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CP 47,497
Systematic (IUPAC) name
2-[(1R,3S)-3-hydroxycyclohexyl]- 5-(2-methyloctan-2-yl)phenol
Identifiers
CAS number 70434-82-1
70434-92-3 (C8 homologue)
ATC code  ?
PubChem 125835
Chemical data
Formula C 21H34O2  
Mol. mass 318.492 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status Illegal in Germany and France
Routes  ?

CP 47,497 is a cannabinoid receptor agonist drug, developed by Pfizer in the 1980s.[1] It has analgesic effects and is used in scientific research. It is a potent CB1 agonist with a Kd of 2.1 nM.[2][3][4]

On the 19th of January 2009, the University of Freiburg in Germany announced that an analog of CP 47,497 is the main active ingredient in the herbal "incense" product Spice, specifically the 1,1-dimethyloctyl homologue of CP 47,497.[5][6][7] The 1,1-dimethyloctyl homologue of CP 47,497 is in fact several times more potent than the parent compound,[8] which is somewhat unexpected as the 1,1-dimethylheptyl is the most potent substituent in classical cannabinoid compounds such as HU-210.[9]

Contents

Legal Status

Germany

On the 22nd January 2009, CP 47,497 was added to the German controlled drug schedules ("Betäubungsmittelgesetz"),[10] along with its dimethylhexyl, dimethyloctyl and dimethylnonyl homologues.[11]

France

CP 47,497 and its C6, C8, and C9 homologues were made illegal in France on 24th of February 2009.[12]

Latvia

CP 47,497 and its C6, C8, and C9 homologues were made illegal in Latvia on 28 November 2009.[13]

Lithuania

CP 47,497 and its C6, C8, and C9 homologues were made illegal in Lithuania on 5th of June 2009.[14]

Sweden

CP 47,497 and its C6, C7, C8, and C9 homologues were made illegal in Sweden on 15th of September 2009.

References

  1. ^ Weissman A, Milne GM, Melvin LS Jr. Cannabimimetic activity from CP-47,497, a derivative of 3-phenylcyclohexanol. Journal of Pharmacology and Experimental Therapeutics. 1982 Nov;223(2):516-23. PMID 6290642
  2. ^ Shim JY, Welsh WJ, Howlett AC. Homology model of the CB1 cannabinoid receptor: sites critical for nonclassical cannabinoid agonist interaction. Biopolymers. 2003;71(2):169-89. PMID 12767117
  3. ^ Roger Pertwee. Cannabinoids. Handbook of Experimental Pharmacology Volume 168. Springer. ISBN 3-540-22565-X
  4. ^ Little PJ, Compton DR, Johnson MR, Melvin LS, Martin BR. Pharmacology and stereoselectivity of structurally novel cannabinoids in mice. Journal of Pharmacology and Experimental Therapeutics 1988; 247:1046–1051.
  5. ^ Hauptwirkstoff von „Spice“ identifiziert, University of Freiburg http://www.pr.uni-freiburg.de/pm/2009/pm.2009-01-19.19/
  6. ^ Spice - weitere Analyseresultate http://www.basg.at/servlet/sls/Tornado/web/ages/content/4E5A4B86295BF5C0C125753E006A5E3C
  7. ^ 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. 2009 Feb 2. PMID 19189348
  8. ^ 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
  9. ^ Martin BR, Compton DR, Thomas BF, Prescott WR, Little PJ, Razdan RK, Johnson MR, Melvin LS, Mechoulam R, Ward SJ. Behavioral, biochemical, and molecular modeling evaluations of cannabinoid analogs. Pharmacology, Biochemistry and Behavior. 1991 Nov;40(3):471-8. PMID 1666911
  10. ^ Modedroge "Spice" ist verboten!
  11. ^ BGBl I Nr. 3 vom 21.01.2009, 22. BtMÄndV vom 19. Januar 2009, S. 49–50.
  12. ^ [1]
  13. ^ [2]
  14. ^ http://www3.lrs.lt/pls/inter3/dokpaieska.showdoc_l?p_id=345197







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