Cannabicyclohexanol Explained

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.[1] [2] [3] The 1,1-dimethyloctyl homologue of CP 47,497 is in fact several times more potent than the parent compound,[4] which is somewhat unexpected as the 1,1-dimethylheptyl is the most potent substituent in classical cannabinoid compounds such as HU-210.[5]

Enantiomers

Cannabicyclohexanol has four enantiomers, which by analogy with other related cannabinoid compounds can be expected to have widely varying affinity for cannabinoid receptors, and consequently will show considerable variation in potency.[6] [7] While the (-)-cis enantiomer (-)-cannabicyclohexanol discovered in the original Pfizer research is expected to be the most potent, all four enantiomers have been isolated from illicit samples of this compound, and the properties of the other three enantiomers have not been studied in detail. Most commonly cannabicyclohexanol is encountered as a diastereomeric mix of the two cis or two trans isomers in varying ratios, though more rarely a mixture of all four enantiomers has been seen, as well as reasonably enantiopure samples of the most active isomer.[8] [9] [10] Confusion can arise around the naming of these compounds as they can be viewed either as substituted phenols or substituted cyclohexanols, but this results in different numbering of the rings. Consequently, the active isomer can be named either 2-[(1S,3R)-3-hydroxycyclohexyl]-5-(2-methylnonan-2-yl)phenol or (1R,3S)-3-[2-hydroxy-4-(2-methylnonan-2-yl)phenyl]cyclohexan-1-ol.

Toxicity

(C8)-CP 47,497 has been shown to cause DNA damage and inflammation in directly exposed human cells in vitro,[11] though it is unclear if this has any relevance in vivo.

Legal status

Cannabicyclohexanol is not listed in the schedules set out by the United Nations' Single Convention on Narcotic Drugs from 1961 nor their Convention on Psychotropic Substances from 1971,[12] so the signatory countries to these international drug control treaties are not required by said treaties to control Cannabicyclohexanol.

United States

Cannabicyclohexanol is a Schedule I controlled substance in the USA.[13]

Vermont

Effective January 1, 2016, cannabicyclohexanol is a regulated drug in Vermont designated as a "Hallucinogenic Drug."[14]

See also

Notes and References

  1. Web site: Hauptwirkstoff von "Spice" identifiziert . University of Freiburg . 19 March 2009 . 25 July 2015.
  2. Auwärter V, Dresen S, Weinmann W, Müller M, Pütz M, Ferreirós N . 'Spice' and other herbal blends: harmless incense or cannabinoid designer drugs? . Journal of Mass Spectrometry . 44 . 5 . 832–837 . May 2009 . 19189348 . 10.1002/jms.1558 . 2009JMSp...44..832A .
  3. Uchiyama N, Kikura-Hanajiri R, Ogata J, Goda Y . Chemical analysis of synthetic cannabinoids as designer drugs in herbal products . Forensic Science International . 198 . 1–3 . 31–38 . May 2010 . 20117892 . 10.1016/j.forsciint.2010.01.004 .
  4. Compton DR, Johnson MR, Melvin LS, Martin BR . Pharmacological profile of a series of bicyclic cannabinoid analogs: classification as cannabimimetic agents . The Journal of Pharmacology and Experimental Therapeutics . 260 . 1 . 201–209 . January 1992 . 1309872 .
  5. Martin BR, Compton DR, Thomas BF, Prescott WR, Little PJ, Razdan RK, Johnson MR, Melvin LS, Mechoulam R, Ward SJ . 6 . Behavioral, biochemical, and molecular modeling evaluations of cannabinoid analogs . Pharmacology, Biochemistry, and Behavior . 40 . 3 . 471–478 . November 1991 . 1666911 . 10.1016/0091-3057(91)90349-7 . 19386120 .
  6. Book: Bosier B, Lambert D . Introduction: The Endocannabinoid System at a Glance . 5 . Lambert DM . Cannabinoids in Nature and Medicine . 2009 . Wiley-VCH . Weinheim . 978-3-906390-56-7.
  7. Book: Stern E, Lambert D . Medicinal Chemistry Endeavors around the Phytocannabinoids . 130 . Lambert DM . Cannabinoids in Nature and Medicine . 2009 . Wiley-VCH . Weinheim . 978-3-906390-56-7.
  8. Uchiyama N, Kikura-Hanajiri R, Shoda T, Fukuhara K, Goda Y . [Isomeric analysis of synthetic cannabinoids detected as designer drugs] . Yakugaku Zasshi . 131 . 7 . 1141–1147 . 2011 . 21720146 . 10.1248/yakushi.131.1141 . free .
  9. Web site: Europol 2009 Annual Report on the implementation of Council Decision 2005/387/JHA . European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) . European Union Agency for Law Enforcement Cooperation (Europol) .
  10. Web site: Europol 2012 Annual Report on the implementation of Council Decision 2005/387/JHA . European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) . European Union Agency for Law Enforcement Cooperation (Europol) .
  11. Bileck A, Ferk F, Al-Serori H, Koller VJ, Muqaku B, Haslberger A, Auwärter V, Gerner C, Knasmüller S . 6 . Impact of a synthetic cannabinoid (CP-47,497-C8) on protein expression in human cells: evidence for induction of inflammation and DNA damage . Archives of Toxicology . 90 . 6 . 1369–1382 . June 2016 . 26194647 . 10.1007/s00204-015-1569-7 . 17730405 .
  12. Web site: UN International Drug Control Conventions . United Nations . 2017-02-15 . 2014-03-17 . https://web.archive.org/web/20140317082038/http://www.unodc.org/unodc/en/commissions/CND/conventions.html . dead .
  13. Web site: §1308.11 Schedule I. . 2017-02-15 . 2009-08-27 . https://web.archive.org/web/20090827043725/http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm . dead .
  14. Web site: Regulated Drug Rule . Vermont DOH . 2016 .

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