Identification of a cannabinoid analog as a new type of designer drug in a herbal product

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 spectromet-ric 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 cannabi-noid 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. © 2009 Pharmaceutical Society of Japan.