| Verifiedfields | changed |
|---|---|
| Verifiedrevid | 477496189 |
| Iupac name | 2-(2-Bromophenyl)-1-(1-pentylindol-3-yl)ethanone |
| Width | 150 |
| Legal ca | Schedule II |
| Legal de | NpSG |
| Legal uk | PSA |
| Legal us | Schedule I |
| Cas number | 864445-60-3 |
| Unii | H988KQV4U9 |
| Chembl | 363471 |
| Pubchem | 44397335 |
| Chemspiderid | 23253217 |
| C | 21 |
| H | 22 |
| Br | 1 |
| N | 1 |
| O | 1 |
| Smiles | CCCCCn1cc(c2c1cccc2)C(=O)Cc3ccccc3Br |
| Stdinchi | 1S/C21H22BrNO/c1-2-3-8-13-23-15-18(17-10-5-7-12-20(17)23)21(24)14-16-9-4-6-11-19(16)22/h4-7,9-12,15H,2-3,8,13-14H2,1H3 |
| Stdinchikey | CGQRVOHECAULLB-UHFFFAOYSA-N |
JWH-249 (1-pentyl-3-(2-bromophenylacetyl)indole) is a synthetic cannabinoid from the phenylacetylindole family, which acts as a cannabinoid agonist with about 2.4 times selectivity for CB1 with a Ki of 8.4 ± 1.8 nM and 20 ± 2 nM at CB2. Similar to the related 2'-methoxy compound JWH-250, the 2'-chloro compound JWH-203, and the 2'-methyl compound JWH-251, JWH-249 has a phenylacetyl group in place of the naphthoyl ring used in most aminoalkylindole cannabinoid compounds.[1][2]
In the United States, CB1 receptor agonists of the 3-phenylacetylindole class such as cannabipiperidiethanone are Schedule I Controlled Substances.[3]
See also
References
- ^ Huffman JW, Szklennik PV, Almond A, Bushell K, Selley DE, He H, Cassidy MP, Wiley JL, Martin BR (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
- ^