THC Science

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 ;
ChemSpider	29341653;
CompTox Dashboard (EPA)	DTXSID70692895 ;
Chemical and physical data
Formula	C25H24
Molar mass	324.457 g/mol g·mol−1
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;
	(verify)

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.

References

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

[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

[1]

[2]

@@ Line 3: / Line 3: @@
 | verifiedrevid = 437691572
 | IUPAC_name = 1-([(1E)-3-pentylinden-1-ylidine]methyl)naphthalene
-| image = JWH-171.png
+| image = JWH-176.svg
 | width = 180

THC Science

Bringing Science to the Cannabis Conversation!

Cannabis Ruderalis

Revision as of 08:21, 20 March 2018

See also

References

Leave a Reply

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
CompTox Dashboard (EPA)	DTXSID70692895
Chemical and physical data
Formula	C₂₅H₂₄
Molar mass	324.457 g/mol g·mol⁻¹
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
(verify)