O-823

O-823 is a drug which is a cannabinoid derivative that is used in scientific research. It is described as a mixed agonist/antagonist at the cannabinoid receptor CB1, meaning that it acts as an antagonist when co-administered alongside a more potent CB1 agonist, but exhibits weak partial agonist effects when administered by itself.[1][2][3]

O-823
Identifiers
IUPAC name
  • 7-[(6aR,10aR)-1-hydroxy-6,6,9-trimethyl-6a,7,10,10a-tetrahydrobenzo[c]chromen-3-yl]hept-5-ynenitrile
PubChem CID
ChemSpider
Chemical and physical data
FormulaC23H27NO2
Molar mass349.474 g·mol−1
3D model (JSmol)
SMILES
  • Oc2cc(CC#CCCCC#N)cc(OC1(C)C)c2C3C1CC=C(C)C3
InChI
  • InChI=1S/C23H27NO2/c1-16-10-11-19-18(13-16)22-20(25)14-17(9-7-5-4-6-8-12-24)15-21(22)26-23(19,2)3/h10,14-15,18-19,25H,4,6,8-9,11,13H2,1-3H3/t18-,19-/m1/s1 Y
  • Key:MZMMIGOIGWVGEH-RTBURBONSA-N Y
  (verify)

References
  1. Pertwee RG, Fernando SR, Griffin G, Ryan W, Razdan RK, Compton DR, Martin BR (November 1996). "Agonist-antagonist characterization of 6'-cyanohex-2'-yne-delta 8-tetrahydrocannabinol in two isolated tissue preparations". European Journal of Pharmacology. 315 (2): 195–201. doi:10.1016/s0014-2999(96)00631-0. PMID 8960884.
  2. Griffin G, Wray EJ, Rorrer WK, Crocker PJ, Ryan WJ, Saha B, et al. (April 1999). "An investigation into the structural determinants of cannabinoid receptor ligand efficacy". British Journal of Pharmacology. 126 (7): 1575–84. doi:10.1038/sj.bjp.0702469. PMC 1565939. PMID 10323589.
  3. Griffin G, Wray EJ, Martin BR, Abood ME (October 1999). "Cannabinoid agonists and antagonists discriminated by receptor binding in rat cerebellum". British Journal of Pharmacology. 128 (3): 684–8. doi:10.1038/sj.bjp.0702806. PMC 1571656. PMID 10516649.
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