Structural spectroscopic study of enantiomericallypure synthetic cathinones and their majormetabolites

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F21%3A43920620" target="_blank" >RIV/60461373:22310/21:43920620 - isvavai.cz</a>

Alternative codes found

RIV/60461373:22330/21:43920620 RIV/60461373:22340/21:43920620 RIV/60461373:22810/21:43920620

Result on the web

<a href="https://pubs.rsc.org/en/content/articlehtml/2021/nj/d0nj05065b" target="_blank" >https://pubs.rsc.org/en/content/articlehtml/2021/nj/d0nj05065b</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1039/d0nj05065b" target="_blank" >10.1039/d0nj05065b</a>

Result language

angličtina

Original language name

Structural spectroscopic study of enantiomericallypure synthetic cathinones and their majormetabolites

Original language description

New psychoactive substances (NPSs) have become a popular alternative to illicit drugs of abuse. However, to determine their metabolic pathways in the human organism, a detailed knowledge of their structure is crucial. Here, we present a comprehensive spectroscopic structural study of synthetic cathinones (clephedrone, flephedrone, and brephedrone) and their major human metabolites, desmethyl derivatives. Chiral high-performance liquid chromatography was utilized to obtain the individual enantiomers of the parent synthetic cathinones and their assumed major metabolites synthesized de novo. The developed chromatographic method made it possible to obtain the target optically pure substances on a multimilligram scale. Electronic and vibrational circular dichroism, combined with infrared and ultraviolet spectroscopy and supported by DFT calculations, were used to determine their absolute configuration and the chiroptical methods to elucidate their molecular structure in detail. Two stable conformers of each substance were found in aqueous solution. Their relative abundances were estimated based on the Boltzmann distribution and the population weighted spectra were obtained. Very good agreement was achieved between the experimental and simulated spectra, enabling the 3D structures of the studied substances to be determined in aqueous solution.

Czech name

—

Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

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OECD FORD branch

10406 - Analytical chemistry

Project

Result was created during the realization of more than one project. More information in the Projects tab.

Continuities

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

Publication year

2021

Confidentiality

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

Name of the periodical

New Journal of Chemistry

ISSN

1144-0546

e-ISSN

—

Volume of the periodical

45

Issue of the periodical within the volume

2

Country of publishing house

GB - UNITED KINGDOM

Number of pages

11

Pages from-to

850-860

UT code for WoS article

000609189100039

EID of the result in the Scopus database

2-s2.0-85099541201