Cannabis Ruderalis

JWH-081
Legal status
Legal status
  • DE: Anlage II (Authorized trade only, not prescriptible)
  • I-N (Poland)[1]
Identifiers
  • 4-methoxynaphthalen- 1-yl- (1-pentylindol- 3-yl)methanone
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
ECHA InfoCard100.230.181 Edit this at Wikidata
Chemical and physical data
FormulaC25H25NO2
Molar mass371.47 g/mol g·mol−1
3D model (JSmol)
  • CCCCCn3c1ccccc1c(c3)C(=O)c4c2ccccc2c(OC)cc4
  • InChI=1S/C25H25NO2/c1-3-4-9-16-26-17-22(19-11-7-8-13-23(19)26)25(27)21-14-15-24(28-2)20-12-6-5-10-18(20)21/h5-8,10-15,17H,3-4,9,16H2,1-2H3
  • Key:UBMPKJKGUQDHRM-UHFFFAOYSA-N
  (verify)

JWH-081 is an analgesic chemical from the naphthoylindole family, which acts as a cannabinoid agonist at both the CB1 and CB2 receptors.[2] With a Ki of 1.2nM it is fairly selective for the CB1 subtype, its affinity at this subtype approximately 10x the affinity at CB2.[3] It was discovered by and named after Dr. John W. Huffman.

JWH-081 may be neurotoxic to animals when administered in high doses.[4]

Legal Status

As of October 2015 JWH-081 is a controlled substance in China.[5]

See also

References

  1. ^ "Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii (Dz.U. 2011 nr 105 poz. 614)". Internetowy System Aktów Prawnych. Retrieved 12 June 2011.
  2. ^ Aung MM, et al. Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding. Drug and Alcohol Dependence 2000; 60:133-140.
  3. ^ Huffman JW, et al. Structure–activity relationships for 1-alkyl-3-(1-naphthoyl)indoles at the cannabinoid CB1 and CB2 receptors: steric and electronic effects of naphthoyl substituents. New highly selective CB2 receptor agonists. Bioorganic and Medicinal Chemistry. 2005; 13:89-112.
  4. ^ Hye Jin Cha, Yeon-Hee Seong, Min-Ji Song, Ho-Sang Jeong, Jisoon Shin, Jaesuk Yun, Kyoungmoon Han, Young-Hoon Kim, Hoil Kang, Hyoung Soo Kim (November 2015). "Neurotoxicity of Synthetic Cannabinoids JWH-081 and JWH-210". Biomolecules & Therapeutics. 23 (6): 597–603. doi:10.4062/biomolther.2015.057. PMC 4624077. PMID 26535086.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  5. ^ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Retrieved 1 October 2015.

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