Chiral Resolution and Enantioselectivity of Synthetic Cathinones: A Brief Review

Abstract

Chiral discrimination has become one of the most important fields in analytical and medicinal chemistry, and forensic toxicology. The enantiomers may have different binding to proteins that may lead to many pharmacological and toxicological differences between them, including kinetic (at the absorption, distribution, metabolism and excretion level) or dynamic (level of potency and efficacy or even differences in mechanism of action) variations. Cathinone derivatives are chiral compounds, sold via the internet for recreational use, and little is known about their enantiomeric selectivity. Consequently, it is of crucial importance for the development of resolution methods to obtain pure enantiomers to study their biological effects. In the last few years, techniques for chiral drug analysis, as chromatography, have been developed and some works related to the analytical enantiomeric resolution of synthetic cathinones were described. However, information about synthetic cathinones in the literature is scarce specially concerning single enantiomers. In this mini-review, analytical chiral resolution and biological differences between enantiomers of cathinone derivatives will be addressed.

Enantiospecific Synthesis, Chiral Separation, and Biological Activity of Four Indazole-3-Carboxamide-Type Synthetic Cannabinoid Receptor Agonists and Their Detection in Seized Drug Samples

“…There is a growing interest in the chromatographic separation of the increasing diversity of chiral NPS (as well as more traditional drugs of abuse such as amphetamine and methamphetamine), to gain additional information on the synthetic routes used in their manufacture and to indicate their inherent potency and efficacy (Taschwer et al, 2017; Kadkhodaei et al, 2018; Silva et al, 2018). There are opportunities to add chiral profiling to existing drug profiling methodologies if there is reproducible variation in the chiral profiles of precursor materials, even if the absolute differences are small.…”

Chiral derivatives of xanthones and benzophenones: Synthesis, enantioseparation, molecular docking, and tumor cell growth inhibition studies

“…Separation of enantiomers has become a pivotal task in several research fields, including pharmaceutical and medicinal chemistry, 1 since enantiomers of drugs and promising bioactive compounds may have different pharmacokinetic and pharmacodynamic properties 2,3 as well as diverse toxicological effects 4,5 . These are the reasons why the regulatory authorities advocate more on strict investigation and requirements for evaluating the safety and efficacy of new drugs containing stereogenic centers 6 .…”

Chiral Stationary Phases for Liquid Chromatography: Recent Developments

“…LC using chiral stationary phases (CSPs) proved to be an essential tool with a wide range of applications, including preparative separation of enantiomers of diverse analytes [16,17], determination of enantiomeric composition [18,19], monitorization of asymmetric reactions [20,21], analysis of the stereochemistry of natural compounds [22,23], pharmacokinetic [24,25], forensic [26,27,28], environmental [29,30,31], and enantioselective studies [32,33], among others.…”