Methylone and pentylone: structural analysis of new psychoactive substances

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F19%3A43919047" target="_blank" >RIV/60461373:22310/19:43919047 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/60461373:22330/19:43919047 RIV/60461373:22340/19:43919047 RIV/60461373:22810/19:43919047

Výsledek na webu

<a href="https://link.springer.com/article/10.1007%2Fs11419-019-00468-z" target="_blank" >https://link.springer.com/article/10.1007%2Fs11419-019-00468-z</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1007/s11419-019-00468-z" target="_blank" >10.1007/s11419-019-00468-z</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Methylone and pentylone: structural analysis of new psychoactive substances

Popis výsledku v původním jazyce

Purpose: The growing availability of new psychoactive substances with unknown toxicity is alarming all over the world. The simplicity of acquiring these drugs of abuse from internet markets has caused an increase in the total number of seizures. We present the first systematic spectroscopic study of methylone and pentylone, which are in the class of synthetic cathinones. Methods: High performance liquid chromatography (HPLC) was used for the enantioseparation of methylone and pentylone. The substances were further analysed by the conventional methods of ultraviolet (UV) and infrared (IR) absorption and chiroptical methods, specifically electronic circular dichroism (ECD) and vibrational circular dichroism (VCD). The obtained data were supported with the density functional theory (DFT) calculations using the B3LYP or B3PW91 functional and 6-311++G(d,p) basis sets, including the solvent effects. Results: The 3D structure of methylone and pentylone in solution was revealed. Moreover, the chiral separation of both studied substances was achieved and the absolute configuration of the respective enantiomers was determined. Conclusion: Vibrational circular dichroism spectroscopy seems to be the best of the methods employed to distinguish structurally similar chiral substances, especially in combination with quantum chemical calculations. According to the structural analysis, 5 and 9 stable conformers of methylone and pentylone, respectively, were revealed in an aqueous solution. Finally, very good agreement between the experimental and simulated spectra was achieved. © 2019, The Author(s).

Název v anglickém jazyce

Methylone and pentylone: structural analysis of new psychoactive substances

Popis výsledku anglicky

Purpose: The growing availability of new psychoactive substances with unknown toxicity is alarming all over the world. The simplicity of acquiring these drugs of abuse from internet markets has caused an increase in the total number of seizures. We present the first systematic spectroscopic study of methylone and pentylone, which are in the class of synthetic cathinones. Methods: High performance liquid chromatography (HPLC) was used for the enantioseparation of methylone and pentylone. The substances were further analysed by the conventional methods of ultraviolet (UV) and infrared (IR) absorption and chiroptical methods, specifically electronic circular dichroism (ECD) and vibrational circular dichroism (VCD). The obtained data were supported with the density functional theory (DFT) calculations using the B3LYP or B3PW91 functional and 6-311++G(d,p) basis sets, including the solvent effects. Results: The 3D structure of methylone and pentylone in solution was revealed. Moreover, the chiral separation of both studied substances was achieved and the absolute configuration of the respective enantiomers was determined. Conclusion: Vibrational circular dichroism spectroscopy seems to be the best of the methods employed to distinguish structurally similar chiral substances, especially in combination with quantum chemical calculations. According to the structural analysis, 5 and 9 stable conformers of methylone and pentylone, respectively, were revealed in an aqueous solution. Finally, very good agreement between the experimental and simulated spectra was achieved. © 2019, The Author(s).

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10406 - Analytical chemistry

Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>S - Specificky vyzkum na vysokych skolach

Rok uplatnění

2019

Kód důvěrnosti údajů

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

Název periodika

Forensic Toxicology

ISSN

1860-8965

e-ISSN

—

Svazek periodika

37

Číslo periodika v rámci svazku

2

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

12

Strana od-do

366-377

Kód UT WoS článku

000472181100008

EID výsledku v databázi Scopus

2-s2.0-85062700448