JWH-145

JWH-145 (1-naphthalenyl(1-pentyl-5-phenyl-1H-pyrrol-3-yl)-methanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as an agonist of the CB1 (Ki = 14 ± 2nM) and CB2 (Ki = 6.4 ± 0.4nM) receptors, with a moderate (~2.2x) selectivity for the CB2 receptor. JWH-145 was first synthesized in 2006 by John W. Huffman and colleagues to examine the nature of ligand binding to the CB1 receptor.[1]

JWH-145
Legal status
Legal status
Identifiers
IUPAC name
  • 1-naphthalenyl(1-pentyl-5-phenyl-1H-pyrrol-3-yl)-methanone
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC26H25NO
Molar mass367.492 g·mol−1
3D model (JSmol)
SMILES
  • O=C(C1=CN(CCCCC)C(C2=CC=CC=C2)=C1)C3=C(C=CC=C4)C4=CC=C3
InChI
  • InChI=1S/C26H25NO/c1-2-3-9-17-27-19-22(18-25(27)21-12-5-4-6-13-21)26(28)24-16-10-14-20-11-7-8-15-23(20)24/h4-8,10-16,18-19H,2-3,9,17H2,1H3 Y
  • Key:JLXYYSHMURZHKI-UHFFFAOYSA-N Y

Legality

In the United States JWH-145 is not federally scheduled, although some states have passed legislation banning the sale, possession, and manufacture of JWH-145.[2][3][4][5]

In Canada, JWH-145 and other naphthoylpyrrole-based cannabinoids are Schedule II controlled substances under the Controlled Drugs and Substances Act.

In the United Kingdom, JWH-145 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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