JWH-250

JWH-250
Legal status
Legal status
Identifiers
  • 2-(2-Methoxyphenyl)-1-(1-pentylindol-3-yl)ethanone
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC22H25NO2
Molar mass335.447 g·mol−1
3D model (JSmol)
  • COc2ccccc2CC(=O)c(c3ccccc13)cn1CCCCC
  • InChI=1S/C22H25NO2/c1-3-4-9-14-23-16-19(18-11-6-7-12-20(18)23)21(24)15-17-10-5-8-13-22(17)25-2/h5-8,10-13,16H,3-4,9,14-15H2,1-2H3 ☒N
  • Key:FFLSJIQJQKDDCM-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

JWH-250 or (1-pentyl-3-(2-methoxyphenylacetyl)indole) is an analgesic chemical from the phenylacetylindole family that acts as a cannabinoid agonist at both the CB1 and CB2 receptors, with a Ki of 11 nM at CB1 and 33 nM at CB2. Unlike many of the older JWH series compounds, this compound does not have a naphthalene ring, instead occupying this position with a 2'-methoxy-phenylacetyl group, making JWH-250 a representative member of a new class of cannabinoid ligands.[4] Other 2'-substituted analogues such as the methyl, chloro and bromo compounds are also active and somewhat more potent.[5][6]

History

JWH-250 was discovered by, and named after the researcher John W. Huffman. He created JWH-250 and a number of other compounds to research the structure and function of the endocannabinoid system of mammals. Samples of JWH-250 were first identified in May 2009 by the German Federal Criminal Police, as an ingredient in new generation "herbal smoking blends" that had been released since the banning of the original ingredients (C8)-CP 47,497 and JWH-018.[7] An ELISA immunoassay technique for detecting JWH-250 in urine has been reported.[8]

Australia

JWH-250 is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015).[9] A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities.[9]

United States

In the United States, CB1 receptor agonists of the 3-phenylacetylindole class such as JWH-250 are Schedule I Controlled Substances.[10]

See also

References

  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. ^ Legal article in Latvian (www.likumi.lv)
  4. ^ Huffman JW, Szklennik PV, Almond A, Bushell K, Selley DE, He H, et al. (September 2005). "1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles". Bioorganic & Medicinal Chemistry Letters. 15 (18): 4110–3. doi:10.1016/j.bmcl.2005.06.008. PMID 16005223.
  5. ^ Manera C, Tuccinardi T, Martinelli A (April 2008). "Indoles and related compounds as cannabinoid ligands". Mini Reviews in Medicinal Chemistry. 8 (4): 370–87. doi:10.2174/138955708783955935. PMID 18473928.
  6. ^ The Cannabinoid Receptors. Edited by Patricia H Reggio. Humana Press 2009. ISBN 978-1-58829-712-9
  7. ^ "Understanding the 'Spice' phenomenon. EMCDDA, Lisbon, November 2009" (PDF). Archived from the original (PDF) on 2010-04-08. Retrieved 2009-11-05.
  8. ^ Arntson A, Ofsa B, Lancaster D, Simon JR, McMullin M, Logan B (June 2013). "Validation of a novel immunoassay for the detection of synthetic cannabinoids and metabolites in urine specimens". Journal of Analytical Toxicology. 37 (5): 284–90. doi:10.1093/jat/bkt024. PMID 23625703.
  9. ^ a b Poisons Standard October 2015 https://www.comlaw.gov.au/Details/F2015L01534
  10. ^ 21 U.S.C. § 812: Schedules of controlled substances
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