List of JWH cannabinoids

The John W. Huffman research group at Clemson University synthesized over 450 cannabinoids. Some of those are:

• JWH-007 — an analgesic chemical from the naphthoylindole family, which acts as a cannabinoid agonist at both the CB₁ receptor and CB₂ receptors, with some selectivity for CB₂ with a K_i of 2.9nM ± 2.6 and 9.5nM ± 4.5 at CB₁.^[1]
• JWH-015 — a chemical from the naphthoylindole family, which acts as a subtype-selective cannabinoid agonist. Its affinity for CB₂ receptors is 13.8nM, while its affinity for CB₁ is 383nM, meaning that it binds almost 28x more strongly to CB₂ than CB₁.^[1]
• JWH-018 — an analgesic chemical from the naphthoylindole family, which acts as a full agonist at both the CB₁ and CB₂ cannabinoid receptors, with some selectivity for CB₂ with a K_i of 2.9nM ± 2.6 and 9nM ± 5 at CB₁.^[1] It is found in some forms of synthetic cannabis.
• JWH-019 — an agonist at both CB₁ and CB₂ receptors, it has 1.77x selectivity for CB₂ with a K_i of 5.55nM ± 2 and 9.8nM ± 2 at CB₁.
• JWH-030 — an analgesic chemical from the naphthoylpyrrole family, it is a partial agonist at CB₁ receptors, with a K_i of 87nM, making it roughly half the potency of THC.
• JWH-047 — a potent and selective agonist for the CB₂ receptor with a K_i of 0.9 nM, and a K_i of 59 ± 3 nM at CB₁, it has a 65x selectivity for CB₂.^[1]
• JWH-048 — a potent and selective agonist for the CB₂ receptor with a K_i of 0.49 nM ± 0.1, and a K_i of 10.7 nM ± 1.0 at CB₁, it has a 22x selectivity for CB₂.^[1]
• JWH-051 — an analgesic, it has high affinity for the CB₁ receptor, but is a much stronger agonist for CB₂, with a K_i value of 0.03nM at CB₂ vs 1.20nM at CB₁. It was one of the first CB₂-selective ligands developed, although its selectivity for CB₂ is modest compared to newer compounds such as HU-308.
• JWH-057 — a 1-deoxy analog of Δ8-THC that has very high affinity for the CB₂ receptor, but also has high affinity for the CB₁ receptor.^[2]
• JWH-073 — an analgesic chemical from the naphthoylindole family, which acts as a cannabinoid agonist at both the CB₁ and CB₂ receptors. It is somewhat selective for the CB₁ subtype with a K_i of 8.9nM. It is found in some forms of synthetic cannabis.
• JWH-081 — an analgesic chemical from the naphthoylindole family, which acts as an agonist at both the cannabinoid receptors with a K_i of 1.2nM ± 0.03 at CB₁^[3] and 12.4nM ± 2.2 at the CB₂ receptors. It is fairly selective for the CB₁ subtype with approximately 10x the affinity for CB₂. It is found in some forms of synthetic cannabis.
• JWH-098 — a potent and fairly selective CB₂ agonist with a K_i of 1.9nM ± 0.3 at CB₂ and 4.5nM ± 0.1 at CB₁,^[3] giving it about 2.4x selectivity for CB₂.
• JWH-116 — a CB₁ ligand with a K_i of 52 ± 5 nM^[3]
• JWH-120 — a potent and 173-fold selective CB₂ agonist with a K_i of 6.1nM ± 0.7, it is the N-propyl homolog of JWH-122.^[2]
• JWH-122 — a potent and fairly selective CB₁ agonist with a K_i of 0.69nM ± 0.5 at CB₁ and 1.2nM ± 1.2 at CB₂. It is found in some forms of synthetic cannabis.
