JWH-175

JWH-175 is a drug from the naphthylmethylindole family which acts as a cannabinoid receptor agonist. It was invented by the scientist John W. Huffman and colleagues at Clemson University. JWH-175 is closely related to the widely used cannabinoid designer drug JWH-018, but with the ketone bridge replaced by a simpler methylene bridge. It is several times weaker than JWH-018, having a binding affinity at the CB1 receptor of 22 nM, though some derivatives substituted at the 4-position of the naphthyl ring have potency more closely approaching that of the equivalent naphthoylindoles.[1] This makes JWH-175 considerably less potent than most synthetic cannabinoid drugs used in synthetic cannabis blends, and it is unclear if JWH-175 has ever been used for this purpose. However it has still been explicitly banned in several jurisdictions including Russia and some Australian states, in order to stop its potential use as an ingredient in such products. In the United States, all CB1 receptor agonists of the 3-(1-naphthylmethane)indole class such as JWH-175 are Schedule I Controlled Substances.[2]

JWH-175
Legal status
Legal status
  • AU: Illegal
  • UK: Illegal
  • US: Schedule I
  • Illegal in Russia
Identifiers
IUPAC name
  • (1-Pentylindol-3-yl)naphthalen-1-ylmethane
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC24H25N
Molar mass327.471 g·mol−1
3D model (JSmol)
SMILES
  • c3cccc2c3cccc2Cc(cn4CCCCC)c1ccccc14
InChI
  • InChI=1S/C24H25N/c1-2-3-8-16-25-18-21(23-14-6-7-15-24(23)25)17-20-12-9-11-19-10-4-5-13-22(19)20/h4-7,9-15,18H,2-3,8,16-17H2,1H3 N
  • Key:TYBRSILIYTUTSQ-UHFFFAOYSA-N N
 NY (what is this?)

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. 21 U.S.C. § 812: Schedules of controlled substances
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