JWH-164

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JWH-164
JWH-164 structure.png
Systematic (IUPAC) name
7-methoxynaphthalen-1-yl-(1-pentylindol-3-yl)methanone
Clinical data
Legal status
?
Identifiers
CAS number 824961-61-7
ATC code ?
PubChem CID 45271217
ChemSpider 24618407
Chemical data
Formula C25H25NO2 
Mol. mass 371.471 g/mol
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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 6.9nM 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[edit]

  1. ^ Huffman JW, et al. 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