• JWH-133 — a potent and highly selective CB₂ receptor agonist with a K_i of 3.4nM and selectivity of around 200x for CB₂ over CB₁ receptors.^[1]
• JWH-139 — 3-(1,1-dimethylpropyl)-6,6,9-trimethyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromene^[4]
• JWH-147 — an analgesic drug from the naphthoylpyrrole family, which acts as a cannabinoid agonist at both the CB₁ and CB₂ receptors. It is somewhat selective for the CB₂ subtype, with a K_i of 11.0nM at CB₁ vs 7.1nM at CB₂.
• JWH-148 — a moderately selective ligand for the CB₂ receptor, with a binding affinity of K_i = 14.0 ± 1.0 nM at this subtype, and more than 8 times selectivity over the CB₁ subtype.^[5]
• JWH-149 — a potent and fairly selective CB₂ agonist with a K_i of 0.73nM ± 0.03 and 5.0nM ± 2.1 at CB₁,^[3] giving it about 6.8x selectivity for CB₂.
• JWH-161 — a CB1 ligand with K_i of 19.0nM
• JWH-164 — a potent cannabinoid agonist with a K_i of 6.6nM ± 0.7 at CB₁ and 6.9nM ± 0.2 at CB₂.
• JWH-166 — a potent and highly selective CB₂ agonist with a K_i of 1.9nM ± 0.08 at CB₂ and 44nM ± 10 at CB₁ giving it 23x selectivity for CB₂.^[1]
• JWH-167 — a weak cannabinoid agonist from the phenylacetylindole family with 1.77x selectivity for CB₁ with a K_i of 90nM ± 17 at CB₁ and 159nM ± 14 at CB₂.^[6]
• JWH-171 — an analgesic drug which acts as a cannabinoid receptor agonist. Its binding affinity at the CB₁ receptor is only 51nM, making it slightly less potent than THC itself.
• JWH-175 — (1-pentylindol-3-yl)naphthalen-1-ylmethane, 22nM at CB₁^[3]
• JWH-176 — 1-([(1E)-3-pentylinden-1-ylidine]methyl)naphthalene, 26nM at CB₁^[3]
• JWH-181 — a potent cannabinoid agonist with 2.1x selectivity for CB₂ with a K_i of 0.62nM ± 0.04 and 1.3nM ± 0.1 at CB₁.
• JWH-182 — a potent cannabinoid agonist with some selectivity for CB₁ with a K_i of 0.65nM ± 0.03 and 1.1nM ± 0.1 at CB₂.
• JWH-184 — 1-pentyl-1H-indol-3-yl-(4-methyl-1-naphthyl)methane, 23nM at CB₁^[3]
• JWH-185 — 1-pentyl-1H-indol-3-yl-(4-methoxy-1-naphthyl)methane, 17nM at CB₁^[3]
• JWH-192 — (1-(2-morpholin-4-ylethyl)indol-3-yl)-4-methylnaphthalen-1-ylmethane, 41nM at CB₁^[3]
• JWH-193 — (1-(2-morpholin-4-ylethyl)indol-3-yl)-4-methylnaphthalen-1-ylmethanone, 6nM at CB₁^[3]
• JWH-194 — 2-methyl-1-pentyl-1H-indol-3-yl-(4-methyl-1-naphthyl)methane, 127nM at CB₁^[3]
• JWH-195 — (1-(2-morpholin-4-ylethyl)indol-3-yl)-naphthalen-1-ylmethane, 113nM at CB₁^[3]
• JWH-196 — 2-methyl-3-(1-naphthalenylmethyl)-1-pentyl-1H-Indole, 151nM ± 18 at CB₁
• JWH-197 — 2-methyl-1-pentyl-1H-indol-3-yl-(4-methoxy-1-naphthyl)methane, 323nM at CB₁^[3]
• JWH-198 — (1-(2-morpholin-4-ylethyl)indol-3-yl)-4-methoxynaphthalen-1-ylmethanone, 10nM at CB₁^[3]
• JWH-199 — (1-(2-morpholin-4-ylethyl)indol-3-yl)-4-methoxynaphthalen-1-ylmethane, 20nM at CB₁^[3]
• JWH-200 — an analgesic chemical from the aminoalkylindole family, which acts as a cannabinoid receptor agonist. Its binding affinity at the CB₁ receptor is 42nM, around the same as that of THC, but interestingly, its analgesic potency in vivo was higher than that of other analogues with stronger CB₁ binding affinity in vitro, around 3 times that of THC but with less sedative effect, most likely reflecting favorable pharmacokinetic characteristics. It is found in some forms of synthetic cannabis.
