JWH-210

JWH-210
Legal status
Legal status	CA: Schedule II ; DE: Anlage II (Authorized trade only, not prescriptible) ; UK: Under Psychoactive Substances Act ; Illegal in Sweden, I-N(Poland)[1];
Identifiers
	IUPAC name 4-Ethylnaphthalen-1-yl-(1-pentylindol-3-yl)methanone;
CAS Number	824959-81-1 (JWH-210); 824960-02-3 (JWH-182);
PubChem CID	45270396;
ChemSpider	24617616 ;
UNII	R18JYO04PY;
CompTox Dashboard (EPA)	DTXSID301010019 ;
ECHA InfoCard	100.233.380
Chemical and physical data
Formula	C26H27NO
Molar mass	369.508 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES c4cccc2c4c(CC)ccc2C(=O)c(c3)c1ccccc1n3CCCCC;
	InChI InChI=1S/C26H27NO/c1-3-5-10-17-27-18-24(22-13-8-9-14-25(22)27)26(28)23-16-15-19(4-2)20-11-6-7-12-21(20)23/h6-9,11-16,18H,3-5,10,17H2,1-2H3 ; Key:LACIUQLUNACUKC-UHFFFAOYSA-N ;
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JWH-210 is an analgesic chemical from the naphthoylindole family, which acts as a potent cannabinoid agonist at both the CB₁ and CB₂ receptors, with K_i values of 0.46 nM at CB₁ and 0.69 nM at CB₂. It is one of the most potent 4-substituted naphthoyl derivatives in the naphthoylindole series, having a higher binding affinity (i.e. lower K_i) at CB₁ than both its 4-methyl and 4-n-propyl homologues JWH-122 (CB₁ K_i 0.69 nM) and JWH-182 (CB₁ K_i 0.65 nM) respectively, and than the 4-methoxy compound JWH-081 (CB₁ K_i 1.2 nM).[2] It was discovered by and named after John W. Huffman.

JWH-210 may be neurotoxic to animals when administered in high doses.[3]

Legal status

In the United States, all CB₁ receptor agonists of the 3-(1-naphthoyl)indole class such as JWH-210 are Schedule I Controlled Substances.[4]

JWH-210 and JWH-122 were banned in Sweden on 1 October 2010 as hazardous goods harmful to health, after being identified as ingredients in "herbal" synthetic cannabis products.[5][6] The substances JWH-210, JWH-122 and JWH-203 were classified as illegal drugs by the Swedish government as of 1 September 2011.[7]

As of October 2015 JWH-210 is a controlled substance in China.[8]

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.
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.
21 U.S.C. § 812: Schedules of controlled substances
Swedish Code of Statutes Regulation (2010:1086).
"Swedish Code of Statutes Regulation (2010:1086). (pdf)" (PDF). Archived from the original (PDF) on 2011-07-28. Retrieved 2011-01-10.
LVFS 2011:8
"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] 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.

[3] 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.

[4] 21 U.S.C. § 812: Schedules of controlled substances

[5] Swedish Code of Statutes Regulation (2010:1086).

[6] "Swedish Code of Statutes Regulation (2010:1086). (pdf)" (PDF). Archived from the original (PDF) on 2011-07-28. Retrieved 2011-01-10.

[7] LVFS 2011:8

[8] "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-210

Legal status

See also

References