans resolution 4 cm-1
IR (Vapor Phase) 34-Methylenedioxymethamphetamine Lot A150B
2 mgmL in CH3OH
FT-RAMAN 34-Methylenedioxymethamphetamine Base
Extracted from MDMA HCl Lot A150B 32 scans 4 cm-1
resolution
FT-RAMAN 34-Methylenedioxymethamphetamine HCl
Lot A150B 32 scans 4 cm-1
resolution
19
48
26
09
34
79
36
61
45
675
34
5
60
41
66
74
71
46
77
21
81
27
88
74
10
39
6
10
97
8
11
54
7
12
47
1
12
89
61
33
69
13
60
5
13
98
01
44
19
15
02
5
16
09
41
62
88
27
93
7
29
32
72
96
79
30
37
23
07
03
33
30
5
00
05
10
15
20
25
30
35
40
45
50
55
60
65
70
75
80In
t
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
19
28
25
19
34
08
37
96
41
00
44
79
47
83
53
40
60
51
63
26
71
61
77
55
81
29
88
63
92
73
10
37
9
10
80
1
11
98
1
12
47
9
13
04
51
33
12
13
69
6
14
01
21
44
32
15
07
2
16
09
51
63
15
27
81
1
28
63
62
90
37
29
33
7
29
69
22
99
14
30
58
4
2
4
6
8
10
12
14
16
18
20
22
24
26
Int
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
FT-RAMAN 34-Methylenedioxymethamphetamine Phosphate Lot 2 TDM-275-01
32 scans 4 cm-1
resolution
Mass Spectrometry (EI) 34-Methylenedioxymethamphetamine
10
66
20
68
25
61
34
42
42
41
47
36
53
98
60
38
63
98
71
41
77
72
81
18
83
67
90
70
10
11
8
10
74
91
10
57
12
01
61
22
83
12
55
1
13
53
1
13
99
3
14
42
0
14
91
7
16
07
81
63
02
23
54
027
98
3
29
40
62
96
43
30
40
83
06
97
00
05
10
15
20
25
30
35
40
45
50
55
Int
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
Mass Spectrometry (CI) 34-Methylenedioxymethamphetamine
1H NMR MDMA base in CDCl3 with TMS 400 MHz
Extracted from MDMA HCl ndash Lot A150B
ppm 673 (d J=783 Hz 1 H) 668 (d J=117 Hz 1 H) 663 (dd J=783 117 Hz 1 H) 592 (s 2 H) 267 -
278 (ddq J=720 630 630 630 630 Hz 1 H) 261 (dd J=1350 724 Hz 1 H) 254 (dd J=1330 626
Hz 1 H) 239 (s 3 H) 104 (d J=626 Hz 3 H)
13C NMR MDMA Base
Extracted from MDMA HCl ndash Lot A 150B
1H NMR MDMA Phosphate in D2O with TSP 400 MHz
Lot 2 TDM-275-01
ppm 688 - 692 (d J=800 Hz 1 H) 686 (d J=137 Hz 1 H) 680 (dd J=800 140 Hz 1 H) 598 (s 2 H)
344 - 355 (ddq J=750 670 670 670 650 Hz 1 H) 299 (dd J=1390 650 Hz 1 H) 285 (dd J=1390
760 Hz 1 H) 270 (s 3 H) 128 (d J=665 Hz 3 H)
13C NMR MDMA Phosphate in D2O with TSP Lot 2 TDM-275-01
1H NMR MDMA Phosphate in CD3OD with TMS Lot 2 TDM-275-01
400 MHz
ppm 679 (d J=098 Hz 1 H) 678 (d J=802 Hz 1 H) 673 (dd J=800 120 Hz 1 H)
593 (s 2 H) 329 - 340 (m 1 H) 308 (dd J=1350 509 Hz 1 H) 269 (s 3 H) 267 (dd
J=1330 960 Hz 1 H) 122 (d J=646 Hz 3 H)
1H NMR MDMA HCl Lot A150B
with maleic acid as internal standard in D2O with TSP 400 MHz
