JWH-210

JWH-210
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics); CA: Schedule II; DE: Anlage II; UK: Class B; US: Schedule I; Illegal in Sweden, I-N (Poland);
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 ;
	(what is this?) (verify)

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).^[4] It was discovered by and named after John W. Huffman.

JWH-210 may be neurotoxic to animals when administered in high doses.^[5]

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.^[6]

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.^[7]^[8] The substances JWH-210, JWH-122 and JWH-203 were classified as illegal drugs by the Swedish government as of 1 September 2011.^[9]

As of October 2015 JWH-210 is a controlled substance in China.^[10]

References

^ "Stoffe gem. Anlagen zum BtMG". Retrieved 2024-11-23.
^ 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.
^ "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. Archived from the original on 1 October 2015. Retrieved 1 October 2015.

[1] "Stoffe gem. Anlagen zum BtMG". Retrieved 2024-11-23.

[2] 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.

[3] "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.

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

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

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

[9] LVFS 2011:8

[10] "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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Legal status

See also

References