List of JWH cannabinoids

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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 Ki 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 Ki 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 Ki 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 Ki of 87nM, making it roughly half the potency of THC.
  • JWH-047 — a potent and selective agonist for the CB2 receptor with a Ki of 0.9 nM, and a Ki 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 Ki of 0.49 nM ± 0.1, and a Ki 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 Ki 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 Ki 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 Ki 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 Ki 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 Ki of 52 ± 5 nM[3]
  • JWH-120 — a potent and 173-fold selective CB2 agonist with a Ki 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 Ki 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 Ki 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 Ki 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 Ki = 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 Ki 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 Ki of 19.0nM
  • JWH-164 — a potent cannabinoid agonist with a Ki 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 Ki 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 Ki 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 Ki 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 Ki 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 Ki 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 Ki 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 Ki) 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 Ki 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 Ki 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 Ki 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 Ki 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 Ki 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 Ki 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 (Ki=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 Ki 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 Ki 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 Ki of 2.3nM at CB1 and 2.8nM at CB2.[7]
  • JWH-424 — a potent and moderately selective CB2 agonist with a Ki of 5.44nM at CB2 and 20.9nM at CB1.

See also[edit]

References[edit]

  1. ^ a b c d e f g h i j 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. ^ a b c d e 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. doi:10.1038/sj.bjp.0707567. PMC 2219524. PMID 17982473.  edit
  3. ^ a b c d e f g h i j k l m n o 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.  edit
  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.   edit
  6. ^ a b c d e f g 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.