• JWH-203 — an analgesic chemical from the phenylacetylindole family, which acts as a cannabinoid agonist with approximately equal affinity at both the CB₁ and CB₂ receptors, having a K_i of 8.0nM at CB₁ and 7.0nM at CB₂. Similar to the related 2'-methoxy compound JWH-250, JWH-203 has a phenylacetyl group in place of the naphthoyl ring used in most aminoalkylindole cannabinoid compounds, and is the most potent compound found in the phenylacetyl group.^[6] It is found in some forms of synthetic cannabis.
• JWH-205 — 1-(2-methyl-1-pentylindol-3-yl)-2-phenylethanone, CB₁: 124nM ± 23 CB₂: 180nM ± 9 CB₂ selectivity: 1.45x^[6]
• JWH-210 — an analgesic chemical from the naphthoylindole family, which acts as a potent cannabinoid agonist at both the CB₁ and CB₂ receptors, with K_i values of 0.46nM at CB₁ and 0.69nM 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 K_i) at CB₁ than both its 4-methyl and 4-n-propyl homologues (JWH-122 and JWH-182 respectively), and than the 4-methoxy compound JWH-081.^[1] It is found in some forms of synthetic cannabis.
• JWH-213 — a potent and fairly selective CB₂ agonist with a K_i of 0.42nM ± 0.05 at CB₂ and 1.5nM ± 0.2 at CB₁ giving it 3.6x selectivity over CB₁.^[1]
• JWH-220 — 19nM at CB₁
• JWH-229 — 1-methoxy-3-(1',1'-dimethylhexyl)-Δ⁸-THC, a dibenzopyran "classical" cannabinoid drug with a K_i of 4.6nM ± 2.0, it is a potent CB₂ agonist.
• JWH-234 — a cannabinoid agonist that has 2.2x selectivity for CB₂ with a K_i value of 8.4nM ± 1.8 at CB₂ and 3.8nM ± 0.6 at CB₁.
• JWH-249 — CB₁: 8.4nM ± 1.8 CB₂: 20nM ± 2 selectivity for CB₁: 2.38x^[6]
• JWH-250 — an analgesic chemical from the phenylacetylindole family, which acts as a cannabinoid agonist at both the CB₁ and CB₂ receptors, with a K_i of 11nM at CB₁ and 33nM at CB₂.^[6] It is found in some forms of synthetic cannabis.
• JWH-251 — (1-pentyl-3-(2-methylphenylacetyl)indole) CB₁: 29nM ± 3 CB₂: 146nM ± 36 selectivity for CB₁: 5x^[6]
• JWH-253 —
• JWH-258 — a potent and mildly selective CB₁ agonist with a K_i of 4.6nM ± 0.6 and 10.5nM ± 1.3 at CB₂.^[1]
• JWH-300 — CB₁: 116nM CB₂: 5.3nM^[2]
• JWH-302 — (1-pentyl-3-(3-methoxyphenylacetyl)indole) CB₁: 17nM ± 2 CB₂: 89nM ± 15 selectivity for CB₁: 5.26x^[6]
• JWH-307 — an analgesic drug from the naphthoylpyrrole family, which acts as a cannabinoid agonist at both the CB₁ and CB₂ receptors. It is somewhat selective for the CB₂ subtype, with a K_i of 7.7nM at CB₁ vs 3.3nM at CB₂.
