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CP 47,497
CP 47,497 or (C7)-CP 47,497 is a cannabinoid receptor agonist drug, developed by Pfizer in the 1980s.〔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〕 It has analgesic effects and is used in scientific research. It is a potent CB1 agonist with a Kd of 2.1nM.〔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〕〔Roger Pertwee. Cannabinoids. Handbook of Experimental Pharmacology Volume 168. Springer. ISBN 3-540-22565-X〕〔Little PJ, ''et al.'' Pharmacology and stereoselectivity of structurally novel cannabinoids in mice. ''Journal of Pharmacology and Experimental Therapeutics'' 1988; 247:1046–1051.〕
==Homologue==
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. Both the dimethylheptyl and dimethyloctyl homologues were detected in different batches, with considerable variation in the concentration present in different samples that were analysed. The weaker dimethylhexyl and dimethylnonyl homologues were not found in any batches of smoking blends tested, but have been legally scheduled alongside the others in some jurisdictions, to forestall any potential use for this purpose.〔Hauptwirkstoff von „Spice“ identifiziert, University of Freiburg http://www.pr.uni-freiburg.de/pm/2009/pm.2009-01-19.19/〕〔Spice - weitere Analyseresultate http://www.basg.at/servlet/sls/Tornado/web/ages/content/4E5A4B86295BF5C0C125753E006A5E3C〕〔Auwärter V, ''et al.'' 'Spice' and other herbal blends: harmless incense or cannabinoid designer drugs? ''Journal of Mass Spectrometry''. 2009 Feb 2. PMID 19189348〕 The 1,1-dimethyloctyl homologue of CP 47,497 is in fact several times more potent than the parent compound,〔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〕 which is somewhat unexpected as the 1,1-dimethylheptyl is the most potent substituent in classical cannabinoid compounds such as HU-210.〔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〕 The unapproved use of these compounds in herbal smoking blends has led to a resurgence in legitimate scientific research into their use,〔Uchiyama N, ''et al.'' Effects of synthetic cannabinoids on electroencephalogram power spectra in rats. Forensic Science International. 2011 Jun 1. PMID 21640532〕 and consequently the C8 homologue of CP 47,497 has been assigned a proper name, cannabicyclohexanol.
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