ppm 688 (d J=792 Hz 1 H) 684 (d J=166 Hz 1 H) 676 - 681 (dd J=790 180 Hz 1
H) 597 (s 2 H) 341 - 354 (ddq J=770 670 670 670 650 Hz 1 H) 293 - 302 (dd
J=1400 650 Hz 1 H) 283 (dd J=1400 770 Hz 1 H) 270 (s 3 H) 127 (d J=665 Hz
3 H) Maleic acid 640 (s 2H)
1H NMR MDMA base in CD3OD with TMS
Extracted from MDMA HCl ndash Lot A150B 400 MHz
ppm 669 - 674 (d J=783 Hz 1 H) 667 (d J=137 Hz 1 H) 662 (dd J=780 140 Hz 1
H) 588 (s 2 H) 265 - 276 (m 2 H) 244 (dd J=1530 940 Hz 1 H) 234 (s 3 H) 100
(d J=606 Hz 3 H)
1H NMR MDMA HCl in CD3OD Lot A150B
400 MHz
ppm 680 (d J=160 Hz 1 H) 679 (d J=802 Hz 1 H) 674 (dd J=802 156 Hz 1 H) 593 (s 2 H) 336 -
348 (ddq J=940 650 650 650 530 Hz 1 H) 308 (dd J=1350 528 Hz 1 H) 271 (dd J=1330 940
Hz 1 H) 125 (d J=646 Hz 3 H)
13C NMR MDMA HCl in CD3OD Lot A150B
Optical isomers standards for these compounds were unavailable
No Data Available
FTIR (1 bounce ATR) MDMA phosphate
32 scans resolution 4 cm-1
IR (Vapor Phase) 34-Methylenedioxymethamphetamine Lot A150B
2 mgmL in CH3OH
FT-RAMAN 34-Methylenedioxymethamphetamine Base
Extracted from MDMA HCl Lot A150B 32 scans 4 cm-1
resolution
FT-RAMAN 34-Methylenedioxymethamphetamine HCl
Lot A150B 32 scans 4 cm-1
resolution
19
48
26
09
34
79
36
61
45
675
34
5
60
41
66
74
71
46
77
21
81
27
88
74
10
39
6
10
97
8
11
54
7
12
47
1
12
89
61
33
69
13
60
5
13
98
01
44
19
15
02
5
16
09
41
62
88
27
93
7
29
32
72
96
79
30
37
23
07
03
33
30
5
00
05
10
15
20
25
30
35
40
45
50
55
60
65
70
75
80In
t
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
19
28
25
19
34
08
37
96
41
00
44
79
47
83
53
40
60
51
63
26
71
61
77
55
81
29
88
63
92
73
10
37
9
10
80
1
11
98
1
12
47
9
13
04
51
33
12
13
69
6
14
01
21
44
32
15
07
2
16
09
51
63
15
27
81
1
28
63
62
90
37
29
33
7
29
69
22
99
14
30
58
4
2
4
6
8
10
12
14
16
18
20
22
24
26
Int
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
FT-RAMAN 34-Methylenedioxymethamphetamine Phosphate Lot 2 TDM-275-01
32 scans 4 cm-1
resolution
Mass Spectrometry (EI) 34-Methylenedioxymethamphetamine
10
66
20
68
25
61
34
42
42
41
47
36
53
98
60
38
63
98
71
41
77
72
81
18
83
67
90
70
10
11
8
10
74
91
10
57
12
01
61
22
83
12
55
1
13
53
1
13
99
3
14
42
0
14
91
7
16
07
81
63
02
23
54
027
98
3
29
40
62
96
43
30
40
83
06
97
00
05
10
15
20
25
30
35
40
45
50
55
Int
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
Mass Spectrometry (CI) 34-Methylenedioxymethamphetamine
1H NMR MDMA base in CDCl3 with TMS 400 MHz
Extracted from MDMA HCl ndash Lot A150B
ppm 673 (d J=783 Hz 1 H) 668 (d J=117 Hz 1 H) 663 (dd J=783 117 Hz 1 H) 592 (s 2 H) 267 -
