Cannabicyclohexanol

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Cannabicyclohexanol
Cannabicyclohexanol.png
Systematic (IUPAC) name
2-[(1R,3S)-3-hydroxycyclohexyl]- 5-(2-methylnonan-2-yl)phenol
Clinical data
Legal status
  • Illegal in Germany and France, Class B (UK),United States: Schedule 1[1]
Identifiers
CAS number 70434-92-3 YesY
ATC code ?
PubChem CID 12788230
ChemSpider 26668381 N
Chemical data
Formula C22H36O2 
Mol. mass 332.519 g/mol
 N (what is this?)  (verify)

Cannabicyclohexanol (CCH, CP 47,497 dimethyloctyl homologue, (C8)-CP 47,497) is a cannabinoid receptor agonist drug, developed by Pfizer in 1979. On 19 January 2009, the University of Freiburg in Germany announced that an analog of CP 47,497 was the main active ingredient in the herbal incense product Spice, specifically the 1,1-dimethyloctyl homologue of CP 47,497, which is now known as cannabicyclohexanol.[2][3][4][5] The 1,1-dimethyloctyl homologue of CP 47,497 is in fact several times more potent than the parent compound,[6] which is somewhat unexpected as the 1,1-dimethylheptyl is the most potent substituent in classical cannabinoid compounds such as HU-210.[7]

See also[edit]

References[edit]

  1. ^ Cook, Morgan (2011-02-28). "Synthetic marijuana illegal as of Tuesday". North County Times (San Diego). Retrieved 2011-02-28. 
  2. ^ Hauptwirkstoff von „Spice“ identifiziert, University of Freiburg http://www.pr.uni-freiburg.de/pm/2009/pm.2009-01-19.19/
  3. ^ Spice - weitere Analyseresultate http://www.basg.at/servlet/sls/Tornado/web/ages/content/4E5A4B86295BF5C0C125753E006A5E3C
  4. ^ Auwärter V, et al. 'Spice' and other herbal blends: harmless incense or cannabinoid designer drugs? Journal of Mass Spectrometry. 2 February 2009. PMID 19189348
  5. ^ Uchiyama N, Kikura-Hanajiri R, Ogata J, Goda Y (May 2010). "Chemical analysis of synthetic cannabinoids as designer drugs in herbal products". Forensic Science International 198 (1-3): 31–8. doi:10.1016/j.forsciint.2010.01.004. PMID 20117892. 
  6. ^ Compton DR, Johnson MR, Melvin LS, Martin BR. Pharmacological profile of a series of bicyclic cannabinoid analogs: classification as cannabimimetic agents. Journal of Pharmacology and Experimental Therapeutics. 1992 Jan;260(1):201-9. PMID 1309872
  7. ^ Martin BR, et al. Behavioral, biochemical, and molecular modeling evaluations of cannabinoid analogs. Pharmacology, Biochemistry and Behavior. 1991 Nov;40(3):471-8. PMID 1666911