Cannabinoids structures march 31 2013
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Transcript of Cannabinoids structures march 31 2013
About Synthetic CannabinoidsSynthetic cannabinoids are functionally similar to Δ9-tetrahydrocannabinol (THC), the active principle of cannabis. Like THC, they bind to the same cannabinoid receptors in the brain and other organs as the endogenous ligand anandamide. In late 2008, several cannabinoids were detected in herbal smoking mixtures or incense. They do not contain tobacco or cannabis but when smoked, produce effects similar to those of cannabis (EMCDDA, 2013).
The synthetic cannabinoids fall into seven major structural groups:
Naphthoylindoles (e.g. JWH-018, JWH-073 and JWH-398).Naphthylmethylindoles.Naphthoylpyrroles.Naphthylmethylindenes.Phenylacetylindoles (i.e. benzoylindoles, e.g. JWH-250).Cyclohexylphenols (e.g. CP 47,497 and homologues of CP 47,497).Classical cannabinoids (e.g. HU-210).
K2
Genie Yucatan Fire
Skunk
Sence
SmokeChillXHighdi’s Almdröhner
Earth Impact
Gorillaz
Galaxy Gold Space Truckin
Solar FlareMoon Rocks
Aroma
Blue Lotus
Scope
Sky
JWH-167 (Phenyl)JWH-203 (Phenyl)
JWH-250 (Phenyl) JWH-251 (Phenyl)JWH-320 (Phenyl)RCS-8 (Phenyl)
Naphthoylindoles
JWH-007 (Naph)JWH-015 (Naph)JWH-018 (Naph)JWH-019 (Naph)JWH-081 (Naph)JWH-098 (Naph)JWH-116 (Naph)MAM-2201AM-2201 (Naph)AM-1220AM-1235AM-2232
AM-1248 (Adam)AB-001 (Adam)
CP 47, 497 (non-classical) CP 55,244 (non-classical)CP 55,940 (non-classical)HU-308 (non-classical)
AM-2233 (benz)RCS-4 (Benz)AM-694 (benz)AM-630 (benzoil)
AM-630 AM-679 AM-694
AM-1241 AM-2233 RCS-4
ResearchInverse Agonist for CB2
Ki= 32.1nM at CB2
165x fold selectivity over CB1
ResearchAgonist for CB1 and CB2
Ki = 13.5nM at CB1
Ki = 49.5nM at CB2.
Designer DrugMap CB1 RreceptorSelective Agonist for CB1
Ki = ? 13.5nM at CB1
Peripheral CB receptorKi= 2.1nM at CB12
100 fold selectivity over CB1
Potent agonist Ki = 1.8nM at CB1
Ki = 2.2nM at CB2
JWH 018 analog Found in ‘herbal incense’ products
Naphthoylindoles
AM-1220 AM-1221 AM-1235
AM-2201AM-2232 JWH-007
ResearchAgonist for CB1
Ki = 3.88 nM CB1
Ki = 73.4 nM CB2
ResearchAgonist for CB2
Ki = 52.4 nM CB1
Ki = 0.28 nM CB2
ResearchAgonist for CB1
Ki = 1.50 nM CB1
Ki = 20.4 nM CB2
ResearchAgonist Ki = 1.0 nM CB1
Ki = 2.6 nM CB2
ResearchAgonist Ki = 0.28 nM CB1
Ki = 1.48 nM CB2
‘Herbal Synthetic’Agonist Ki = 9.0 nM CB1
Ki = 2.9 nM CB2
JWH-015 JWH-018 JWH-019
JWH-073 JWH-081 JWH-098
ResearchAgonist for CB2
Ki = 388 nM CB1
Ki = 13.9 nM CB2
Synthetic (herbal incense) Full Agonist Ki = 9.00 nM CB1
Ki = 2.94 nM CB2
Synthetic (herbal incense) Full Agonist Ki = 9.80 nM CB1
Ki = 5.60 nM CB2
Synthetic analgesic Full Agonist Ki = 8.9 nM CB1
Ki = 38 nM CB2
Synthetic analgesic Full Agonist Ki = 1.20 nM CB1
Ki = 12.4 nM CB2
Research Full Agonist Ki = 4.50 nM CB1
Ki = 1.88 nM CB2
JWH-116
JWH-149
JWH-193 JWH-198 JWH-200
Research Full Agonist Ki = 52 nM CB1
ResearchAgonist for CB2
Ki = 5.0 nM CB1
Ki = 0.73 nM CB2
ResearchAgonist for CB1
Ki = 10 nM CB1
ResearchAgonist for CB1
Ki = 6 nM CB1
ResearchAnalgesicAgonist for CB1
IC50 = 7.8 - 42 nM
JWH-210 JWH-398 JWH-424
MAM-2201
ResearchAgonist Ki = 0.46 nM CB1
Ki = 0.69 nM CB2
Found in ‘Herbal Incense’ AnalgesicAgonist Ki = 2.3 nM CB1
Ki = 2.8 nM CB2
ResearchAgonist Ki = 20.9 nM CB1
Ki = 5.40 nM CB2
ResearchAgonist Ki = 1.0 nM CB1
Ki = 2.6 nM CB2
CP 47,497 (cannabicyclohexanol) CP 55,940 HU-308
Agonist Ki = 2.2 nM CB1
AnalgesicMotor depresantAnticonvulsants
ResearchAgonist Ki = 0.58 nM CB1
Ki = 0.69 nM CB2
ResearchAgonist Ki = 10 uM CB1
Ki = 20 nM CB2
AgonistPotent analgesicFound in Spice Gold
Phenylacetylindoles
JWH-167 JWH-203 JWH-250
JWH 251
JWH-320
RCS-8
ResearchAgonist Ki = 90 nM CB1
Ki = 159 nM CB2
ResearchAgonist Ki = 8.0 nM CB1
Ki = 7.0 nM CB2
ResearchAgonist Ki = 11.0 nM CB1
Ki = 33.0 nM CB2
Synthetic Herbal