278 (ddq J=720 630 630 630 630 Hz 1 H) 261 (dd J=1350 724 Hz 1 H) 254 (dd J=1330 626
Hz 1 H) 239 (s 3 H) 104 (d J=626 Hz 3 H)
13C NMR MDMA Base
Extracted from MDMA HCl ndash Lot A 150B
1H NMR MDMA Phosphate in D2O with TSP 400 MHz
Lot 2 TDM-275-01
ppm 688 - 692 (d J=800 Hz 1 H) 686 (d J=137 Hz 1 H) 680 (dd J=800 140 Hz 1 H) 598 (s 2 H)
344 - 355 (ddq J=750 670 670 670 650 Hz 1 H) 299 (dd J=1390 650 Hz 1 H) 285 (dd J=1390
760 Hz 1 H) 270 (s 3 H) 128 (d J=665 Hz 3 H)
13C NMR MDMA Phosphate in D2O with TSP Lot 2 TDM-275-01
1H NMR MDMA Phosphate in CD3OD with TMS Lot 2 TDM-275-01
400 MHz
ppm 679 (d J=098 Hz 1 H) 678 (d J=802 Hz 1 H) 673 (dd J=800 120 Hz 1 H)
593 (s 2 H) 329 - 340 (m 1 H) 308 (dd J=1350 509 Hz 1 H) 269 (s 3 H) 267 (dd
J=1330 960 Hz 1 H) 122 (d J=646 Hz 3 H)
1H NMR MDMA HCl Lot A150B
with maleic acid as internal standard in D2O with TSP 400 MHz
ppm 688 (d J=792 Hz 1 H) 684 (d J=166 Hz 1 H) 676 - 681 (dd J=790 180 Hz 1
H) 597 (s 2 H) 341 - 354 (ddq J=770 670 670 670 650 Hz 1 H) 293 - 302 (dd
J=1400 650 Hz 1 H) 283 (dd J=1400 770 Hz 1 H) 270 (s 3 H) 127 (d J=665 Hz
3 H) Maleic acid 640 (s 2H)
1H NMR MDMA base in CD3OD with TMS
Extracted from MDMA HCl ndash Lot A150B 400 MHz
ppm 669 - 674 (d J=783 Hz 1 H) 667 (d J=137 Hz 1 H) 662 (dd J=780 140 Hz 1
H) 588 (s 2 H) 265 - 276 (m 2 H) 244 (dd J=1530 940 Hz 1 H) 234 (s 3 H) 100
(d J=606 Hz 3 H)
1H NMR MDMA HCl in CD3OD Lot A150B
400 MHz
ppm 680 (d J=160 Hz 1 H) 679 (d J=802 Hz 1 H) 674 (dd J=802 156 Hz 1 H) 593 (s 2 H) 336 -
348 (ddq J=940 650 650 650 530 Hz 1 H) 308 (dd J=1350 528 Hz 1 H) 271 (dd J=1330 940
Hz 1 H) 125 (d J=646 Hz 3 H)
13C NMR MDMA HCl in CD3OD Lot A150B
Optical isomers standards for these compounds were unavailable
No Data Available
FT-RAMAN 34-Methylenedioxymethamphetamine Base
Extracted from MDMA HCl Lot A150B 32 scans 4 cm-1
resolution
FT-RAMAN 34-Methylenedioxymethamphetamine HCl
Lot A150B 32 scans 4 cm-1
resolution
19
48
26
09
34
79
36
61
45
675
34
5
60
41
66
74
71
46
77
21
81
27
88
74
10
39
6
10
97
8
11
54
7
12
47
1
12
89
61
33
69
13
60
5
13
98
01
44
19
15
02
5
16
09
41
62
88
27
93
7
29
32
72
96
79
30
37
23
07
03
33
30
5
00
05
10
15
20
25
30
35
40
45
50
55
60
65
70
75
80In
t
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
19
28
25
19
34
08
37
96
41
00
44
79
47
83
53
40
60
51
63
26
71
61
77
55
81
29
88
63
92
73
10
37
9
10
80
1
11
98
1
12
47
9
13
04
51
33
12
13
69
6
14
01
21
44
32
15
07
2
16
09
51
63
15
27
81
1
28
63
62
90
37
29
33
7
29
69
22
99
14
30
58
4
2
4
6
8
10
12
14
16
18
20
22
24
26
Int
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
