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O-1871

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Chemical compound Pharmaceutical compound
O-1871
Clinical data
ATC code
  • none
Legal status
Legal status
  • Banned as cyclohexylphenol derivative (US, UK)
Identifiers
IUPAC name
  • 2-(3,3-dimethylcyclohexyl)-5-(2-methyloctan-2-yl)benzene-1,3-diol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H38O2
Molar mass346.555 g·mol
3D model (JSmol)
SMILES
  • CC(C1)(C)CCCC1C2=C(O)C=C(C(C)(C)CCCCCC)C=C2O
InChI
  • InChI=1S/C23H38O2/c1-6-7-8-9-13-23(4,5)18-14-19(24)21(20(25)15-18)17-11-10-12-22(2,3)16-17/h14-15,17,24-25H,6-13,16H2,1-5H3
  • Key:WBSPBIRKSHKQQD-UHFFFAOYSA-N

O-1871 is a potent cannabinoid agonist which was invented by Billy R Martin and Raj K Razdan at Organix Inc in 2002. It has a CB1 receptor affinity of 2.0 nM and a CB2 receptor affinity of 0.3 nM. Structurally, O-1871 is a cyclohexylphenol derivative related to CP 47,497, and so is illegal in some jurisdictions where CP 47,497 and its derivatives are banned. However the 3,3-dimethylcyclohexyl substituent of O-1871 can be replaced by various other groups, producing other potent compounds such as the cycloheptyl derivative O-1656 and the 2-adamantyl derivative O-1660, as well as the corresponding 3,5-dichlorophenyl derivative, which are not cyclohexylphenol derivatives.

O-1656, CAS# 468083-75-2
O-1660,

See also

References

  1. WO application 03091189, Martin BR, Razdan RK, "Cannabinoids", published 6 November 2003, assigned to University of Virginia 
  2. Debruyne D, Le Boisselier R (2015). "Emerging drugs of abuse: current perspectives on synthetic cannabinoids". Substance Abuse and Rehabilitation. 6: 113–29. doi:10.2147/SAR.S73586. PMC 4622447. PMID 26543389.
  3. US application 2004087590, Lai XZ, Lu D, Makriyannis A, "Novel biphenyl and biphenyl-like cannabinoids", published 6 May 2004, assigned to University of Connecticut 
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