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Open AccessArticle

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)
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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MDPI and ACS Style

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. https://doi.org/10.3390/molecules24040818

AMA Style

Kim J-H, Kim S, Lee J, In S, Cho Y-Y, Kang HC, Lee JY, Lee HS. 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(4):818. https://doi.org/10.3390/molecules24040818

Chicago/Turabian Style

Kim, Ju-Hyun; Kim, Sunjoo; Lee, Jaesin; In, Sangwhan; Cho, Yong-Yeon; Kang, Han C.; Lee, Joo Y.; Lee, Hye S. 2019. "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 24, no. 4: 818. https://doi.org/10.3390/molecules24040818

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