FT-RAMAN 34-Methylenedioxymethamphetamine Phosphate Lot 2 TDM-275-01
32 scans 4 cm-1
resolution
Mass Spectrometry (EI) 34-Methylenedioxymethamphetamine
10
66
20
68
25
61
34
42
42
41
47
36
53
98
60
38
63
98
71
41
77
72
81
18
83
67
90
70
10
11
8
10
74
91
10
57
12
01
61
22
83
12
55
1
13
53
1
13
99
3
14
42
0
14
91
7
16
07
81
63
02
23
54
027
98
3
29
40
62
96
43
30
40
83
06
97
00
05
10
15
20
25
30
35
40
45
50
55
Int
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
Mass Spectrometry (CI) 34-Methylenedioxymethamphetamine
1H NMR MDMA base in CDCl3 with TMS 400 MHz
Extracted from MDMA HCl ndash Lot A150B
ppm 673 (d J=783 Hz 1 H) 668 (d J=117 Hz 1 H) 663 (dd J=783 117 Hz 1 H) 592 (s 2 H) 267 -
278 (ddq J=720 630 630 630 630 Hz 1 H) 261 (dd J=1350 724 Hz 1 H) 254 (dd J=1330 626
Hz 1 H) 239 (s 3 H) 104 (d J=626 Hz 3 H)
13C NMR MDMA Base
Extracted from MDMA HCl ndash Lot A 150B
1H NMR MDMA Phosphate in D2O with TSP 400 MHz
Lot 2 TDM-275-01
ppm 688 - 692 (d J=800 Hz 1 H) 686 (d J=137 Hz 1 H) 680 (dd J=800 140 Hz 1 H) 598 (s 2 H)
344 - 355 (ddq J=750 670 670 670 650 Hz 1 H) 299 (dd J=1390 650 Hz 1 H) 285 (dd J=1390
760 Hz 1 H) 270 (s 3 H) 128 (d J=665 Hz 3 H)
13C NMR MDMA Phosphate in D2O with TSP Lot 2 TDM-275-01
1H NMR MDMA Phosphate in CD3OD with TMS Lot 2 TDM-275-01
400 MHz
ppm 679 (d J=098 Hz 1 H) 678 (d J=802 Hz 1 H) 673 (dd J=800 120 Hz 1 H)
593 (s 2 H) 329 - 340 (m 1 H) 308 (dd J=1350 509 Hz 1 H) 269 (s 3 H) 267 (dd
J=1330 960 Hz 1 H) 122 (d J=646 Hz 3 H)
1H NMR MDMA HCl Lot A150B
with maleic acid as internal standard in D2O with TSP 400 MHz
ppm 688 (d J=792 Hz 1 H) 684 (d J=166 Hz 1 H) 676 - 681 (dd J=790 180 Hz 1
H) 597 (s 2 H) 341 - 354 (ddq J=770 670 670 670 650 Hz 1 H) 293 - 302 (dd
J=1400 650 Hz 1 H) 283 (dd J=1400 770 Hz 1 H) 270 (s 3 H) 127 (d J=665 Hz
3 H) Maleic acid 640 (s 2H)
1H NMR MDMA base in CD3OD with TMS
Extracted from MDMA HCl ndash Lot A150B 400 MHz
ppm 669 - 674 (d J=783 Hz 1 H) 667 (d J=137 Hz 1 H) 662 (dd J=780 140 Hz 1
H) 588 (s 2 H) 265 - 276 (m 2 H) 244 (dd J=1530 940 Hz 1 H) 234 (s 3 H) 100
(d J=606 Hz 3 H)
1H NMR MDMA HCl in CD3OD Lot A150B
400 MHz
ppm 680 (d J=160 Hz 1 H) 679 (d J=802 Hz 1 H) 674 (dd J=802 156 Hz 1 H) 593 (s 2 H) 336 -
348 (ddq J=940 650 650 650 530 Hz 1 H) 308 (dd J=1350 528 Hz 1 H) 271 (dd J=1330 940
Hz 1 H) 125 (d J=646 Hz 3 H)
13C NMR MDMA HCl in CD3OD Lot A150B
Optical isomers standards for these compounds were unavailable
No Data Available
FT-RAMAN 34-Methylenedioxymethamphetamine Phosphate Lot 2 TDM-275-01
32 scans 4 cm-1
resolution
