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JWH-309

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Chemical compound Pharmaceutical compound
JWH-309
Legal status
Legal status
Identifiers
IUPAC name
  • naphthalen-1-yl-(5-naphthalen-1-yl-1-pentylpyrrol-3-yl)methanone
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC30H27NO
Molar mass417.552 g·mol
3D model (JSmol)
SMILES
  • CCCCCN1C=C(C=C1C2=CC=CC3=CC=CC=C32)C(=O)C4=CC=CC5=CC=CC=C54
InChI
  • InChI=1S/C30H27NO/c1-2-3-8-19-31-21-24(30(32)28-18-10-14-23-12-5-7-16-26(23)28)20-29(31)27-17-9-13-22-11-4-6-15-25(22)27/h4-7,9-18,20-21H,2-3,8,19H2,1H3
  • Key:WVISOUYKTUUDFW-UHFFFAOYSA-N

JWH-309 (naphthalen-1-yl-(5-naphthalen-1-yl-1-pentylpyrrol-3-yl)methanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as an agonist of the CB1 (Ki = 41 ± 3nM) and CB2 (Ki = 49 ± 7nM) receptors, displaying a slight selectivity for the former. JWH-309 was first synthesized in 2006 by John W. Huffman and colleagues to examine the nature of ligand binding to the CB1 receptor.

Legality

In the United States JWH-309 is not federally scheduled, although some states have passed legislation banning the sale, possession, and manufacture of JWH-309.

In Canada, JWH-309 and other naphthoylpyrrole-based cannabinoids are Schedule II controlled substances under the Controlled Drugs and Substances Act.

In the United Kingdom, JWH-309 and other naphthoylpyrrole-based cannabinoids are considered Class B drugs under the Misuse of Drugs Act 1971.

See also

References

  1. Huffman JW, Padgett LW, Isherwood ML, Wiley JL, Martin BR (October 2006). "1-Alkyl-2-aryl-4-(1-naphthoyl)pyrroles: new high affinity ligands for the cannabinoid CB1 and CB2 receptors". Bioorganic & Medicinal Chemistry Letters. 16 (20): 5432–5. doi:10.1016/j.bmcl.2006.07.051. PMID 16889960.
  2. 21 U.S.C. § 812: Schedules of controlled substances
  3. "The 2020 Florida Statutes". www.leg.state.fl.us. Retrieved 20 August 2021.
  4. "Arizona Revised Statutes Title 13. Criminal Code § 13-3401". www.azleg.gov. Retrieved 20 August 2021.
  5. "California Code, Health and Safety Code - HSC § 11357.5". Findlaw.
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