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JWH-146

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Chemical compound Pharmaceutical compound
JWH-146
Legal status
Legal status
Identifiers
IUPAC name
  • (1-heptyl-5-phenyl-1H-pyrrol-3-yl)-1-naphthalenyl-methanone
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC28H29NO
Molar mass395.546 g·mol
3D model (JSmol)
SMILES
  • O=C(C1=CC=CC2=C1C=CC=C2)C3=CN(CCCCCCC)C(C4=CC=CC=C4)=C3
InChI
  • InChI=1S/C28H29NO/c1-2-3-4-5-11-19-29-21-24(20-27(29)23-14-7-6-8-15-23)28(30)26-18-12-16-22-13-9-10-17-25(22)26/h6-10,12-18,20-21H,2-5,11,19H2,1H3
  • Key:JDBFNFBWXVCTSA-UHFFFAOYSA-N

JWH-146 (1-heptyl-5-phenyl-1H-pyrrol-3-yl)-1-naphthalenyl-methanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as an agonist of the CB1 (Ki = 21 ± 2nM) and CB2 (Ki = 62 ± 5nM) receptors, with a moderate (~2.9x) selectivity for the CB1 receptor over the CB2 receptor. JWH-146 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-146 is not federally scheduled, although some states have passed legislation banning the sale, possession, and manufacture of JWH-146.

In Canada, JWH-146 and other naphthoylpyrrole-based cannabinoids are Schedule II controlled substances under the Controlled Drugs and Substances Act.

In the United Kingdom, JWH-146 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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