JWH-081

JWH-081

Legal status
Legal status	BR: Class F2 (Prohibited psychotropics) [1] CA: Schedule II DE: Anlage II (Authorized trade only, not prescriptible) UK: Class B US: Schedule I I-N (Poland) [2]
Identifiers
IUPAC name 4-Methoxynaphthalen-1-yl-(1-pentylindol-3-yl)methanone
CAS Number	210179-46-7  Y
PubChem CID	10547208
ChemSpider	8722599
UNII	77E58024IT
CompTox Dashboard (EPA)	DTXSID80175225
ECHA InfoCard	100.230.181
Chemical and physical data
Formula	C25H25NO2
Molar mass	371.480 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCCCCn3c1ccccc1c(c3)C(=O)c4c2ccccc2c(OC)cc4
InChI 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 K_i 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]

Legal status

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

• JWH-018
• JWH-098
• JWH-164
• JWH-198
• JWH-210

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.