JWH-369

JWH-369 ((5-(2-chlorophenyl)-1-pentyl-1H-pyrrol-3-yl)(naphthalen-1-yl)methanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as a potent agonist of the CB1 (Ki = 7.9 ± 0.4nM) and CB2 (Ki = 5.2 ± 0.3nM) receptors, with a slight selectivity for the latter. JWH-369 was first synthesized in 2006 by John W. Huffman and colleagues to examine the nature of ligand binding to the CB1 receptor.[1]

JWH-369
Legal status
Legal status
Identifiers
  • (5-(2-chlorophenyl)-1-pentyl-1H-pyrrol-3-yl)(naphthalen-1-yl)methanone
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC26H24ClNO
Molar mass401.93 g·mol−1
3D model (JSmol)
  • O=C(C=1C=C(C=2C=CC=CC2Cl)N(C1)CCCCC)C3=CC=CC=4C=CC=CC43
  • InChI=1S/C26H24ClNO/c1-2-3-8-16-28-18-20(17-25(28)23-13-6-7-15-24(23)27)26(29)22-14-9-11-19-10-4-5-12-21(19)22/h4-7,9-15,17-18H,2-3,8,16H2,1H3 checkY
  • Key:SUELCWQJMQQCTF-UHFFFAOYSA-N checkY

Legality

In the United States JWH-369 is not federally scheduled, although some states have passed legislation banning the sale, possession, and manufacture of JWH-369.[2][3][4][5]

In Canada, JWH-369 and other naphthoylpyrrole-based cannabinoids are Schedule II controlled substances under the Controlled Drugs and Substances Act.

In the United Kingdom, JWH-369 and other naphthoylpyrrole-based cannabinoids are considered Class B drugs under the Misuse of Drugs Act 1971.

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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