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JWH-176

JWH-176
Legal status
Legal status
Identifiers
  • 1-([(1E)-3-Pentylinden-1-ylidine]methyl)naphthalene
CAS Number
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC25H24
Molar mass324.467 g·mol−1
3D model (JSmol)
  • CCCCCC1=C\C(=C/c2cccc3ccccc32)c2ccccc21
  • InChI=1S/C25H24/c1-2-3-4-11-21-18-22(25-16-8-7-15-24(21)25)17-20-13-9-12-19-10-5-6-14-23(19)20/h5-10,12-18H,2-4,11H2,1H3/b22-17+
  • Key:FPESBQVTVSBBSE-OQKWZONESA-N
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JWH-176 is an analgesic drug which acts as a cannabinoid receptor agonist. Its binding affinity at the CB1 receptor is 26.0 nM, making it more potent than THC itself,[1] however JWH-176 is particularly notable in that it is a hydrocarbon containing no heteroatoms. This demonstrates that reasonably high-affinity cannabinoid binding and agonist effects can be produced by compounds with no hydrogen bonding capacity at all, relying merely on Van der Waals and possibly hydrophobic interactions to bind to the receptor.[2] It was discovered by, and named after, John W. Huffman.

  1. ^ Huffman JW, Padgett LW (2005). "Recent developments in the medicinal chemistry of cannabimimetic indoles, pyrroles and indenes". Current Medicinal Chemistry. 12 (12): 1395–411. doi:10.2174/0929867054020864. PMID 15974991.
  2. ^ Pertwee RG. Cannabinoids. Handbook of Experimental Pharmacology. Vol. 168. Springer. p. 269. ISBN 3-540-22565-X.
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