JWH-081 is an analgesic chemical from the naphthoylindole family, which acts as a cannabinoid agonist at both the CB1 and CB2 receptors. With a Ki of 1.2nM it is fairly selective for the CB1 subtype, its affinity at this subtype is measured at approximately 10x the affinity at CB2(12.4nM). It was discovered by and named after John W. Huffman.
JWH-015 is a chemical from the naphthoylindole family that acts as a subtype-selective cannabinoid agonist. Its affinity for CB2 receptors is 13.8 nM, while its affinity for CB1 is 383 nM, meaning that it binds almost 28 times more strongly to CB2 than to CB1. However, it still displays some CB1 activity, and in some model systems can be very potent and efficacious at activating CB1 receptors, and therefore it is not as selective as newer drugs such as JWH-133. It has been shown to possess immunomodulatory effects, and CB2 agonists may be useful in the treatment of pain and inflammation. It was discovered and named after John W. Huffman.
JWH-307 is an analgesic drug used in scientific research, which acts as a cannabinoid agonist at both the CB1 and CB2 receptors. It is somewhat selective for the CB2 subtype, with a Ki of 7.7 nM at CB1 vs 3.3 nM at CB2. It was discovered by, and named after, John W. Huffman. JWH-307 was detected as an ingredient in synthetic cannabis smoking blends in 2012, initially in Germany.
JWH-203 (1-pentyl-3-(2-chlorophenylacetyl)indole) is an analgesic chemical from the phenylacetylindole family that acts as a cannabinoid agonist with approximately equal affinity at both the CB1 and CB2 receptors, having a Ki of 8.0 nM at CB1 and 7.0 nM at CB2. It was originally discovered by, and named after, John W. Huffman, but has subsequently been sold without his permission as an ingredient of synthetic cannabis smoking blends. Similar to the related 2'-methoxy compound JWH-250, the 2'-bromo compound JWH-249, and the 2'-methyl compound JWH-251, JWH-203 has a phenylacetyl group in place of the naphthoyl ring used in most aminoalkylindole cannabinoid compounds, and has the strongest in vitro binding affinity for the cannabinoid receptors of any compound in the phenylacetyl group.
JWH-210 is an analgesic chemical from the naphthoylindole family, which acts as a potent cannabinoid agonist at both the CB1 and CB2 receptors, with Ki values of 0.46 nM at CB1 and 0.69 nM at CB2. It is one of the most potent 4-substituted naphthoyl derivatives in the naphthoylindole series, having a higher binding affinity (i.e. lower Ki) at CB1 than both its 4-methyl and 4-n-propyl homologues JWH-122 (CB1 Ki 0.69 nM) and JWH-182 (CB1 Ki 0.65 nM) respectively, and than the 4-methoxy compound JWH-081 (CB1 Ki 1.2 nM). It was discovered by and named after John W. Huffman.
JWH-007 is an analgesic chemical from the naphthoylindole family, which acts as a cannabinoid agonist at both the CB1 and CB2 receptors. It was first reported in 1994 by a group including the noted cannabinoid chemist John W. Huffman. It was the most active of the first group of N-alkyl naphoylindoles discovered by the team led by John W Huffman, several years after the family was initially described with the discovery of the N-morpholinylethyl compounds pravadoline (WIN 48,098), JWH-200 (WIN 55,225) and WIN 55,212-2 by the Sterling Winthrop group. Several other N-alkyl substituents were found to be active by Huffman's team including the n-butyl, n-hexyl, 2-heptyl, and cyclohexylethyl groups, but it was subsequently determined that the 2-methyl group on the indole ring is not required for CB1 binding, and tends to increase affinity for CB2 instead. Consequently, the 2-desmethyl derivative of JWH-007, JWH-018, has slightly higher binding affinity for CB1, with an optimum binding of 9.00 nM at CB1 and 2.94 nM at CB2, and JWH-007 displayed optimum binding of 9.50 nM at CB1 and 2.94 nM at CB2.
JWH-019 is an analgesic chemical from the naphthoylindole family that acts as a cannabinoid agonist at both the CB1 and CB2 receptors. It is the N-hexyl homolog of the more common synthetic cannabinoid compound JWH-018. Unlike the butyl homolog JWH-073, which is several times weaker than JWH-018, the hexyl homolog is only slightly less potent, although extending the chain one carbon longer to the heptyl homolog JWH-020 results in dramatic loss of activity. These results show that the optimum side chain length for CB1 binding in the naphthoylindole series is the five-carbon pentyl chain, shorter than in the classical cannabinoids where a seven-carbon heptyl chain produces the most potent compounds. This difference is thought to reflect a slightly different binding conformation adopted by the naphthoylindole compounds as compared to the classical cannabinoids, and may be useful in characterizing the active site of the CB1 and CB2 receptors.
A-796,260 is a drug developed by Abbott Laboratories that acts as a potent and selective cannabinoid CB2 receptor agonist. Replacing the aromatic 3-benzoyl or 3-naphthoyl group found in most indole derived cannabinoids with the 3-tetramethylcyclopropylmethanone group, imparts significant selectivity for CB2, and A-796,260 was found to be a highly selective CB2 agonist with little affinity for CB1, having a CB2Ki of 4.6 nM vs 945 nM at CB1. It has potent analgesic and anti-inflammatory actions in animal models, being especially effective in models of neuropathic pain, but without producing cannabis-like behavioral effects.
