Conformational analysis of amphetamine and methamphetamine: a comprehensive approach by vibrational and chiroptical spectroscopy

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00023752%3A_____%2F23%3A43921108" target="_blank" >RIV/00023752:_____/23:43921108 - isvavai.cz</a>

Alternative codes found

RIV/61989592:15310/23:73618892 RIV/60461373:22310/23:43925925 RIV/60461373:22330/23:43925925 RIV/60461373:22340/23:43925925

Result on the web

<a href="https://pubs.rsc.org/en/content/articlelanding/2023/AN/D2AN02014A" target="_blank" >https://pubs.rsc.org/en/content/articlelanding/2023/AN/D2AN02014A</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1039/d2an02014a" target="_blank" >10.1039/d2an02014a</a>

Result language

angličtina

Original language name

Conformational analysis of amphetamine and methamphetamine: a comprehensive approach by vibrational and chiroptical spectroscopy

Original language description

After cannabis, the most commonly used illicit substance worldwide is amphetamine and its derivatives, such as methamphetamine, with an ever-increasing number of synthetic modifications. Thus, fast and reliable methods are needed to identify them according to their spectral patterns and structures. Here, we have investigated the use of molecular spectroscopy methods to describe the 3D structures of these substances in a solution that models the physiological environment. The substances were analyzed by Raman and infrared (IR) absorption spectroscopy and by chiroptical methods, vibrational circular dichroism (VCD) and Raman optical activity (ROA). The obtained experimental data were supported by three different computational approaches based on density functional theory (DFT) and molecular dynamics (MD). Successful interpretation relies on good agreement between experimental and predicted spectra. The determination of the conformer populations of the studied molecules was based on maximizing the similarity overlap of weighted conformer spectra by a global minimization algorithm. Very good agreement was obtained between the experimental spectra and optimized-population weighted spectra from MD, providing a detailed insight into the structure of the molecules and their interaction with the solvent. The relative population of three amphetamine and six methamphetamine conformers was determined and is consistent with a previous NMR study. However, this work shows that only a few isolated conformers are not sufficient for the successful interpretation of the spectra, but the entire conformational space needs to be sampled appropriately and explicit interaction with the solvent needs to be included.

Czech name

—

Czech description

—

Type

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

CEP classification

—

OECD FORD branch

10401 - Organic chemistry

Project

<a href="/en/project/GA22-04669S" target="_blank" >GA22-04669S: Sensitivity Enhancement of Vibrational Optical Activity Spectroscopy for Biomolecules</a><br>

Continuities

V - Vyzkumna aktivita podporovana z jinych verejnych zdroju

Publication year

2023

Confidentiality

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

Name of the periodical

Analyst

ISSN

0003-2654

e-ISSN

1364-5528

Volume of the periodical

148

Issue of the periodical within the volume

6

Country of publishing house

GB - UNITED KINGDOM

Number of pages

12

Pages from-to

1337-1348

UT code for WoS article

000941197600001

EID of the result in the Scopus database

2-s2.0-85149325772