JWH-081

JWH-081
Legal status
Legal status	CA: Schedule II ; DE: Anlage II (Authorized trade only, not prescriptible) ; UK: Under Psychoactive Substances Act ; US: Schedule I ; I-N (Poland)[1];
Identifiers
	IUPAC name 4-Methoxynaphthalen-1-yl-(1-pentylindol-3-yl)methanone;
CAS Number	210179-46-7 ;
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.[2] With a K_i 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 John W. Huffman.

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

Legal status

In the United States, JWH-081 is a Schedule I Controlled Substance.[5]

As of October 2015, JWH-081 is a controlled substance in China.[6]

References

"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.
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.
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.
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.
Controlled Substances listed by the DEA
"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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[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.

[pmid10940540-2] 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.

[pmid15582455-3] 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.

[4] 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.

[5] Controlled Substances listed by the DEA

[6] "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.

JWH-081

Legal status

See also

References