JWH-359

JWH-359
Identifiers
  • (6aR,10aR)- 1-Methoxy- 6,6,9-trimethyl- 3-[(2R)-1,1,2-trimethylbutyl]- 6a,7,10,10a-tetrahydrobenzo[c]chromene
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC24H36O2
Molar mass356.550 g·mol−1
3D model (JSmol)
  • C[C@H](CC)C(C)(C)c1cc2OC(C)(C)[C@@H]3CC=C(C)C[C@H]3c2c(OC)c1
  • 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.[1][2] 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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