JWH-251
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| Preferred IUPAC name
2-(2-Methylphenyl)-1-(1-pentyl-1H-indol-3-yl)ethan-1-one | |
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3D model (JSmol)
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C22H25NO | |
| Molar mass | 319.448 g·mol−1 |
| Pharmacology | |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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JWH-251 (1-pentyl-3-(2-methylphenylacetyl)indole) is a synthetic cannabinoid from the phenylacetylindole family, which acts as a cannabinoid agonist with about five times selectivity for CB1 with a Ki of 29 nM and 146 nM at CB2. Similar to the related 2'-methoxy compound JWH-250, the 2'-chloro compound JWH-203, and the 2'-bromo compound JWH-249, JWH-251 has a phenylacetyl group in place of the naphthoyl ring used in most aminoalkylindole cannabinoid compounds.[3][4]
In the United States, all CB1 receptor agonists of the 3-phenylacetylindole class such as JWH-251 are Schedule I Controlled Substances.[5]
References
[edit]- ^ "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.
- ^ 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.
- ^ 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.
- ^ : Schedules of controlled substances
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