Metabolic profile determination of 25N-NBOMe in human liver microsomes by liquid chromatography-quadrupole time-of-flight mass spectrometry - PubMed (original) (raw)

. 2019 May;133(3):833-841.

doi: 10.1007/s00414-018-1904-7. Epub 2018 Aug 9.

Affiliations

• PMID: 30090972
• DOI: 10.1007/s00414-018-1904-7

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

Hyewon Seo et al. Int J Legal Med. 2019 May.

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.

Keywords: 25N-NBOMe; Human liver microsomes; LC-Q-TOF/MS; Metabolism.

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References

1. 1. Welter-Luedeke J, Maurer HH (2016) New psychoactive substances: chemistry, pharmacology, metabolism, and detectability of amphetamine derivatives with modified ring systems. Ther Drug Monit 38:4–11 - DOI
2. 1. World Health Organization (WHO) (2014) WHO Agenda item 4.19 Expert Committee on Drug Dependence Thirty-Sixth Meeting. http://www.who.int/medicines/areas/quality_safety/4_19_EPR_2.pdf. Accessed 12 Feb 2018
3. 1. Wood DM, Sedefov R, Cunningham A, Dargan PI (2015) Prevalence of use and acute toxicity associated with the use of NBOMe drugs. Clin Toxicol (Phila) 53:85–92 - DOI
4. 1. Suzuki J, Dekker MA, Valenti ES, Arbelo Cruz FA, Correa AM, Poklis JL, Poklis A (2015) Toxicities associated with NBOMe ingestion-a novel class of potent hallucinogens: a review of the literature. Psychosomatics 56:129–139 - DOI
5. 1. World Health Organization (WHO) (2014) WHO Agenda item 4.17 Expert Committee on Drug Dependence Thirty-Sixth Meeting. http://www.who.int/medicines/areas/quality_safety/4_17_EPR_1.pdf . Accessed 12 Feb 2018

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