AM-1220 is a drug that acts as a potent and moderately selective agonist for the cannabinoid receptor CB1, with around 19 times selectivity for CB1 over the related CB2 receptor. It was originally invented in the early 1990s by a team led by Thomas D'Ambra at Sterling Winthrop, but has subsequently been researched by many others, most notably the team led by Alexandros Makriyannis at the University of Connecticut. The (piperidin-2-yl)methyl side chain of AM-1220 contains a stereocenter, so there are two enantiomers with quite different potency, the (R)-enantiomer having a Ki of 0.27 nM at CB1 while the (S)-enantiomer has a much weaker Ki of 217 nM.
UR-144 (TMCP-018, KM-X1, MN-001, YX-17) is a drug invented by Abbott Laboratories, that acts as a selective full agonist of the peripheral cannabinoid receptor CB2, but with much lower affinity for the psychoactive CB1 receptor.
JWH-120 is a synthetic cannabimimetic that was discovered by John W. Huffman. It is the N-propyl analog of JWH-122. It is a potent and selective ligand for the CB2 receptor, but a weaker ligand for the CB1 receptor. It has a binding affinity of Ki = 6.1 ± 0.7 nM at the CB2 subtype and 173 times selectivity over the CB1 subtype.
MAM-2201 is a drug that presumably acts as a potent agonist for the cannabinoid receptors. It had never previously been reported in the scientific or patent literature, and was first identified by laboratories in the Netherlands and Germany in June 2011 as an ingredient in synthetic cannabis smoking blends. Like RCS-4 and AB-001, MAM-2201 thus appears to be a novel compound invented by "research chemical" suppliers specifically for grey-market recreational use. Structurally, MAM-2201 is a hybrid of two known cannabinoid compounds JWH-122 and AM-2201, both of which had previously been used as active ingredients in synthetic cannabis blends before being banned in many countries.
EAM-2201 is a drug that presumably acts as a potent agonist for the cannabinoid receptors. It had never previously been reported in the scientific or patent literature, and was first identified by laboratories in Japan in July 2012 as an ingredient in synthetic cannabis smoking blends Like the closely related MAM-2201 which had been first reported around a year earlier, EAM-2201 thus appears to be another novel compound invented by designer drug suppliers specifically for recreational use. Structurally, EAM-2201 is a hybrid of two known cannabinoid compounds JWH-210 and AM-2201, both of which had previously been used as active ingredients in synthetic cannabis blends before being banned in many countries.
FUB-JWH-018 is a naphthoylindole-based synthetic cannabinoid, representing a molecular hybrid of JWH-018 and AB-FUBICA or ADB-FUBICA.
JWH-309 (naphthalen-1-yl-(5-naphthalen-1-yl-1-pentylpyrrol-3-yl)methanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as an agonist of the CB1 (Ki = 41 ± 3nM) and CB2 (Ki = 49 ± 7nM) receptors, displaying a slight selectivity for the former. JWH-309 was first synthesized in 2006 by John W. Huffman and colleagues to examine the nature of ligand binding to the CB1 receptor.
JWH-367 ([5-(3-methoxyphenyl)-1-pentylpyrrol-3-yl]-naphthalen-1-ylmethanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as an agonist of the CB1 (Ki = 53 ± 2nM) and CB2 (Ki = 23 ± 1nM) receptors, binding ~2.3 times stronger to the CB2 receptor than to the CB1 receptor. JWH-367 was first synthesized in 2006 by John W. Huffman and colleagues to examine the nature of ligand binding to the CB1 receptor.
JWH-366 (naphthalen-1-yl-(1-pentyl-5-pyridin-3-ylpyrrol-3-yl)methanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as an agonist of the CB1 (Ki = 191 ± 12nM) and CB2 (Ki = 24 ± 1nM) receptors, with a strong (~8x) selectivity for the CB2 receptor over the CB1 receptor. JWH-366 was first synthesized in 2006 by John W. Huffman and colleagues to examine the nature of ligand binding to the CB1 receptor.
JWH-363 (1-Naphthyl{1-pentyl-5-[3-(trifluoromethyl)phenyl]-1H-pyrrol-3-yl}methanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as an agonist of the CB1 (Ki = 245 ± 5nM) and CB2 (Ki = 71 ± 1nM) receptors, with a moderate (~3.45x) selectivity for the latter. JWH-363 was first synthesized in 2006 by John W. Huffman and colleagues to examine the nature of ligand binding to the CB1 receptor.
JWH-146 (1-heptyl-5-phenyl-1H-pyrrol-3-yl)-1-naphthalenyl-methanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as an agonist of the CB1 (Ki = 21 ± 2nM) and CB2 (Ki = 62 ± 5nM) receptors, with a moderate (~2.9x) selectivity for the CB1 receptor over the CB2 receptor. JWH-146 was first synthesized in 2006 by John W. Huffman and colleagues to examine the nature of ligand binding to the CB1 receptor.
JWH-150 ((1-butyl-5-phenylpyrrol-3-yl)-naphthalen-1-ylmethanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as an agonist of the CB1 (Ki = 60 ± 1nM) and CB2 (Ki = 15 ± 2nM) receptors, with a moderate (4x) selectivity for the CB2 receptor. JWH-150 was first synthesized in 2006 by John W. Huffman and colleagues to examine the nature of ligand binding to the CB1 receptor.
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