Multi-milligram resolution and determination of absolute configuration of pentedrone and methylone enantiomers

The enantioresolution of pentedrone and methylone was carried out at a multi-milligram scale by liquid chromatography on a Chiralpak AS® stationary phase. The excellent enantioresolution using this column allowed to collect highly pure enantiomeric fractions, achieving enantiomeric ratios higher tha...

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Published in:Journal of chromatography. B, Analytical technologies in the biomedical and life sciences Analytical technologies in the biomedical and life sciences, 2018-11, Vol.1100-1101, p.158-164
Main Authors: Silva, Bárbara, Pereira, José A., Cravo, Sara, Araújo, Ana Margarida, Fernandes, Carla, Pinto, Madalena M.M., de Pinho, Paula Guedes, Remião, Fernando
Format: Article
Language:English
Subjects:
Absolute configuration
Chromatography, High Pressure Liquid
Circular Dichroism
Methamphetamine - analogs & derivatives
Methamphetamine - analysis
Methamphetamine - chemistry
Methylamines - analysis
Methylamines - chemistry
Methylone
Models, Molecular
Multi-milligram enantioresolution
Pentanones - analysis
Pentanones - chemistry
Pentedrone
Polysaccharide-based stationary phase
Stereoisomerism
Synthetic cathinones
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Summary:The enantioresolution of pentedrone and methylone was carried out at a multi-milligram scale by liquid chromatography on a Chiralpak AS® stationary phase. The excellent enantioresolution using this column allowed to collect highly pure enantiomeric fractions, achieving enantiomeric ratios higher than 98%. An overall recovery of 72% was achieved for pentedrone enantiomers and 80% for methylone. Furthermore, the absolute configuration of the enantiomers of both cathinones was determined for the first time by electronic circular dichroism (ECD) spectroscopy, with the aid of theoretical calculations, as (+)‑(S) and (−)‑(R)-pentedrone, and (−)‑(S) and (+)‑(R)‑methylone. •Multi-milligram enantioresolution of pentedrone and methylone was reported for the first time.•Overall recovery of 72% and 80% were achieved for pentedrone and methylone enantiomers.•Enantiomeric ratios higher than 98% were obtained.•Absolute configuration was established for the first time.•Combined ECD spectroscopy and ECD spectral simulation were used.
ISSN:1570-0232
1873-376X
DOI:10.1016/j.jchromb.2018.10.002