• JWH-336 — CB₁: ~1.2nM CB₂: 36nM^[2]
• JWH-350 — an 11-nor-1-methoxy-3-(1',1'-dimethylheptyl)-9α-hydroxyhexahydrocannabinol with 33-fold selectivity for the CB₂ receptor and high CB₂ receptor affinity (K_i=12nM ± 1) has the desirable combination of excellent CB₂ affinity combined with little affinity for the CB₁ receptor.^[2]
• JWH-359 — a dibenzopyran "classical" cannabinoid drug with a K_i of 13.0nM and selectivity of around 220x for CB₂, it is a potent and selective CB₂ receptor agonist.
• JWH-387 — 1-pentyl-3-(4-bromo-1-naphthoyl)indole, an analgesic chemical from the naphthoylindole family, which acts as a potent cannabinoid agonist at both receptors with a K_i of 1.2nM at CB₁ and 1.1nM at CB₂.
• JWH-398 — an analgesic chemical from the naphthoylindole family, which acts as a potent cannabinoid agonist at both receptors with a K_i of 2.3nM at CB₁ and 2.8nM at CB₂.^[7]
• JWH-424 — a potent and moderately selective CB₂ agonist with a K_i of 5.44nM at CB₂ and 20.9nM at CB₁.

See also

• List of AM cannabinoids
• List of CP cannabinoids
• List of HU cannabinoids
• List of miscellaneous designer cannabinoids

References

1. 1 2 3 4 5 6 7 8 9 10 Huffman JW, Zengin G, Wu MJ, Lu J, Hynd G, Bushell K, Tartal C, Hurst DP, Reggio PH, Selley DE, Cassidy MP, Wiley JL, Martin BR (2005). "Structure-activity relationships for 1-alkyl-3-(1-naphthoyl)indoles at the cannabinoid CB(1) and CB(2) receptors: steric and electronic effects of naphthoyl substituents. New highly selective CB(2) receptor agonists". Bioorganic & Medicinal Chemistry Letters. 13 (1): 89–112. PMID 15582455. doi:10.1016/j.bmc.2004.09.050. 
2. 1 2 3 4 5 Poso, A.; Huffman, J. W. (2008). "Targeting the cannabinoid CB2 receptor: modelling and structural determinants of CB2 selective ligands". British Journal of Pharmacology. 153 (2): 335–46. PMC 2219524 . PMID 17982473. doi:10.1038/sj.bjp.0707567. 
3. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 Huffman JW, Mabon R, Wu MJ, Lu J, Hart R, Hurst DP, Reggio PH, Wiley JL, Martin BR (2003). "3-Indolyl-1-naphthylmethanes: New Cannabimimetic Indoles Provide Evidence for Aromatic Stacking Interactions with the CB1 Cannabinoid Receptor". Bioorganic & Medicinal Chemistry Letters. 11 (4): 539–549. PMID 12538019. doi:10.1016/S0968-0896(02)00451-0. 
4. ↑ Howlett, A. C.; Barth, F; Bonner, TI; Cabral, G; Casellas, P; Devane, WA; Felder, CC; Herkenham, M; MacKie, K (2002). "International Union of Pharmacology. XXVII. Classification of Cannabinoid Receptors". Pharmacological Reviews. 54 (2): 161–202. PMID 12037135. doi:10.1124/pr.54.2.161. 
5. ↑ Huffman, J.; et al. (2005). "Structure-activity relationships for 1-alkyl-3-(1-naphthoyl)indoles at the cannabinoid CB(1) and CB(2) receptors: steric and electronic effects of naphthoyl substituents. New highly selective CB(2) receptor agonists.". Bioorganic & Medicinal Chemistry. 13 (1): 89–112. PMID 15582455. doi:10.1016/j.bmc.2004.09.050. 
6. 1 2 3 4 5 6 7 Huffman JW, Szklennik PV, Almond A, Bushell K, Selley DE, He H, Cassidy MP, Wiley JL, Martin BR (2005). "1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles". Bioorganic & Medicinal Chemistry Letters. 15 (18): 4110–3. PMID 16005223. doi:10.1016/j.bmcl.2005.06.008. 
7. ↑ "The Cannabinoid Receptors". doi:10.1007/978-1-59745-503-9. Retrieved 28 August 2013.