Mass Spectrometry (EI) 34-Methylenedioxymethamphetamine
10
66
20
68
25
61
34
42
42
41
47
36
53
98
60
38
63
98
71
41
77
72
81
18
83
67
90
70
10
11
8
10
74
91
10
57
12
01
61
22
83
12
55
1
13
53
1
13
99
3
14
42
0
14
91
7
16
07
81
63
02
23
54
027
98
3
29
40
62
96
43
30
40
83
06
97
00
05
10
15
20
25
30
35
40
45
50
55
Int
500 1000 1500 2000 2500 3000 3500
Raman shift (cm-1)
Mass Spectrometry (CI) 34-Methylenedioxymethamphetamine
1H NMR MDMA base in CDCl3 with TMS 400 MHz
Extracted from MDMA HCl ndash Lot A150B
ppm 673 (d J=783 Hz 1 H) 668 (d J=117 Hz 1 H) 663 (dd J=783 117 Hz 1 H) 592 (s 2 H) 267 -
278 (ddq J=720 630 630 630 630 Hz 1 H) 261 (dd J=1350 724 Hz 1 H) 254 (dd J=1330 626
Hz 1 H) 239 (s 3 H) 104 (d J=626 Hz 3 H)
13C NMR MDMA Base
Extracted from MDMA HCl ndash Lot A 150B
1H NMR MDMA Phosphate in D2O with TSP 400 MHz
Lot 2 TDM-275-01
ppm 688 - 692 (d J=800 Hz 1 H) 686 (d J=137 Hz 1 H) 680 (dd J=800 140 Hz 1 H) 598 (s 2 H)
344 - 355 (ddq J=750 670 670 670 650 Hz 1 H) 299 (dd J=1390 650 Hz 1 H) 285 (dd J=1390
760 Hz 1 H) 270 (s 3 H) 128 (d J=665 Hz 3 H)
13C NMR MDMA Phosphate in D2O with TSP Lot 2 TDM-275-01
1H NMR MDMA Phosphate in CD3OD with TMS Lot 2 TDM-275-01
400 MHz
ppm 679 (d J=098 Hz 1 H) 678 (d J=802 Hz 1 H) 673 (dd J=800 120 Hz 1 H)
593 (s 2 H) 329 - 340 (m 1 H) 308 (dd J=1350 509 Hz 1 H) 269 (s 3 H) 267 (dd
J=1330 960 Hz 1 H) 122 (d J=646 Hz 3 H)
1H NMR MDMA HCl Lot A150B
with maleic acid as internal standard in D2O with TSP 400 MHz
ppm 688 (d J=792 Hz 1 H) 684 (d J=166 Hz 1 H) 676 - 681 (dd J=790 180 Hz 1
H) 597 (s 2 H) 341 - 354 (ddq J=770 670 670 670 650 Hz 1 H) 293 - 302 (dd
J=1400 650 Hz 1 H) 283 (dd J=1400 770 Hz 1 H) 270 (s 3 H) 127 (d J=665 Hz
3 H) Maleic acid 640 (s 2H)
1H NMR MDMA base in CD3OD with TMS
Extracted from MDMA HCl ndash Lot A150B 400 MHz
ppm 669 - 674 (d J=783 Hz 1 H) 667 (d J=137 Hz 1 H) 662 (dd J=780 140 Hz 1
H) 588 (s 2 H) 265 - 276 (m 2 H) 244 (dd J=1530 940 Hz 1 H) 234 (s 3 H) 100
(d J=606 Hz 3 H)
1H NMR MDMA HCl in CD3OD Lot A150B
400 MHz
ppm 680 (d J=160 Hz 1 H) 679 (d J=802 Hz 1 H) 674 (dd J=802 156 Hz 1 H) 593 (s 2 H) 336 -
348 (ddq J=940 650 650 650 530 Hz 1 H) 308 (dd J=1350 528 Hz 1 H) 271 (dd J=1330 940
Hz 1 H) 125 (d J=646 Hz 3 H)
13C NMR MDMA HCl in CD3OD Lot A150B
Optical isomers standards for these compounds were unavailable
No Data Available
Mass Spectrometry (CI) 34-Methylenedioxymethamphetamine
1H NMR MDMA base in CDCl3 with TMS 400 MHz
Extracted from MDMA HCl ndash Lot A150B
ppm 673 (d J=783 Hz 1 H) 668 (d J=117 Hz 1 H) 663 (dd J=783 117 Hz 1 H) 592 (s 2 H) 267 -
