Cannabinoids
These substances are active in single-digit milligram to sub-milligram doses, so vendors often distribute them by measuring doses, dissolving them in Acetone and spraying them on to various inactive plant matter such as Damiana plant to be sold as “Incense” or “Potpourri.” Desired by the public for several reasons: When first released, most could not be detected by standard drug screening tests. Per dose, these compounds have historically been significantly cheaper than marijuana. For a period of a couple years, the JWH series of cannabinoids could be easily perchased at gas stations. New laws over the past years have made the sale of “incense” coated in these drugs more blatantly illegal.
A. JWH series - named after John W. Huffman, the chemist who discovered them. He has sense attempted to distance himself from these chemicals, expressing significant regret during rare interviews with journalists.
1. Napthoylindoles
a) JWH-007 – Illegal in the USA and Europe.
b) JWH-018 (AM-678, (1-pentyl-3-(1-naphthoyl)indole) -detectable
with urine testing. illegal in the USA.
c) JWH-019 - detectable with urine testing. Illegal.
d) JWH-073 - detectable with urine testing. Illegal.
e) JWH-081 - detectable with urine
testing. Illegal.
(1) JWH-081-N-(cyclohexylmethyl) - DEA microgram journal
confirms this one’s presence in “incense” products sold in the
USA as of 2013.
f) JWH-098 - illegal in Russia, Sweden, and the UK.
g) JWH-122 -detectable with urine testing. Illegal.
h) JWH-182 – Illegal. Did not appear to be particularly desired for recreational use.
2. Phenylacetylindoles
a) JWH-203 (1-Pentyl-3-(2-chlorophenylacetyl) indole)- Illegal.
b) JWH-249 – Illegal.
c) JWH-250 (1-Pentyl-3-(2-methoxyphenylacetyl) indole) - Illegal.
d) JWH-251 – Illegal.
3. 4-alkyl substitutions
a) JWH-210 – illegal.
4. Aminoalkylindoles
a) JWH-200 (WIN-55,225, (1-(2-morpholin-4-ylethyl)indol-3-yl)-
naphthalen-1-ylmethanone) - Illegal.
b) Pravadoline (WIN-48,098, (4-methoxyphenyl)-[2-methyl-1-(2- morpholin-4-ylethyl)indol-3-yl]methanone)
B. AM series - discovered by the chemist Alexandros Makriyannis. Appear to have more side effects compared to the JWH series. Only started appearing for sale after laws banning the JWH compounds were passed by several state legislatures.
1. AM-630 (6-iodopravadoline) - weak partial agonist for CB1, inverse
agonist for CB2.
2. AM-679 (1-pentyl-3-(2-iodobenzoyl)indole)
3. AM-694 (1-(5-fluoropentyl)-3-(2-iodobenzoyl)indole) - Illegal.
4. AM-1220 ((R)-(1-((1-methylpiperidin-2-yl)methyl)-1H-indol-3-yl)
(naphthalen-1-yl)methanone)
5. AM-1221 (1-[(N-methylpiperidin-2-yl)methyl]-2-methyl-3-
(naphthalen-1-oyl)-6-nitroindole)
6. AM-1241 (1-(methylpiperidin-2-ylmethyl)-3-(2-iodo-5-
nitrobenzoyl)indole)
7. AM-1248
8. AM-2201 - linked to acute kidney injury. Detectable with urine
testing. Illegal.
a) MAM-2201 (5F-JWH-122, [1-(5-fluoropentyl)-1H-indol-3-yl]-(4-
methyl-1-naphthalenyl)-methanone) - 4-methyl analog of
AM-2201.
9. AM-2232 (1-(4-cyanobutyl)-3-(naphthalen-1-oyl)indole)
10. AM-2233 (1-[(N-methylpiperidin-2-yl)methyl]-3-(2- iodobenzoyl)indole) – illegal.
C. Miscellaneous cannabinoids
1. UR-144 - Detectable with urine testing. Illegal.
a) 5F-UR-144 (XLR-11, (1-(5-fluoropentyl)-1H-indol-3-yl)(2,2,3,3-
tetramethylcyclopropyl)methanone) - associated with acute kidney injury. Detectable with urine testing. Illegal. (1)FAB-144 (1-(5-Fluoro-pentyl)-1H-indole-3-carboxylic acid (1-carbamoyl-2-methyl-propyl)-amide) - analogue of 5F-UR-144.
