JWH-147

JWH-147
Legal status
Legal status
Identifiers
IUPAC name
  • (1-Hexyl-5-phenyl-1H-pyrrol-3-yl)-1-naphthalenyl-methanone
CAS Number
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC27H27NO
Molar mass381.519 g·mol−1
3D model (JSmol)
SMILES
  • c4ccccc4-c2cc(cn2CCCCCC)C(=O)c1cccc3c1cccc3
InChI
  • InChI=1S/C27H27NO/c1-2-3-4-10-18-28-20-23(19-26(28)22-13-6-5-7-14-22)27(29)25-17-11-15-21-12-8-9-16-24(21)25/h5-9,11-17,19-20H,2-4,10,18H2,1H3 ☒N
  • Key:FRMYAMAGHYHNKF-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

JWH-147 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 11.0 nM at CB1 vs 7.1 nM at CB2.[1] It was discovered and named after John W. Huffman.

In the United States, CB1 receptor agonists of the 3-(1-naphthoyl)pyrrole class such as JWH-147 are Schedule I Controlled Substances.[2]

JWH-147 was banned in Sweden on 1 October 2010 as harmful to health, after being identified as an ingredient in "herbal" synthetic cannabis products.[3][4]

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. ↑ Swedish Code of Statutes Regulation (2010:1086).
  4. ↑ "Swedish Code of Statutes Regulation (2010:1086). (pdf)" (PDF). Archived from the original (PDF) on 2011-07-28. Retrieved 2011-01-10.
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