278 (ddq J=720 630 630 630 630 Hz 1 H) 261 (dd J=1350 724 Hz 1 H) 254 (dd J=1330 626
Hz 1 H) 239 (s 3 H) 104 (d J=626 Hz 3 H)
13C NMR MDMA Base
Extracted from MDMA HCl ndash Lot A 150B
1H NMR MDMA Phosphate in D2O with TSP 400 MHz
Lot 2 TDM-275-01
ppm 688 - 692 (d J=800 Hz 1 H) 686 (d J=137 Hz 1 H) 680 (dd J=800 140 Hz 1 H) 598 (s 2 H)
344 - 355 (ddq J=750 670 670 670 650 Hz 1 H) 299 (dd J=1390 650 Hz 1 H) 285 (dd J=1390
760 Hz 1 H) 270 (s 3 H) 128 (d J=665 Hz 3 H)
13C NMR MDMA Phosphate in D2O with TSP Lot 2 TDM-275-01
1H NMR MDMA Phosphate in CD3OD with TMS Lot 2 TDM-275-01
400 MHz
ppm 679 (d J=098 Hz 1 H) 678 (d J=802 Hz 1 H) 673 (dd J=800 120 Hz 1 H)
593 (s 2 H) 329 - 340 (m 1 H) 308 (dd J=1350 509 Hz 1 H) 269 (s 3 H) 267 (dd
J=1330 960 Hz 1 H) 122 (d J=646 Hz 3 H)
1H NMR MDMA HCl Lot A150B
with maleic acid as internal standard in D2O with TSP 400 MHz
ppm 688 (d J=792 Hz 1 H) 684 (d J=166 Hz 1 H) 676 - 681 (dd J=790 180 Hz 1
H) 597 (s 2 H) 341 - 354 (ddq J=770 670 670 670 650 Hz 1 H) 293 - 302 (dd
J=1400 650 Hz 1 H) 283 (dd J=1400 770 Hz 1 H) 270 (s 3 H) 127 (d J=665 Hz
3 H) Maleic acid 640 (s 2H)
1H NMR MDMA base in CD3OD with TMS
Extracted from MDMA HCl ndash Lot A150B 400 MHz
ppm 669 - 674 (d J=783 Hz 1 H) 667 (d J=137 Hz 1 H) 662 (dd J=780 140 Hz 1
H) 588 (s 2 H) 265 - 276 (m 2 H) 244 (dd J=1530 940 Hz 1 H) 234 (s 3 H) 100
(d J=606 Hz 3 H)
1H NMR MDMA HCl in CD3OD Lot A150B
400 MHz
ppm 680 (d J=160 Hz 1 H) 679 (d J=802 Hz 1 H) 674 (dd J=802 156 Hz 1 H) 593 (s 2 H) 336 -
348 (ddq J=940 650 650 650 530 Hz 1 H) 308 (dd J=1350 528 Hz 1 H) 271 (dd J=1330 940
Hz 1 H) 125 (d J=646 Hz 3 H)
13C NMR MDMA HCl in CD3OD Lot A150B
Optical isomers standards for these compounds were unavailable
No Data Available
13C NMR MDMA Base
Extracted from MDMA HCl ndash Lot A 150B
1H NMR MDMA Phosphate in D2O with TSP 400 MHz
Lot 2 TDM-275-01
ppm 688 - 692 (d J=800 Hz 1 H) 686 (d J=137 Hz 1 H) 680 (dd J=800 140 Hz 1 H) 598 (s 2 H)
344 - 355 (ddq J=750 670 670 670 650 Hz 1 H) 299 (dd J=1390 650 Hz 1 H) 285 (dd J=1390
760 Hz 1 H) 270 (s 3 H) 128 (d J=665 Hz 3 H)
13C NMR MDMA Phosphate in D2O with TSP Lot 2 TDM-275-01
1H NMR MDMA Phosphate in CD3OD with TMS Lot 2 TDM-275-01
400 MHz
ppm 679 (d J=098 Hz 1 H) 678 (d J=802 Hz 1 H) 673 (dd J=800 120 Hz 1 H)
593 (s 2 H) 329 - 340 (m 1 H) 308 (dd J=1350 509 Hz 1 H) 269 (s 3 H) 267 (dd
J=1330 960 Hz 1 H) 122 (d J=646 Hz 3 H)
1H NMR MDMA HCl Lot A150B
with maleic acid as internal standard in D2O with TSP 400 MHz
ppm 688 (d J=792 Hz 1 H) 684 (d J=166 Hz 1 H) 676 - 681 (dd J=790 180 Hz 1
