JWH-176

JWH-176
Legal status
Legal status	UK: Class B; US: Schedule I;
Identifiers
	IUPAC name 1-([(1E)-3-Pentylinden-1-ylidine]methyl)naphthalene;
CAS Number	619294-62-1 ;
ChemSpider	29341653;
UNII	VA60GT97BB;
CompTox Dashboard (EPA)	DTXSID70692895 ;
Chemical and physical data
Formula	C25H24
Molar mass	324.467 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCC1=C\C(=C/c2cccc3ccccc32)c2ccccc21;
	InChI 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;
	(verify)

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.

^ 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.
^ Pertwee RG. Cannabinoids. Handbook of Experimental Pharmacology. Vol. 168. Springer. p. 269. ISBN 3-540-22565-X.

[pmid15974991-1] 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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