Metabolic profile determination of 25N-NBOMe in human liver microsomes by liquid chromatography-quadrupole time-of-flight mass spectrometry.

The synthetic psychoactive substance 25N-NBOMe, a phenethylamine, was metabolized in vitro using human liver microsomes. Fourteen metabolites (M1–M14) were identified through liquid chromatography-quadrupole time-of-flight mass spectrometry. The biotransformations included hydroxylation, O-demethylation, N-dealkylation, nitro reduction, dehydrogenation, and carbonylation. The hydroxyl metabolite was the most abundant after phase I metabolism. These findings offer potential biomarkers for detecting 25N-NBOMe ingestion.

Study at a glance

Abstract

2-(2,5-Dimethoxy-4-nitrophenyl)-N-(2-methoxybenzyl)ethanamine (25N-NBOMe, 2C-N-NBOMe, NBOMe-2C-N) is a novel synthetic psychoactive substance of the phenethylamine chemical class. A few metabolism studies have been conducted for 25I-NBOMe, 25B-NBOMe, and 25C-NBOMe, and others, whereas 25N-NBOMe metabolism has not been researched. In this study, the in vitro metabolism of 25N-NBOMe was investigated with human liver microsomes, and the reaction mixture was analyzed using liquid chromatography-quadrupole time-of-flight mass spectrometry (LC-Q-TOF/MS). Formation of 14 metabolites (M1-M14) was yielded with incubation of 25N-NBOMe in human liver microsomes in the presence of NADPH. The metabolites were structurally characterized on the basis of accurate mass analysis and MS/MS fragmentation patterns. The biotransformations included hydroxylation, O-demethylation, N-dealkylation, nitro reduction, dehydrogenation, carbonylation, and combinations thereof. Hydroxyl metabolite was the most abundant compound after the phase I process. These results provide helpful information establishing biomarkers in case of 25N-NBOMe ingestion.