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

Chem Pharm Bull (Tokyo). 2009 Apr;57(4):439-41. doi: 10.1248/cpb.57.439.

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 C(22)H(36)O(2). 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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cannabinoids / chemistry
  • Cannabinoids / isolation & purification*
  • Designer Drugs / chemistry*
  • Dronabinol / chemistry
  • Molecular Conformation
  • Molecular Weight
  • Plant Preparations / chemistry*

Substances

  • (1RS,3SR)-3-(4-(1,1-dimethyloctyl)-2-hydroxyphenyl)cyclohexan-1-ol
  • Cannabinoids
  • Designer Drugs
  • Plant Preparations
  • Dronabinol