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In Vitro Metabolism of 25B-NBF, 2-(4-Bromo-2,5-Dimethoxyphenyl)-N-(2-Fluorobenzyl)ethanamine, in Human Hepatocytes Using Liquid Chromatography–Mass Spectrometry

1
BK21 PLUS Team for Creative Leader Program for Pharmacomics-based Future Pharmacy, College of Pharmacy, The Catholic University of Korea, Bucheon 14662, Korea
2
College of Pharmacy, Yeungnam University, Gyeongsan 38541, Korea
3
National Forensic Service, Wonju 24460, Korea
*
Author to whom correspondence should be addressed.
Academic Editor: Ki-Jung Paeng
Molecules 2019, 24(4), 818; https://doi.org/10.3390/molecules24040818
Received: 29 January 2019 / Revised: 17 February 2019 / Accepted: 22 February 2019 / Published: 25 February 2019
(This article belongs to the Special Issue Forensic Analytical Chemistry)
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Abstract

25B-NBF, 2-(4-bromo-2,5-dimethoxyphenyl)-N-(2-fluorobenzyl)ethanamine, is a new psychoactive substance classified as a phenethylamine. It is a potent agonist of the 5-hydroxytryptamine receptor, but little is known about its metabolism and elimination properties since it was discovered. To aid 25B-NBF abuse screening, the metabolic characteristics of 25B-NBF were investigated in human hepatocytes and human cDNA-expressed cytochrome P450 (CYP) and UDP-glucuronosyltransferase (UGT) enzymes using liquid chromatography–high resolution mass spectrometry. At a hepatic extraction ratio of 0.80, 25B-NBF was extensively metabolized into 33 metabolites via hydroxylation, O-demethylation, bis-O-demethylation, N-debenzylation, glucuronidation, sulfation, and acetylation after incubation with pooled human hepatocytes. The metabolism of 25B-NBF was catalyzed by CYP1A1, CYP1A2, CYP2B6, CYP2C9, CYP2C19, CYP2D6, CYP2J2, CYP3A4, and UGT2B7 enzymes. Based on these results, it is necessary to develop a bioanalytical method for the determination of not only 25B-NBF but also its metabolites in biological samples for the screening of 25B-NBF abuse. View Full-Text
Keywords: 25B-NBF metabolism; liquid chromatography-high resolution mass spectrometry; human hepatocyte; CYP; UGT 25B-NBF metabolism; liquid chromatography-high resolution mass spectrometry; human hepatocyte; CYP; UGT
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Kim, J.-H.; Kim, S.; Lee, J.; In, S.; Cho, Y.-Y.; Kang, H.C.; Lee, J.Y.; Lee, H.S. In Vitro Metabolism of 25B-NBF, 2-(4-Bromo-2,5-Dimethoxyphenyl)-N-(2-Fluorobenzyl)ethanamine, in Human Hepatocytes Using Liquid Chromatography–Mass Spectrometry. Molecules 2019, 24, 818.

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