Illicit new psychoactive substances (NPS) are a serious threat to health throughout the world. Such NPS do not usually pass preliminary pharmacological trials. In 2014, we identified a series of five new synthetic cannabinoids with an indazole-3-carboxamide structure bearing an N-1-methoxycarbonylalkyl group. The compounds have very high cannabimimetic activity which has caused mass severe intoxication and deaths. The compounds were identified by means of gas chromatography-mass spectrometry (GC-MS), including high-resolution mass spectrometry (GC-HRMS), ultra-high-performance liquid chromatography-high-resolution tandem mass spectrometry (UHPLC-HRMS(2)), and (1)H and (13)C nuclear magnetic resonance spectroscopy (NMR). The peculiarities of mass-spectral fragmentation of the compounds after electron ionization (EI) ionization and collision-induced dissociation (CID) were studied. The analytical characteristics reported for the compounds will enable their identification in a variety of materials seized from criminals.Graphical Abstract.
N‐(2‐Methoxybenzyl)‐2,5‐dimethoxyphenethylamines (NBOMes) are synthetic phenethylamine derivatives emerging on the global drug market and reported to be associated with untoward effects in people who use drugs. Its action involves agonism at serotonin 5‐HT2A receptors, affecting cognitive and behavioral processes. However, certain isomers of NBOMes may not show any psychoactive effects. They are not controlled by legislation and can be tested as pharmaceutical drugs. This study deals with the differentiation among positional isomers of 25H‐NBOMe differing in the position of the two methoxy groups in the phenylethyl moiety of the molecule, using chromatography–mass spectrometry methods. The gas chromatography analysis showed that the isothermal mode was more efficient than the usually applied temperature‐programming mode for the separation of the mentioned isomers. Electron ionization mass spectra of 25H‐NBOMe isomers were highly similar, often resulting in a high probability of erroneous identification. However, mass spectra of their trifluoroacetyl or pentafluoropropanoyl derivatives were easily identified as they contained fragments with many significant differences. The proposed analysis using liquid chromatography–tandem mass spectrometry could distinguish the isomers of 25H‐NBOMe without the need for any derivatization.
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