JWH-176

JWH-176
Legal status
Legal status
Identifiers
IUPAC name
  • 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)
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.

Stereochemistry

JWH-176 is the (E)-stereoisomer of 1-([3-pentylinden-1-ylidine]methyl)naphthalene, whereas JWH-171 is the mixture of the (E)- and (Z)-isomers.[3]

JWH-171

In the United States, CB1 receptor agonists of the 1-(1-naphthylmethylene)indene class such as JWH-176 and JWH-171 are Schedule I Controlled Substances.[4]

As of 23 December 2009, any compound structurally derived from 1–(1–naphthylmethyl)indene by substitution at the 3–position of the indene ring by an alkyl group is a Class B drug in the United Kingdom.[5]

See also

References

  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.
  3. ↑ Huffman JW, Padgett LW (10 December 2010). "Recent Developments in the Medicinal Chemistry of Cannabimimetic Indoles, Pyrroles and Indenes". In Rahman A, Iqbal Choudhary M, Reitz AB (eds.). Frontiers in Medicinal Chemistry. Vol. 4. pp. 661–687 (681). doi:10.2174/978160805207310904010661. ISBN 978-1-60805-346-9.
  4. ↑ 21 U.S.C. § 812: Schedules of controlled substances
  5. ↑ "The Misuse of Drugs Act 1971 (Amendment) Order 2009", legislation.gov.uk, The National Archives, SI 2009/3209
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