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Published in: Forensic Toxicology 2/2019

Open Access 01-07-2019 | Original Article

Methylone and pentylone: structural analysis of new psychoactive substances

Authors: Dita Spálovská, Tereza Maříková, Michal Kohout, František Králík, Martin Kuchař, Vladimír Setnička

Published in: Forensic Toxicology | Issue 2/2019

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Abstract

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.
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Metadata
Title
Methylone and pentylone: structural analysis of new psychoactive substances
Authors
Dita Spálovská
Tereza Maříková
Michal Kohout
František Králík
Martin Kuchař
Vladimír Setnička
Publication date
01-07-2019
Publisher
Springer Singapore
Published in
Forensic Toxicology / Issue 2/2019
Print ISSN: 1860-8965
Electronic ISSN: 1860-8973
DOI
https://doi.org/10.1007/s11419-019-00468-z

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