JWH-249

JWH-249

Legal status
Legal status	CA: Schedule II
Identifiers
IUPAC name 2-(2-bromophenyl)-1-(1-pentylindol-3-yl)ethanone
CAS Number	864445-60-3
PubChem (CID)	44397335
ChemSpider	23253217
ChEMBL	CHEMBL363471
Chemical and physical data
Formula	C21H22BrNO
Molar mass	384.31 g/mol
3D model (Jmol)	Interactive image
SMILES CCCCCn1cc(c2c1cccc2)C(=O)Cc3ccccc3Br
InChI InChI=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 Key:CGQRVOHECAULLB-UHFFFAOYSA-N
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JWH-249 (1-pentyl-3-(2-bromophenylacetyl)indole) is a synthetic cannabinoid from the phenylacetylindole family, which acts as a cannabinoid agonist with about 2.4x selectivity for CB₁ with a K_i of 8.4nM ± 1.8 and 20nM ± 2 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]

See also

• AM-679

References

1. Huffman JW, Szklennik PV, Almond A, Bushell K, Selley DE, He H, Cassidy MP, Wiley JL, Martin BR (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.
2. Manera C, Tuccinardi T, Martinelli A (2008). "Indoles and related compounds as cannabinoid ligands". Mini reviews in medicinal chemistry. 8 (4): 370–87. doi:10.2174/138955708783955935. PMID 18473928.