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JWH-249

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
JWH-249
Legal status
Legal status
Identifiers
  • 2-(2-Bromophenyl)-1-(1-pentylindol-3-yl)ethanone
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC21H22BrNO
Molar mass384.317 g·mol−1
3D model (JSmol)
  • CCCCCn1cc(c2c1cccc2)C(=O)Cc3ccccc3Br
  • 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 checkY
  • Key:CGQRVOHECAULLB-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

JWH-249 (1-pentyl-3-(2-bromophenylacetyl)indole) is asynthetic cannabinoid from thephenylacetylindole family, which acts as acannabinoid agonist with about 2.4 times selectivity forCB1 with aKi of 8.4 ± 1.8 nM and 20 ± 2 nM atCB2. Similar to the related 2'-methoxy compoundJWH-250, the 2'-chloro compoundJWH-203, and the 2'-methyl compoundJWH-251, JWH-249 has aphenylacetyl group in place of thenaphthoyl ring used in mostaminoalkylindolecannabinoid compounds.[1][2]

In the United States, CB1 receptor agonists of the 3-phenylacetylindole class such as cannabipiperidiethanone areSchedule I Controlled Substances.[3]

See also

[edit]

References

[edit]
  1. ^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.
  2. ^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.
  3. ^21 U.S.C. § 812:Schedules of controlled substances
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