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

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F21%3A43922266" target="_blank" >RIV/60461373:22310/21:43922266 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/60461373:22330/21:43922266 RIV/00023752:_____/21:43920583

Výsledek na webu

<a href="https://www-mdpi-com.ezproxy.vscht.cz/2218-1989/11/4/212" target="_blank" >https://www-mdpi-com.ezproxy.vscht.cz/2218-1989/11/4/212</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.3390/metabo11040212" target="_blank" >10.3390/metabo11040212</a>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10608 - Biochemistry and molecular biology

Projekt

<a href="/cs/project/VI20172020056" target="_blank" >VI20172020056: Nové syntetické drogy - komplexní mezioborové výzkumné centrum</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2021

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Metabolites

ISSN

2218-1989

e-ISSN

—

Svazek periodika

11

Číslo periodika v rámci svazku

4

Stát vydavatele periodika

CH - Švýcarská konfederace

Počet stran výsledku

18

Strana od-do

"nestrankovano"

Kód UT WoS článku

000643280900001

EID výsledku v databázi Scopus

2-s2.0-85104279714