2. APICA (2-NE1, SDB-001, N-(1-adamantyl)-1-pentyl-1H-indole-3-
carboxamide) - full agonist at receptors CB1 and CB2.
a) STS-135 (5F-APICA, (5-fluoro)-N-(adamantan-1-yl)-1-pentyl-1H-indole-3-carboxamide) – terminally fluorinated analog of APICA.
b) ADBICA (N-(1-amino-3,3-dimethyl-1-oxobutan-2-yl)-1-pentyl-1H-indole-3-carboxamide) - Found in synthetic cannabis blends in Japan in 2013.
3. APINACA (AKB-48, N-(1-adamantyl)-1-pentyl-1H-indazole-3-carboxamide) - Illegal.
a) 5F-APINACA (5F-AKB-48, N-((3s,5s,7s)-adamantan-1-yl)-1-(5-fluoropentyl)-1H-indazole-3-carboxamide)
4. AB-PINACA (N-[(1S)-1-(aminocarbonyl)-2-methylpropyl]-1-pentyl-1H-indazole-3-carboxamide)
a) 5F-AB-PINACA ((S)-N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-(5-fluoropentyl)-1H-indazole-3-carboxamide)
b) ADB-PINACA (N-(1-amino-3,3-dimethyl-1-oxobutan-2-yl)-1-pentyl-1H-indazole-3-carboxamide) - Illegal.
c) 5F-AMB ((R)-methyl-2-(1-(5-fluoropentyl)-1H-indazole-3-carboxamido)-3-methylbutanoate) - analogue of AB-PINACA
5. AB-CHMINACA ((R)-N-(1-amino-3-methyl-1-oxobutan-2-yl)-1- (cyclohexylmethyl)-1H-indazole-3-carboxamide)
6. AB-FUBINACA (N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-(4- fluorobenzyl)-1H-indazole-3-carboxamide) - Illegal.
a) ADB-FUBINACA (N-(1-Amino-3,3-dimethyl-1-oxobutan-2-yl)-1-(4-fluorobenzyl)-1H-indazole-3-carboxamide) - Found in synthetic cannabis blends in Japan in 2013.
7. QUPIC (PB-22, 8-quinolinyl ester-1-pentyl-1H-indole-3-carboxylic acid) - detectable with urine testing. Found in some synthetic cannabis blends tested in Japan in 2013.
a) 5F-QUPIC (5F-PB-22, (5-fluoro)-8-quinolinyl ester-1-(pentyl)-1H-indole-3-carboxylic acid) - Illegal.
b) FUB-QUPIC (FUB-PB-22, quinolin-8-yl-1-(4-fluorobenzyl)-1H-indole-3-carboxylate) - analog of PB-22 with the pentyl side chain replaced by a 4-fluorobenzyl group and the 8-quinolinol replaced by a naphthalene group.
8. QUCHIC (BB-22, 8-quinolinyl ester-1-(cyclohexylmethyl)-1H- indole-3-carboxylic acid) – also found in synthetic cannabis blends in Japan in 2013.
9. MEPIRAPIM (4-methylpiperazin-1-yl)(1-pentyl-1H-indol-3- yl)methanone
10.MN-18 (1-pentyl-N-(naphthalen-1-yl)-1H-indazole-3-carboxamide) a) 5F-MN-18 (1-(5-fluoropentyl)-N-(naphthalen-1-yl)-1H-indazole-3-carboxamide)
11. MN-24 (NNE1, AM-6527, N-1-naphthalenyl-1-pentyl-1H-indole-3-
carboxamide)
a) 5F-MN-24 (5F-NNE1, 1-(5-fluoropentyl)-N-(naphthalen-1-
yl)-1H-indole-3-carboxamide)
b) 5-C-NNEI (5-chloro-NNEI)
c) NNEI indazole analog ([N-(Naphthalen-1-yl)-1-pentyl-1H-
indazole-3-carboxamide])
12. MN-25 (UR-12, 7-methoxy-1-(2-morpholinoethyl)-N-((1S,4R)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl)-1H-indole-3-carboxamide (N-[(S)-fenchyl]-1-[2-(morpholin-4-yl)ethyl]-7- methoxyindole-3-carboxamide)
13. 5F-SDB-005 (1-(5-Fluoro-pentyl)-1H-indazole-3-carboxylic acid naphthalen-1-yl ester)
14. SDB-006 (N-benzyl-1-pentyl-1H-indole-3-carboxamide)
a) 5F-SDB-006 (5F analogue of N-benzyl-1-pentyl-1H-indole-3-
carboxamide)
