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Volume 11
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10.3390/metabo11040212
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Article

25CN-NBOMe Metabolites in Rat Urine, Human Liver Microsomes and C. elegans—Structure Determination and Synthesis of the Most Abundant Metabolites

by
Anna Šuláková
1,
Jitka Nykodemová
2,
Petr Palivec
2,
Radek Jurok
3,
Silvie Rimpelová
4,
Tereza Leonhardt
4,
Klára Šíchová
1,
Tomáš Páleníček
1 and
Martin Kuchař
1,2,*
1
Department of Experimental Neurobiology, National Institute of Mental Health, Topolová 748, 250 67 Klecany, Czech Republic
2
Forensic Laboratory of Biologically Active Substances, Department of Chemistry of Natural Compounds, University of Chemistry and Technology Prague, Technická 5, 16 628 Prague, Czech Republic
3
Department of Organic Chemistry, University of Chemistry and Technology Prague, Technická 5, 16 628 Prague, Czech Republic
4
Department of Biochemistry and Microbiology, University of Chemistry and Technology Prague, Technická 5, 16 628 Prague, Czech Republic
*
Author to whom correspondence should be addressed.
Metabolites 2021, 11(4), 212; https://doi.org/10.3390/metabo11040212
Submission received: 28 February 2021 / Revised: 28 March 2021 / Accepted: 29 March 2021 / Published: 31 March 2021
(This article belongs to the Special Issue New Psychoactive Substances - Metabolism and Metabolomics)
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Abstract

N-Benzylphenethylamines are novel psychedelic substances increasingly used for research, diagnostic, or recreational purposes. To date, only a few metabolism studies have been conducted for N-2-methoxybenzylated compounds (NBOMes). Thus, the available 2,5-dimethoxy-4-(2-((2-methoxybenzyl)amino)ethyl)benzonitrile (25CN-NBOMe) metabolism data are limited. Herein, we investigated the metabolic profile of 25CN-NBOMe in vivo in rats and in vitro in Cunninghamella elegans (C. elegans) mycelium and human liver microsomes. Phase I and phase II metabolites were first detected in an untargeted screening, followed by liquid chromatography-tandem mass spectrometry (LC-MS/MS) identification of the most abundant metabolites by comparison with in-house synthesized reference materials. The major metabolic pathways described within this study (mono- and bis-O-demethylation, hydroxylation at different positions, and combinations thereof, followed by the glucuronidation, sulfation, and/or N-acetylation of primary metabolites) generally correspond to the results of previously reported metabolism of several other NBOMes. The cyano functional group was either hydrolyzed to the respective amide or carboxylic acid or remained untouched. Differences between species should be taken into account in studies of the metabolism of novel substances.
Keywords: 25CN-NBOMe; LC-MS; metabolite synthesis; metabolomics 25CN-NBOMe; LC-MS; metabolite synthesis; metabolomics

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MDPI and ACS Style

Šuláková, A.; Nykodemová, J.; Palivec, P.; Jurok, R.; Rimpelová, S.; Leonhardt, T.; Šíchová, K.; Páleníček, T.; Kuchař, M. 25CN-NBOMe Metabolites in Rat Urine, Human Liver Microsomes and C. elegans—Structure Determination and Synthesis of the Most Abundant Metabolites. Metabolites 2021, 11, 212. https://doi.org/10.3390/metabo11040212

AMA Style

Šuláková A, Nykodemová J, Palivec P, Jurok R, Rimpelová S, Leonhardt T, Šíchová K, Páleníček T, Kuchař M. 25CN-NBOMe Metabolites in Rat Urine, Human Liver Microsomes and C. elegans—Structure Determination and Synthesis of the Most Abundant Metabolites. Metabolites. 2021; 11(4):212. https://doi.org/10.3390/metabo11040212

Chicago/Turabian Style

Šuláková, Anna, Jitka Nykodemová, Petr Palivec, Radek Jurok, Silvie Rimpelová, Tereza Leonhardt, Klára Šíchová, Tomáš Páleníček, and Martin Kuchař. 2021. "25CN-NBOMe Metabolites in Rat Urine, Human Liver Microsomes and C. elegans—Structure Determination and Synthesis of the Most Abundant Metabolites" Metabolites 11, no. 4: 212. https://doi.org/10.3390/metabo11040212

APA Style

Šuláková, A., Nykodemová, J., Palivec, P., Jurok, R., Rimpelová, S., Leonhardt, T., Šíchová, K., Páleníček, T., & Kuchař, M. (2021). 25CN-NBOMe Metabolites in Rat Urine, Human Liver Microsomes and C. elegans—Structure Determination and Synthesis of the Most Abundant Metabolites. Metabolites, 11(4), 212. https://doi.org/10.3390/metabo11040212

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