JWH-164

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JWH-164
File:JWH-164 structure.png
Systematic (IUPAC) name
7-methoxynaphthalen-1-yl-(1-pentylindol-3-yl)methanone
Identifiers
PubChem CID 45271217
Chemical data
Formula C25H25NO2
Molar mass 371.471 g/mol[[Script error: No such module "String".]]
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JWH-164 is a synthetic cannabinoid receptor agonist from the naphthoylindole family. It has approximately equal affinity for the CB1 and CB2 receptors, with a Ki of 6.6nM at CB1 and 6.9 nM at CB2. JWH-164 is a positional isomer of the related compound JWH-081, but with a methoxy group at the 7-position of the naphthyl ring, rather than the 4-position as in JWH-081. Its potency is intermediate between that of JWH-081 and its ring unsubstituted derivative JWH-018, demonstrating that substitution of the naphthyl 7-position can also result in increased cannabinoid receptor binding affinity.[1][2]


References

  1. ↑ Huffman JW, Zengin G, Wu MJ, Lu J, Hynd G, Bushell K, Thompson ALS, Bushell S, Tartal C, Hurst DP, Reggio PH, Selley DE, Cassidy MP, Wiley JL, Martin BR. Structure–activity relationships for 1-alkyl-3-(1-naphthoyl)indoles at the cannabinoid CB1 and CB2 receptors: steric and electronic effects of naphthoyl substituents. New highly selective CB2 receptor agonists. Bioorganic and Medicinal Chemistry. 2005; 13:89-112. PMID 15582455
  2. ↑ Huffman JW, Padgett LW. Recent Developments in the Medicinal Chemistry of Cannabimimetic Indoles, Pyrroles and Indenes. Current Medicinal Chemistry, 2005; 12: 1395-1411. PMID 15974991
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