Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
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Identification of a Cannabinoid Analog as a New Type of Designer Drug in a Herbal Product
Nahoko UchiyamaRuri Kikura-HanajiriNobuo KawaharaYuji HaishimaYukihiro Goda
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2009 Volume 57 Issue 4 Pages 439-441

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Abstract

A new type of designer drug, a cannabinoid analog (1), was found in a herbal product distributed on the illegal drug market in Japan in expectation of its narcotic effect. The structure of 1 was identified by LC-MS, GC-MS, high-resolution MS, and NMR analyses. Compound 1 showed a molecular weight of 332, and accurate mass measurement exhibited its elemental composition to be C22H36O2. Together, the mass and NMR spectrometric data revealed that 1 was (1RS,3SR)-3-[4-(1,1-dimethyloctyl)-2-hydroxyphenyl]cyclohexan-1-ol, which was first synthesized in 1979 by a group at Pfizer Inc. and reported as a potent cannabinoid analog possessing cannabinoid receptor binding activity and analgesic activity in the 1990s. This is the first report to identify a cannabinoid analog in an illegal drug.

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© 2009 The Pharmaceutical Society of Japan
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