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25CN-NBOMe Metabolites in Rat Urine, Human Liver Microsomes and C.elegans-Structure Determination and Synthesis of the Most Abundant Metabolites.
Suláková, Anna; Nykodemová, Jitka; Palivec, Petr; Jurok, Radek; Rimpelová, Silvie; Leonhardt, Tereza; Síchová, Klára; Pálenícek, Tomás; Kuchar, Martin.
Afiliação
  • Suláková A; Department of Experimental Neurobiology, National Institute of Mental Health, Topolová 748, 250 67 Klecany, Czech Republic.
  • Nykodemová J; 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.
  • Palivec P; 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.
  • Jurok R; Department of Organic Chemistry, University of Chemistry and Technology Prague, Technická 5, 16 628 Prague, Czech Republic.
  • Rimpelová S; Department of Biochemistry and Microbiology, University of Chemistry and Technology Prague, Technická 5, 16 628 Prague, Czech Republic.
  • Leonhardt T; Department of Biochemistry and Microbiology, University of Chemistry and Technology Prague, Technická 5, 16 628 Prague, Czech Republic.
  • Síchová K; Department of Experimental Neurobiology, National Institute of Mental Health, Topolová 748, 250 67 Klecany, Czech Republic.
  • Pálenícek T; Department of Experimental Neurobiology, National Institute of Mental Health, Topolová 748, 250 67 Klecany, Czech Republic.
  • Kuchar M; Department of Experimental Neurobiology, National Institute of Mental Health, Topolová 748, 250 67 Klecany, Czech Republic.
Metabolites ; 11(4)2021 Mar 31.
Article em En | MEDLINE | ID: mdl-33807281
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.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Ano de publicação: 2021 Tipo de documento: Article

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Ano de publicação: 2021 Tipo de documento: Article