JWH-364

JWH-364 ([5-(4-Ethylphenyl)-1-pentyl-1H-pyrrol-3-yl](1-naphthyl)methanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as an agonist of the CB₁ (K_i = 34 ± 3nM) and CB₂ (K_i = 29 ± 1nM) receptors, with a slight selectivity for the latter. JWH-364 was first synthesized in 2006 by John W. Huffman and colleagues to examine the nature of ligand binding to the CB₁ receptor.^[1]

JWH-364

Legal status
Legal status	CA: Schedule II UK: Class B
Identifiers
IUPAC name [5-(4-Ethylphenyl)-1-pentyl-1H-pyrrol-3-yl](1-naphthyl)methanone
CAS Number	914458-36-9 Y
PubChem CID	44418348
ChemSpider	23277926 Y
CompTox Dashboard (EPA)	DTXSID001337008
Chemical and physical data
Formula	C28H29NO
Molar mass	395.546 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCCCCN1C=C(C=C1C2=CC=C(C=C2)CC)C(=O)C3=CC=CC4=CC=CC=C43
InChI InChI=1S/C28H29NO/c1-3-5-8-18-29-20-24(19-27(29)23-16-14-21(4-2)15-17-23)28(30)26-13-9-11-22-10-6-7-12-25(22)26/h6-7,9-17,19-20H,3-5,8,18H2,1-2H3 Y Key:VJWBAPGRMUZBEH-UHFFFAOYSA-N Y

Legality

In the United States JWH-364 is not federally scheduled, although some states have passed legislation banning the sale, possession, and manufacture of JWH-364.^[2][3][4][5]

In Canada, JWH-364 and other naphthoylpyrrole-based cannabinoids are Schedule II controlled substances under the Controlled Drugs and Substances Act.

In the United Kingdom, JWH-364 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.