International Journal of Legal Medicine

, Volume 133, Issue 3, pp 833–841 | Cite as

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

  • Hyewon Seo
  • In Sook Kim
  • Young-Hoon Kim
  • Hye Hyun YooEmail author
  • Jin HongEmail author
Short Communication


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.


25N-NBOMe Human liver microsomes Metabolism LC-Q-TOF/MS 



This study was supported by the Ministry of Food and Drug Safety of Korea (17181MFDS416).

Compliance with ethical standards

Conflict interest

The authors declare that they have no conflict of interest.

Supplementary material

414_2018_1904_MOESM1_ESM.docx (50 kb)
ESM 1 (DOCX 49 kb)
414_2018_1904_MOESM2_ESM.pdf (57 kb)
ESM 2 (PDF 57 kb)


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Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Pharmacological Research Division, Toxicological and Research Department, National Institute of Food and Drug Safety EvaluationMinistry of Food and Drug SafetyCheongwon-gunRepublic of Korea
  2. 2.Institute of Pharmaceutical Science and Technology and College of PharmacyHanyang UniversityAnsanRepublic of Korea
  3. 3.College of Pharmacy, Ewha Womans UniversitySeodaemun-guSouth Korea

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