Literature DB >> 30336346

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

Bárbara Silva1, José A Pereira2, Sara Cravo3, Ana Margarida Araújo4, Carla Fernandes5, Madalena M M Pinto3, Paula Guedes de Pinho4, Fernando Remião4.   

Abstract

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.
Copyright © 2018 Elsevier B.V. All rights reserved.

Entities:  

Keywords:  Absolute configuration; Methylone; Multi-milligram enantioresolution; Pentedrone; Polysaccharide-based stationary phase; Synthetic cathinones

Mesh:

Substances:

Year:  2018        PMID: 30336346     DOI: 10.1016/j.jchromb.2018.10.002

Source DB:  PubMed          Journal:  J Chromatogr B Analyt Technol Biomed Life Sci        ISSN: 1570-0232            Impact factor:   3.205


  6 in total

Review 1.  Interpol review of controlled substances 2016-2019.

Authors:  Nicole S Jones; Jeffrey H Comparin
Journal:  Forensic Sci Int Synerg       Date:  2020-05-24

Review 2.  Chiral Separations in Preparative Scale: A Medicinal Chemistry Point of View.

Authors:  Madalena M M Pinto; Carla Fernandes; Maria E Tiritan
Journal:  Molecules       Date:  2020-04-21       Impact factor: 4.411

Review 3.  From Natural Products to New Synthetic Small Molecules: A Journey through the World of Xanthones.

Authors:  Madalena M M Pinto; Andreia Palmeira; Carla Fernandes; Diana I S P Resende; Emília Sousa; Honorina Cidade; Maria Elizabeth Tiritan; Marta Correia-da-Silva; Sara Cravo
Journal:  Molecules       Date:  2021-01-15       Impact factor: 4.411

Review 4.  Synthetic Cathinones: Recent Developments, Enantioselectivity Studies and Enantioseparation Methods.

Authors:  Ana Sofia Almeida; Bárbara Silva; Paula Guedes de Pinho; Fernando Remião; Carla Fernandes
Journal:  Molecules       Date:  2022-03-22       Impact factor: 4.411

5.  Determination of the chiral status of different novel psychoactive substance classes by capillary electrophoresis and β-cyclodextrin derivatives.

Authors:  Johannes S Hägele; Eva-Maria Hubner; Martin G Schmid
Journal:  Chirality       Date:  2020-07-15       Impact factor: 2.437

6.  Enantioselectivity of Pentedrone and Methylone on Metabolic Profiling in 2D and 3D Human Hepatocyte-like Cells.

Authors:  Bárbara Silva; Joana Saraiva Rodrigues; Ana Sofia Almeida; Ana Rita Lima; Carla Fernandes; Paula Guedes de Pinho; Joana Paiva Miranda; Fernando Remião
Journal:  Pharmaceuticals (Basel)       Date:  2022-03-17
  6 in total

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