JWH-081
Legal status
Legal status
Identifiers
  • 4-Methoxynaphthalen-1-yl-(1-pentylindol-3-yl)methanone
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.230.181
Chemical and physical data
FormulaC25H25NO2
Molar mass371.480 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.[3] With a Ki of 1.2nM it is fairly selective for the CB1 subtype, its affinity at this subtype is measured at approximately 10x the affinity at CB2(12.4nM).[4] It was discovered by and named after John W. Huffman.

JWH-081 may be neurotoxic to animals when administered in high doses.[5]

In the United States, JWH-081 is a Schedule I Controlled Substance.[6]

As of October 2015, JWH-081 is a controlled substance in China.[7]

See also

References

  1. ↑ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  2. ↑ "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.
  3. ↑ Aung MM, Griffin G, Huffman JW, Wu M, Keel C, Yang B, et al. (August 2000). "Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB(1) and CB(2) receptor binding". Drug and Alcohol Dependence. 60 (2): 133–40. doi:10.1016/s0376-8716(99)00152-0. PMID 10940540.
  4. ↑ Huffman JW, Zengin G, Wu MJ, Lu J, Hynd G, Bushell K, et al. (January 2005). "Structure-activity relationships for 1-alkyl-3-(1-naphthoyl)indoles at the cannabinoid CB(1) and CB(2) receptors: steric and electronic effects of naphthoyl substituents. New highly selective CB(2) receptor agonists". Bioorganic & Medicinal Chemistry. 13 (1): 89–112. doi:10.1016/j.bmc.2004.09.050. PMID 15582455.
  5. ↑ Cha HJ, Seong YH, Song MJ, Jeong HS, Shin J, Yun J, et al. (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.
  6. ↑ Controlled Substances listed by the DEA
  7. ↑ "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. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
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