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 — a 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 HU cannabinoids
• List of CP cannabinoids
• List of miscellaneous designer cannabinoids

References

1. 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. doi:10.1016/j.bmc.2004.09.050. PMID 15582455.
2. 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. doi:10.1038/sj.bjp.0707567. PMC 2219524. PMID 17982473.
3. 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. doi:10.1016/S0968-0896(02)00451-0. PMID 12538019.
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. doi:10.1124/pr.54.2.161. PMID 12037135.
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. doi:10.1016/j.bmc.2004.09.050. PMID 15582455.
6. 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. doi:10.1016/j.bmcl.2005.06.008. PMID 16005223.
7. "The Cannabinoid Receptors". doi:10.1007/978-1-59745-503-9. Retrieved 28 August 2013.