15. RCS-4 (SR-19, 1-pentyl-3-(4-methoxybenzoyl)indole) - Illegal.
16. RCS-8 (SR-18, BTM-8, 1-(2-cyclohexylethyl)-3-(2- methoxyphenylacetyl)indole) - Illegal.
17. JTE-907 (N-(benzo[1,3]dioxol-5-ylmethyl)-7-methoxy-2-oxo-8- pentyloxy-1,2-dihydroquinoline-3-carboxamide) - this is a selective CB2 inverse agonist.
18. Org-28611 (SCH-900,111 , [1-(cyclohexylmethyl)-7- methoxyindol-3-yl]-[(3S)-3,4-dimethylpiperazin-1-yl]methanone)
19. JTE 7-31 (2-[2-(4-hydroxyphenyl)ethyl]-5-methoxy-4- (pentylamino)-2,3-dihydro-1H-isoindol-1-one) - discovered by Japan Tobacco.
20. A-796,260 (1-(2-morpholin-4-ylethyl)-1H-indol-3-yl]-(2,2,3,3- tetramethylcyclopropyl)methanone) -
21. A-834,735 (1-(tetrahydropyran-4-ylmethyl)-1H-indol-3-yl]- (2,2,3,3-tetramethylcyclopropyl)methanone)
22. A-836,339 (N-[3-(2-methoxyethyl)-4,5-dimethyl-1,3-thiazol-2- ylidene]-2,2,3,3-tetramethylcyclopropane-1-carboxamide)
23. HU-210 (1,1-dimethylheptyl-11-hydroxytetrahydrocannabinol) - discovered by Hebrew University. 100-800x the potency of THC.
24. CP-47,497 (cannabicyclohexanol, 2-[(1R,3S)-3- hydroxycyclohexyl]- 5-(2-methyloctan-2-yl)phenol) - Illegal.
25. CP-55,940
26. AB-001 (1-pentyl-3-(1-adamantoyl)indole)
27. AB-002
28. AB-005 ([1-[(1-methyl-2-piperidinyl)methyl]-1H-indol-3-yl](2,2,3,3-tetramethylcyclopropyl)-methanone)
29. CB-13 (SAB-378, naphthalen-1-yl-(4-pentyloxynaphthalen-1-yl)methanone)
30. MDA-19 ((2Z)-2-(1-hexyl-1,2-dihydro-2-oxo-3H-indol-3-ylidene)hydrazide, benzoic acid)
31. EG-018 (naphthalen-1-yl(9-pentyl-9H-carbazol-3-yl)methanone)
D. THJ series - indazole analogues of indole cannabinoids. Basically, these are analogs of the JWH series.
1. THJ (1-pentyl-N-(quinolin-8-yl)-1H-indazole-3-carboxamide)
2. THJ-018 (1-naphthalenyl(1-pentyl-1H-indazol-3-yl)-methanone)
3. THJ-2201 (1-[(5-fluoropentyl)-1H-indazol-3-yl](naphthalen-1-
yl)methanone)
E. Endocannabinoid reuptake inhibitors – these drugs, instead of directly agonizing cannabinoid receptors, increase concentrations of cannabinoids already present in the body, such as anandamide. Relatively new on the synthetic marijuana scene.
1. URB-597 ([3-(3-carbamoylphenyl)phenyl] N-cyclohexylcarbamate)
2. LY-2,183,240 (N,N-dimethyl-5-[(4-biphenyl)methyl]tetrazole-1-
carboxamide)
3. LY-2,183,240 (N,N-dimethyl-4-[(4-biphenyl)methyl]tetrazole-1-
carboxamide)
4. URB-754 (6-methyl-2-[(4-methylphenyl)amino]-4H-3,1-
benzoxazin-4-one)