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;
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, 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.
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 & Medicinal Chemistry. 2005; 13:89-112.
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.
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.

[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 & 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.

[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