H) 597 (s 2 H) 341 - 354 (ddq J=770 670 670 670 650 Hz 1 H) 293 - 302 (dd
J=1400 650 Hz 1 H) 283 (dd J=1400 770 Hz 1 H) 270 (s 3 H) 127 (d J=665 Hz
3 H) Maleic acid 640 (s 2H)
1H NMR MDMA base in CD3OD with TMS
Extracted from MDMA HCl ndash Lot A150B 400 MHz
ppm 669 - 674 (d J=783 Hz 1 H) 667 (d J=137 Hz 1 H) 662 (dd J=780 140 Hz 1
H) 588 (s 2 H) 265 - 276 (m 2 H) 244 (dd J=1530 940 Hz 1 H) 234 (s 3 H) 100
(d J=606 Hz 3 H)
1H NMR MDMA HCl in CD3OD Lot A150B
400 MHz
ppm 680 (d J=160 Hz 1 H) 679 (d J=802 Hz 1 H) 674 (dd J=802 156 Hz 1 H) 593 (s 2 H) 336 -
348 (ddq J=940 650 650 650 530 Hz 1 H) 308 (dd J=1350 528 Hz 1 H) 271 (dd J=1330 940
Hz 1 H) 125 (d J=646 Hz 3 H)
13C NMR MDMA HCl in CD3OD Lot A150B
Optical isomers standards for these compounds were unavailable
No Data Available
1H NMR MDMA Phosphate in D2O with TSP 400 MHz
Lot 2 TDM-275-01
ppm 688 - 692 (d J=800 Hz 1 H) 686 (d J=137 Hz 1 H) 680 (dd J=800 140 Hz 1 H) 598 (s 2 H)
344 - 355 (ddq J=750 670 670 670 650 Hz 1 H) 299 (dd J=1390 650 Hz 1 H) 285 (dd J=1390
760 Hz 1 H) 270 (s 3 H) 128 (d J=665 Hz 3 H)
13C NMR MDMA Phosphate in D2O with TSP Lot 2 TDM-275-01
1H NMR MDMA Phosphate in CD3OD with TMS Lot 2 TDM-275-01
400 MHz
ppm 679 (d J=098 Hz 1 H) 678 (d J=802 Hz 1 H) 673 (dd J=800 120 Hz 1 H)
593 (s 2 H) 329 - 340 (m 1 H) 308 (dd J=1350 509 Hz 1 H) 269 (s 3 H) 267 (dd
J=1330 960 Hz 1 H) 122 (d J=646 Hz 3 H)
1H NMR MDMA HCl Lot A150B
with maleic acid as internal standard in D2O with TSP 400 MHz
ppm 688 (d J=792 Hz 1 H) 684 (d J=166 Hz 1 H) 676 - 681 (dd J=790 180 Hz 1
H) 597 (s 2 H) 341 - 354 (ddq J=770 670 670 670 650 Hz 1 H) 293 - 302 (dd
J=1400 650 Hz 1 H) 283 (dd J=1400 770 Hz 1 H) 270 (s 3 H) 127 (d J=665 Hz
3 H) Maleic acid 640 (s 2H)
1H NMR MDMA base in CD3OD with TMS
Extracted from MDMA HCl ndash Lot A150B 400 MHz
ppm 669 - 674 (d J=783 Hz 1 H) 667 (d J=137 Hz 1 H) 662 (dd J=780 140 Hz 1
H) 588 (s 2 H) 265 - 276 (m 2 H) 244 (dd J=1530 940 Hz 1 H) 234 (s 3 H) 100
(d J=606 Hz 3 H)
1H NMR MDMA HCl in CD3OD Lot A150B
400 MHz
ppm 680 (d J=160 Hz 1 H) 679 (d J=802 Hz 1 H) 674 (dd J=802 156 Hz 1 H) 593 (s 2 H) 336 -
348 (ddq J=940 650 650 650 530 Hz 1 H) 308 (dd J=1350 528 Hz 1 H) 271 (dd J=1330 940
Hz 1 H) 125 (d J=646 Hz 3 H)
13C NMR MDMA HCl in CD3OD Lot A150B
Optical isomers standards for these compounds were unavailable
No Data Available
13C NMR MDMA Phosphate in D2O with TSP Lot 2 TDM-275-01
1H NMR MDMA Phosphate in CD3OD with TMS Lot 2 TDM-275-01
400 MHz
ppm 679 (d J=098 Hz 1 H) 678 (d J=802 Hz 1 H) 673 (dd J=800 120 Hz 1 H)
