A structural spectroscopic study of dissociative anaesthetic methoxphenidine

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00023752%3A_____%2F23%3A43921057" target="_blank" >RIV/00023752:_____/23:43921057 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/60461373:22310/23:43926075 RIV/60461373:22330/23:43926075 RIV/60461373:22340/23:43926075

Výsledek na webu

<a href="https://pubs.rsc.org/en/content/articlelanding/2023/NJ/D2NJ06126K" target="_blank" >https://pubs.rsc.org/en/content/articlelanding/2023/NJ/D2NJ06126K</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1039/d2nj06126k" target="_blank" >10.1039/d2nj06126k</a>

Jazyk výsledku

angličtina

Název v původním jazyce

A structural spectroscopic study of dissociative anaesthetic methoxphenidine

Popis výsledku v původním jazyce

Methoxphenidine was originally patented for its properties to treat neurotoxic injury. However, due to its side effects, it failed to become a drug and later reappeared on the black market among so-called new psychoactive substances. Methoxphenidine belongs among dissociative anaesthetics, which came to the forefront of medicinal interest due to their potential for depression treatment. Despite its pharmacological history and black market availability, there is still a lack of pharmacological data on this substance and a shortage of methods enabling further biological studies. To offer tools for psychopharmacological studies of the enantiomers of this compound, we have developed a chiral resolution process by crystallization using a natural pool of chiral substances. We further developed a novel analytical method to control the optical purity of the obtained enantiomers using chiral supercritical fluid chromatography, which represents the contemporary green and sustainable method for chiral separation. To determine the absolute configuration of the crystallized enantiomers, we employed a combination of the electronic circular dichroism spectra supported by quantum chemical calculations. Furthermore, to verify our approach, we analysed the sample by single crystal diffraction. We believe that the tools within our work that enable pharmacological studies focused on both enantiomers of methoxphenidine may be useful not only for medicinal chemists but also for the broader scientific community.

Název v anglickém jazyce

A structural spectroscopic study of dissociative anaesthetic methoxphenidine

Popis výsledku anglicky

Methoxphenidine was originally patented for its properties to treat neurotoxic injury. However, due to its side effects, it failed to become a drug and later reappeared on the black market among so-called new psychoactive substances. Methoxphenidine belongs among dissociative anaesthetics, which came to the forefront of medicinal interest due to their potential for depression treatment. Despite its pharmacological history and black market availability, there is still a lack of pharmacological data on this substance and a shortage of methods enabling further biological studies. To offer tools for psychopharmacological studies of the enantiomers of this compound, we have developed a chiral resolution process by crystallization using a natural pool of chiral substances. We further developed a novel analytical method to control the optical purity of the obtained enantiomers using chiral supercritical fluid chromatography, which represents the contemporary green and sustainable method for chiral separation. To determine the absolute configuration of the crystallized enantiomers, we employed a combination of the electronic circular dichroism spectra supported by quantum chemical calculations. Furthermore, to verify our approach, we analysed the sample by single crystal diffraction. We believe that the tools within our work that enable pharmacological studies focused on both enantiomers of methoxphenidine may be useful not only for medicinal chemists but also for the broader scientific community.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

30107 - Medicinal chemistry

Projekt

<a href="/cs/project/GC21-31139J" target="_blank" >GC21-31139J: Nové chirální ionexy pro chromatografické enantioseparace</a><br>

Návaznosti

V - Vyzkumna aktivita podporovana z jinych verejnych zdroju

Rok uplatnění

2023

Kód důvěrnosti údajů

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

Název periodika

New Journal of Chemistry

ISSN

1144-0546

e-ISSN

1369-9261

Svazek periodika

47

Číslo periodika v rámci svazku

9

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

9

Strana od-do

4543-4551

Kód UT WoS článku

000929484000001

EID výsledku v databázi Scopus

2-s2.0-85149043713