O-1871

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	620964-96-7 ;
PubChem CID	10405368;
ChemSpider	8580806;
UNII	SGY2L36FDU;
CompTox Dashboard (EPA)	DTXSID301045400 ;
Chemical and physical data
Formula	C23H38O2
Molar mass	346.555 g·mol−1
3D model (JSmol)	Interactive image;
	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.^[1] Structurally, O-1871 is a cyclohexylphenol derivative related to CP 47,497,^[2] 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,^[3] which are not cyclohexylphenol derivatives.

References

^ WO application 03091189, Martin BR, Razdan RK, "Cannabinoids", published 6 November 2003, assigned to University of Virginia
^ 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.
^ US application 2004087590, Lai XZ, Lu D, Makriyannis A, "Novel biphenyl and biphenyl-like cannabinoids", published 6 May 2004, assigned to University of Connecticut

[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

[1]

[2]

[3]

See also

References