593 (s 2 H) 329 - 340 (m 1 H) 308 (dd J=1350 509 Hz 1 H) 269 (s 3 H) 267 (dd
J=1330 960 Hz 1 H) 122 (d J=646 Hz 3 H)
1H NMR MDMA HCl Lot A150B
with maleic acid as internal standard in D2O with TSP 400 MHz
ppm 688 (d J=792 Hz 1 H) 684 (d J=166 Hz 1 H) 676 - 681 (dd J=790 180 Hz 1
H) 597 (s 2 H) 341 - 354 (ddq J=770 670 670 670 650 Hz 1 H) 293 - 302 (dd
J=1400 650 Hz 1 H) 283 (dd J=1400 770 Hz 1 H) 270 (s 3 H) 127 (d J=665 Hz
3 H) Maleic acid 640 (s 2H)
1H NMR MDMA base in CD3OD with TMS
Extracted from MDMA HCl ndash Lot A150B 400 MHz
ppm 669 - 674 (d J=783 Hz 1 H) 667 (d J=137 Hz 1 H) 662 (dd J=780 140 Hz 1
H) 588 (s 2 H) 265 - 276 (m 2 H) 244 (dd J=1530 940 Hz 1 H) 234 (s 3 H) 100
(d J=606 Hz 3 H)
1H NMR MDMA HCl in CD3OD Lot A150B
400 MHz
ppm 680 (d J=160 Hz 1 H) 679 (d J=802 Hz 1 H) 674 (dd J=802 156 Hz 1 H) 593 (s 2 H) 336 -
348 (ddq J=940 650 650 650 530 Hz 1 H) 308 (dd J=1350 528 Hz 1 H) 271 (dd J=1330 940
Hz 1 H) 125 (d J=646 Hz 3 H)
13C NMR MDMA HCl in CD3OD Lot A150B
Optical isomers standards for these compounds were unavailable
No Data Available
1H NMR MDMA HCl Lot A150B
with maleic acid as internal standard in D2O with TSP 400 MHz
ppm 688 (d J=792 Hz 1 H) 684 (d J=166 Hz 1 H) 676 - 681 (dd J=790 180 Hz 1
H) 597 (s 2 H) 341 - 354 (ddq J=770 670 670 670 650 Hz 1 H) 293 - 302 (dd
J=1400 650 Hz 1 H) 283 (dd J=1400 770 Hz 1 H) 270 (s 3 H) 127 (d J=665 Hz
3 H) Maleic acid 640 (s 2H)
1H NMR MDMA base in CD3OD with TMS
Extracted from MDMA HCl ndash Lot A150B 400 MHz
ppm 669 - 674 (d J=783 Hz 1 H) 667 (d J=137 Hz 1 H) 662 (dd J=780 140 Hz 1
H) 588 (s 2 H) 265 - 276 (m 2 H) 244 (dd J=1530 940 Hz 1 H) 234 (s 3 H) 100
(d J=606 Hz 3 H)
1H NMR MDMA HCl in CD3OD Lot A150B
400 MHz
ppm 680 (d J=160 Hz 1 H) 679 (d J=802 Hz 1 H) 674 (dd J=802 156 Hz 1 H) 593 (s 2 H) 336 -
348 (ddq J=940 650 650 650 530 Hz 1 H) 308 (dd J=1350 528 Hz 1 H) 271 (dd J=1330 940
Hz 1 H) 125 (d J=646 Hz 3 H)
13C NMR MDMA HCl in CD3OD Lot A150B
Optical isomers standards for these compounds were unavailable
No Data Available
1H NMR MDMA HCl in CD3OD Lot A150B
400 MHz
ppm 680 (d J=160 Hz 1 H) 679 (d J=802 Hz 1 H) 674 (dd J=802 156 Hz 1 H) 593 (s 2 H) 336 -
348 (ddq J=940 650 650 650 530 Hz 1 H) 308 (dd J=1350 528 Hz 1 H) 271 (dd J=1330 940
Hz 1 H) 125 (d J=646 Hz 3 H)
13C NMR MDMA HCl in CD3OD Lot A150B
Optical isomers standards for these compounds were unavailable
No Data Available
13C NMR MDMA HCl in CD3OD Lot A150B
Optical isomers standards for these compounds were unavailable
No Data Available