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Abstract
Smoking mixtures containing the cannabimimetic indoles may still be available over-the-counter
in several countries. Due to the high affinity of these compounds to the cannabinoid
receptors, their effective dose is lower than that of the marijuana products resulting
in a low concentration of the excreted metabolites accompanied by a higher psychoactive
potency. Up to now the in vivo metabolism of the cannabimimetic indoles seems to be
insufficiently investigated and no data have been published on an assay of JWH-018
in urine. In this publication the urinary metabolites of JWH-018 are reported. Using
gas and liquid chromatography combined with tandem mass spectrometry two main monohydroxylated
metabolites were identified in the forensic urine samples. Based on the differences
in their electron ionization MS/MS spectra it is supposed that one is formed by hydroxylation
of the indole ring whilst the other by hydroxylation of the N-alkyl chain. The main
metabolites are almost completely glucuroconjugated, whereas minor ones (N-despentyl
hydroxy-, carboxy-, dihydroxy-, and reduced di- and trihydroxy metabolites) were also
present in the free fraction. The parent compound was not detected in urine.
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