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JWH-359

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Chemical compound Pharmaceutical compound
JWH-359
Identifiers
IUPAC name
  • (6aR,10aR)- 1-Methoxy- 6,6,9-trimethyl- 3-- 6a,7,10,10a-tetrahydrobenzochromene
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC24H36O2
Molar mass356.550 g·mol
3D model (JSmol)
SMILES
  • C(CC)C(C)(C)c1cc2OC(C)(C)3CC=C(C)C3c2c(OC)c1
InChI
  • InChI=1S/C24H36O2/c1-9-16(3)23(4,5)17-13-20(25-8)22-18-12-15(2)10-11-19(18)24(6,7)26-21(22)14-17/h10,13-14,16,18-19H,9,11-12H2,1-8H3/t16-,18-,19-/m1/s1
  • Key:BDJRWUBZMGSKHL-BHIYHBOVSA-N
  (verify)

JWH-359 is a dibenzopyran "classical" cannabinoid drug, which is a potent and selective CB2 receptor agonist, with a Ki of 13.0 nM and selectivity of around 220 times for CB2 over CB1 receptors. It is related to other dibenzopyran CB2 agonists such as JWH-133 and L-759,656 but with a chiral side chain which has made it useful for mapping the shape of the CB2 binding site. It was discovered by, and named after, John W. Huffman.

References

  1. Huffman JW, Bushell SM, Joshi SN, Wiley JL, Martin BR (January 2006). "Enantioselective synthesis of 1-methoxy- and 1-deoxy-2'-methyl-delta8-tetrahydrocannabinols: new selective ligands for the CB2 receptor". Bioorganic & Medicinal Chemistry. 14 (1): 247–62. doi:10.1016/j.bmc.2005.08.013. PMID 16165365.
  2. Marriott KS, Huffman JW (2008). "Recent advances in the development of selective ligands for the cannabinoid CB(2) receptor". Current Topics in Medicinal Chemistry. 8 (3): 187–204. doi:10.2174/156802608783498014. PMID 18289088.
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