JWH-363

JWH-363 (1-Naphthyl{1-pentyl-5-[3-(trifluoromethyl)phenyl]-1H-pyrrol-3-yl}methanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as an agonist of the CB₁ (K_i = 245 ± 5nM) and CB₂ (K_i = 71 ± 1nM) receptors, with a moderate (~3.45x) selectivity for the latter. JWH-363 was first synthesized in 2006 by John W. Huffman and colleagues to examine the nature of ligand binding to the CB₁ receptor.^[1]

JWH-363

Legal status
Legal status	CA: Schedule II UK: Class B
Identifiers
IUPAC name 1-Naphthyl{1-pentyl-5-[3-(trifluoromethyl)phenyl]-1H-pyrrol-3-yl}methanone
CAS Number	914458-33-6 Y
PubChem CID	44418338
ChemSpider	23277916 Y
CompTox Dashboard (EPA)	DTXSID701337009
Chemical and physical data
Formula	C27H24F3NO
Molar mass	435.490 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCCCCN1C=C(C=C1C2=CC(=CC=C2)C(F)(F)F)C(=O)C3=CC=CC4=CC=CC=C43
InChI InChI=1S/C27H24F3NO/c1-2-3-6-15-31-18-21(17-25(31)20-11-7-12-22(16-20)27(28,29)30)26(32)24-14-8-10-19-9-4-5-13-23(19)24/h4-5,7-14,16-18H,2-3,6,15H2,1H3 Y Key:GETLFVZYXNFVJS-UHFFFAOYSA-N Y

Legality

In the United States JWH-363 is not federally scheduled, although some states have passed legislation banning the sale, possession, and manufacture of JWH-363.^[2][3][4][5]

In Canada, JWH-363 and other naphthoylpyrrole-based cannabinoids are Schedule II controlled substances under the Controlled Drugs and Substances Act.

In the United Kingdom, JWH-363 and other naphthoylpyrrole-based cannabinoids are considered Class B drugs under the Misuse of Drugs Act 1971.

See also

• List of JWH cannabinoids
• Synthetic cannabinoid

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.