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JWH-167

JWH-167
Names
Preferred IUPAC name
1-(1-Pentyl-1H-indol-3-yl)-2-phenylethan-1-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C21H23NO/c1-2-3-9-14-22-16-19(18-12-7-8-13-20(18)22)21(23)15-17-10-5-4-6-11-17/h4-8,10-13,16H,2-3,9,14-15H2,1H3 checkY
    Key: AMCPOEOUXQWESI-UHFFFAOYSA-N checkY
  • CCCCCn1cc(c2c1cccc2)C(=O)Cc3ccccc3
Properties
C21H23NO
Molar mass 305.421 g·mol−1
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-167 (1-pentyl-3-(phenylacetyl)indole) is a synthetic cannabinoid from the phenylacetylindole family, which acts as a cannabinoid agonist with about 1.75 times selectivity for CB1 with a Ki of 90 nM ± 17 and 159 nM ± 14 at CB2. Similar to the related 2'-methoxy compound JWH-250, and the 2'-chloro compound JWH-203, JWH-167 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 JWH-167 are Schedule I Controlled Substances.[3]

References

  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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