YAKUGAKU ZASSHI
Online ISSN : 1347-5231
Print ISSN : 0031-6903
ISSN-L : 0031-6903
資料
デザイナードラッグとして検出された合成カンナビノイドの異性体分析について
内山 奈穂子花尻(木倉) 瑠理正田 卓司福原 潔合田 幸広
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ジャーナル フリー

2011 年 131 巻 7 号 p. 1141-1147

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  Recently, many psychotropic herbal products, named such as “Spice”, were distributed worldwide via the Internet. In our previous study, several synthetic cannabinoids were identified as adulterants in herbal products being available in Japan due to their expected narcotic effects. Among those, two derivatives of Δ9-tetrahydrocannabinol (Δ9-THC), which is major psychotropic cannabinoid of marijuana, cannabicyclohexanol (CCH, 3-[2-hydroxy-4-(2-methylnonan-2-yl)phenyl]cyclohexan-1-ol) and CP-47,497 (3-[2-hydroxy-4-(2-methyloctan-2-yl)phenyl]cyclohexan-1-ol), have been controlled as designated substances (Shitei-Yakubutsu) under the Pharmaceutical Affairs Law since November 2009. CCH was detected together with its trans-form (1-epimer) in many herbal products, and CCH and CP-47,497 have two chiral centers in the structures. However, the pharmaceutical activities of the isomers of CCH have not been reported. This study presents chiral separations of CCH, its trans-form and CP-47,497 in the products using LC-circular dichroism (CD) and LC-MS analyses. The enantiomeric pairs of CCH, its trans-form and CP-47,497 were separated, respectively. Subsequently, the analyses of the herbal products showed that CCH and its trans-form existed as mixtures of enantiomers and the relative ratios of CCH and the trans-form enantiomers ranged from 42/58% to 53/47% and from 33/67% to 52/48%, respectively.

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© 2011 by the PHARMACEUTICAL SOCIETY OF JAPAN
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