Enantioseparationof 3-chloromethcathinone by liquid chromatography at the milligram scale

Langa, Ivan; Ribeiro, Cláudia; Gonçalves, Virgínia; Dias da Silva, Diana; Cravo, Sara; Tiritan, Maria; Dias da Silva, Diana Cristina

http://hdl.handle.net/10400.22/31507

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Authors

Dias da Silva, Diana Cristina

Abstract(s)

The most prominent synthetic cathinone (SCAT)is 3-chloromethcathinone (3-CMC), accounting for 34% and 63.41% of the total seized new psychoactive substances (NPS) in Europe in 2021 and 2022, respectively [1, 2].Over the latest years, since the first identification on the European drug market in September 2014 in Sweden, 3-CMC has gained significant popularity among the younger drug users [3]. Moreover, 3-CMC is chiral and its enantiomers can show different biological activity, highlighting the importance of the enantio selectivity studies in clinical, forensic and ecotoxicological context. The aim of this study was to optimize a chromatographic method for the enantiomeric separation of 3-CMC at the milligram scale for further use in in vitroand ecotoxicity assessments. The enantio separation as well as the enantiomeric purity evaluation of the 3-CMC were performed by liquid chromatography coupled to the ultraviolet-visible detector (UV/Vis), using a CHIRALPAK®AD-H 10x250mm, 5 μm, a semi-preparative column. A Dionex Ultimate 3000 automated fraction collector was used for fractions collection. Data was analyzed by Chromeleon 7.0 software. For method conditions optimization, a solution at 100 μgmL-1of 3-CMC in ethanol with diethylamine was used. The optimized method allowed the separation of the enantiomers of 3-CMCat final concentration of 3.7 mg mL-1, with an enantiomeric purity of 98 % and 95 % for the first and second eluted enantiomer, respectively. The determination of the absolute configuration of theenantiomers is ongoing by electronic circular dichroism. The isolated enantiomers will be used for the enantio selective evaluation of the 3-CMC ecotoxicity.The determination of the absolute configuration of the enantiomers will enable correlating the ecotoxicity of each enantiomer.

Keywords

3-chloromethcathinone Enantioseparation Synthetic cathinones

URI

http://hdl.handle.net/10400.22/31507

Citation

Langa, I., Ribeiro, C., Gonçalves, V., Dias-da-Silva, D., Cravo, S., & Tiritan, M. (2025). Enantioseparation of 3-chloromethcathinone by liquid chromatography at the milligram scale. IV 1H-TOXRUN INTERNATIONAL CONGRESS 2025 - Scientific Letters - Book of Abstracts, 1 (Sup1). https://doi.org/10.48797/sl.2025.370