Metabolic profile determination of 25N-NBOMe in human liver microsomes by liquid chromatography-quadrupole time-of-flight mass spectrometry
- Authors
- Seo, Hyewon; Kim, In Sook; Kim, Young-Hoop; Yoo, Hye Hyun; Hong, Jin
- Issue Date
- May-2019
- Publisher
- SPRINGER
- Keywords
- 25N-NBOMe; Human liver microsomes; Metabolism; LC-Q-TOF/MS
- Citation
- INTERNATIONAL JOURNAL OF LEGAL MEDICINE, v.133, no.3, pp.833 - 841
- Indexed
- SCIE
SCOPUS
- Journal Title
- INTERNATIONAL JOURNAL OF LEGAL MEDICINE
- Volume
- 133
- Number
- 3
- Start Page
- 833
- End Page
- 841
- URI
- https://scholarworks.bwise.kr/erica/handle/2021.sw.erica/2983
- DOI
- 10.1007/s00414-018-1904-7
- ISSN
- 0937-9827
- 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.
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