Stereoselective Metabolism of Cannabis Drugs Responsible for Toxicity

The variance in the toxic effects of designer cannabis drugs marketed throughout Europe and the USA as “K2” or “Spice” could be the result of stereoselective metabolism of enantiomers by lung and liver enzymes, according to a study published in Analytical Chemistry. Chiral liquid chromatography–tandem mass spectrometry (LC–MS–MS) was applied to the analysis of JWH–018 and AM2201 metabolites in human urine. JWH–018 and AM2201 are metabolized by lung and liver enzymes to generate three primary chiral metabolites — (ω)-carboxyl, (ω)-monohydroxyl, and (ω-1)-monohydroxyl metabolites that have a high affinity for the human cannabinoid type-1 receptor (CB1R). Solid-phase extraction with chiral LC–MS–MS determined specific excretion patterns associated with both JWH–018 and AM2201 compound metabolism. The authors suggest the method could be used in future clinical studies.

Reference

A.L. Patton et al., Anal. Chem.85, 9390–9399 (2013).

This story originally appeared in The Column. Click here to view that issue.