Open Access 01-07-2019 | Original Article
Methylone and pentylone: structural analysis of new psychoactive substances
Published in: Forensic Toxicology | Issue 2/2019
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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.