JWH-210

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 Ki 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 Ki) at CB1 than both its 4-methyl and 4-n-propyl homologues JWH-122 (CB1 Ki 0.69 nM) and JWH-182 (CB1 Ki 0.65 nM) respectively, and than the 4-methoxy compound JWH-081 (CB1 Ki 1.2 nM).[3] It was discovered by and named after John W. Huffman.

JWH-210
Legal status
Legal status
Identifiers
  • 4-Ethylnaphthalen-1-yl-(1-pentylindol-3-yl)methanone
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.233.380
Chemical and physical data
FormulaC26H27NO
Molar mass369.508 g·mol−1
3D model (JSmol)
  • c4cccc2c4c(CC)ccc2C(=O)c(c3)c1ccccc1n3CCCCC
  • 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 ☒N
  • Key:LACIUQLUNACUKC-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

JWH-210 may be neurotoxic to animals when administered in high doses.[4]

In the United States, all CB1 receptor agonists of the 3-(1-naphthoyl)indole class such as JWH-210 are Schedule I Controlled Substances.[5]

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.[6][7] The substances JWH-210, JWH-122 and JWH-203 were classified as illegal drugs by the Swedish government as of 1 September 2011.[8]

As of October 2015 JWH-210 is a controlled substance in China.[9]

See also

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. 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. 21 U.S.C. § 812: Schedules of controlled substances
  6. Swedish Code of Statutes Regulation (2010:1086).
  7. "Swedish Code of Statutes Regulation (2010:1086). (pdf)" (PDF). Archived from the original (PDF) on 2011-07-28. Retrieved 2011-01-10.
  8. LVFS 2011:8
  9. "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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