JWH-366

JWH-366 (naphthalen-1-yl-(1-pentyl-5-pyridin-3-ylpyrrol-3-yl)methanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as an agonist of the CB1 (Ki = 191 ± 12nM) and CB2 (Ki = 24 ± 1nM) receptors, with a strong (~8x) selectivity for the CB2 receptor over the CB1 receptor. JWH-366 was first synthesized in 2006 by John W. Huffman and colleagues to examine the nature of ligand binding to the CB1 receptor.[1]

JWH-366
Legal status
Legal status
Identifiers
  • naphthalen-1-yl-(1-pentyl-5-pyridin-3-ylpyrrol-3-yl)methanone
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC25H24N2O
Molar mass368.480 g·mol−1
3D model (JSmol)
  • CCCCCN1C=C(C=C1C2=CN=CC=C2)C(=O)C3=CC=CC4=CC=CC=C43
  • InChI=1S/C25H24N2O/c1-2-3-6-15-27-18-21(16-24(27)20-11-8-14-26-17-20)25(28)23-13-7-10-19-9-4-5-12-22(19)23/h4-5,7-14,16-18H,2-3,6,15H2,1H3 checkY
  • Key:MPQYTRCOFXNOTB-UHFFFAOYSA-N checkY

Legality

In the United States JWH-366 is not federally scheduled, although some states have passed legislation banning the sale, possession, and manufacture of JWH-366.[2][3][4][5]

In Canada, JWH-366 and other naphthoylpyrrole-based cannabinoids are Schedule II controlled substances under the Controlled Drugs and Substances Act.

In the United Kingdom, JWH-366 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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