JWH-176

JWH-176

Legal status
Legal status	In general: legal
Identifiers
IUPAC name 1-([(1E)-3-pentylinden-1-ylidine]methyl)naphthalene
CAS Number	619294-62-1 Y
ChemSpider	29341653
Chemical and physical data
Formula	C25H24
Molar mass	324.457 g/mol
3D model (JSmol)	Interactive image
SMILES CCCCCc(c3)c1ccccc1c3=Cc2cccc4ccccc24
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-XLNRJJMWSA-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 only 26.0nM, 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 interactions to bind to the receptor.^[2] It was discovered by, and named after, Dr. John W. Huffman.

See also

• JWH-175

References

1. ↑ Huffman JW, Padgett LW. Recent Developments in the Medicinal Chemistry of Cannabimimetic Indoles, Pyrroles and Indenes. Current Medicinal Chemistry, 2005; 12: 1395-1411.
2. ↑ Roger Pertwee. Cannabinoids. Handbook of Experimental Pharmacology Volume 168, p 269. Springer. ISBN 3-540-22565-X