JWH-307

JWH-307
Legal status
Legal status
  • DE: Anlage II (Authorized trade only, not prescriptible)
  • US: Schedule I
Identifiers
IUPAC name
  • (5-(2-Fluorophenyl)-1-pentylpyrrol-3-yl)-naphthalen-1-ylmethanone
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC26H24FNO
Molar mass385.482 g·mol−1
3D model (JSmol)
SMILES
  • CCCCCN1C=C(C=C1C2=CC=CC=C2F)C(=O)C3=CC=CC4=CC=CC=C43
InChI
  • InChI=1S/C26H24FNO/c1-2-3-8-16-28-18-20(17-25(28)23-13-6-7-15-24(23)27)26(29)22-14-9-11-19-10-4-5-12-21(19)22/h4-7,9-15,17-18H,2-3,8,16H2,1H3
  • Key:WYNZPDDTQGVCLZ-UHFFFAOYSA-N
  (verify)

JWH-307 is an analgesic drug used in scientific research, which acts as a cannabinoid agonist at both the CB1 and CB2 receptors. It is somewhat selective for the CB2 subtype, with a Ki of 7.7 nM at CB1 vs 3.3 nM at CB2.[1] It was discovered by, and named after, John W. Huffman. JWH-307 was detected as an ingredient in synthetic cannabis smoking blends in 2012, initially in Germany.[2][3]

In the United States, CB1 receptor agonists of the 3-(1-naphthoyl)pyrrole class such as JWH-307 are Schedule I Controlled Substances.[4]

See also

References

  1. ↑ Huffman JW, Padgett LW, Isherwood ML, Wiley JL, Martin BR. 1-Alkyl-2-aryl-4-(1-naphthoyl)pyrroles: New high affinity ligands for the cannabinoid CB1 and CB2 receptors. Bioorganic & Medicinal Chemistry Letters 2006; 16:5432-5435.
  2. ↑ Ernst L, Krüger K, Lindigkeit R, Schiebel HM, Beuerle T (October 2012). "Synthetic cannabinoids in "spice-like" herbal blends: first appearance of JWH-307 and recurrence of JWH-018 on the German market". Forensic Science International. 222 (1–3): 216–22. doi:10.1016/j.forsciint.2012.05.027. PMID 22748479.
  3. ↑ Kneisel S, Auwärter V (July 2012). "Analysis of 30 synthetic cannabinoids in serum by liquid chromatography-electrospray ionization tandem mass spectrometry after liquid-liquid extraction". Journal of Mass Spectrometry. 47 (7): 825–35. Bibcode:2012JMSp...47..825K. doi:10.1002/jms.3020. PMID 22791249.
  4. ↑ 21 U.S.C. § 812: Schedules of controlled substances
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