JWH-302

JWH-302
Legal status
Legal status
Identifiers
IUPAC name
  • 2-(3-Methoxyphenyl)-1-(1-pentylindol-3-yl)ethanone
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC22H25NO2
Molar mass335.447 g·mol−1
3D model (JSmol)
SMILES
  • c2ccc(OC)cc2CC(=O)c(cn1CCCCC)c3ccccc13
InChI
  • InChI=1S/C22H25NO2/c1-3-4-7-13-23-16-20(19-11-5-6-12-21(19)23)22(24)15-17-9-8-10-18(14-17)25-2/h5-6,8-12,14,16H,3-4,7,13,15H2,1-2H3 checkY
  • Key:XZVYWLVYUAQEIM-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

JWH-302 (1-pentyl-3-(3-methoxyphenylacetyl)indole) is an analgesic chemical from the phenylacetylindole family, which acts as a cannabinoid agonist with moderate affinity at both the CB1 and CB2 receptors. It is a positional isomer of the more common drug JWH-250, though it is slightly less potent with a Ki of 17 nM at CB1, compared to 11 nM for JWH-250.[1][2] Because of their identical molecular weight and similar fragmentation patterns, JWH-302 and JWH-250 can be very difficult to distinguish by GC-MS testing.[3]

In the United States, CB1 receptor agonists of the 3-phenylacetylindole class such as JWH-302 are Schedule I Controlled Substances.[4]

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. ↑ 'Herbal High' synthetic Cannabinoid composition, released by ESR July 2011
  4. ↑ 21 U.S.C. § 812: Schedules of controlled substances
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