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Uchiyama N, Kikura-Hanajiri R, Kawahara N, Haishima Y, Goda Y. 
“Identification of a cannabinoid analog as a new type of designer drug in a herbal product”. 
Chem Pharm Bull Tokyo. 2009 Apr 01;57(4):439-41.
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 1990 s. This is the first report to identify a cannabinoid analog in an illegal drug.
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