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JWH-372

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Chemical compound Pharmaceutical compound
JWH-372
Legal status
Legal status
Identifiers
IUPAC name
  • naphthalen-1-yl-pyrrol-3-yl]methanone
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC27H24F3NO
Molar mass435.490 g·mol
3D model (JSmol)
SMILES
  • CCCCCN1C=C(C=C1C2=CC=CC=C2C(F)(F)F)C(=O)C3=CC=CC4=CC=CC=C43
InChI
  • InChI=1S/C27H24F3NO/c1-2-3-8-16-31-18-20(17-25(31)23-13-6-7-15-24(23)27(28,29)30)26(32)22-14-9-11-19-10-4-5-12-21(19)22/h4-7,9-15,17-18H,2-3,8,16H2,1H3
  • Key:CYPUIQJYGVOHMM-UHFFFAOYSA-N

JWH-372 (naphthalen-1-yl-pyrrol-3-yl]methanone) is a synthetic cannabinoid from the naphthoylpyrrole family which acts as a potent and selective agonist of the CB2 receptor. JWH-372 binds approximately 9 times stronger to the CB2 receptor (Ki = 8.2 ± 0.2nM) than the CB1 receptor (Ki = 77 ± 2nM). The selectivity of JWH-372 for the CB2 receptor is likely due to the electron-withdrawing character of the trifluoromethyl group rather than steric effects, as the o-methyl compound JWH-370 was only mildly selective for the CB2 receptor (CB1 Ki = 5.6 ± 0.4nM, CB2 Ki = 4.0 ± 0.5nM).

Legality

In the United States JWH-372 is not federally scheduled, although some states have passed legislation banning the sale, possession, and manufacture of JWH-372.

In Canada, JWH-372 and other naphthoylpyrrole-based cannabinoids are Schedule II controlled substances under the Controlled Drugs and Substances Act.

In the United Kingdom, JWH-372 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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