A Simple HPLC–UV Approach for Rapid Enantioseparation of Cathinones, Pyrovalerones and Other Novel Psychoactive Substances on a 2.5-µm Cellulose Tris-(3,5-dimethylphenyl-carbamate) Column

Abstract

The misuse of so called novel psychoactive substances is still a challenging problem worldwide. A special attribute of a lot of these compounds is a chiral centre enabling two possible enantiomers probably related to different pharmacological and toxicological properties. The goal of the present study was to present a simple and isocratic HPLC-UV method for enantioseparation of mainly cathinone and pyrovalerone derivatives as well as selected representatives of amphetamines, ketamines, benzofuries, phenidines, phenidates, morpholines and thiophenes. A Waters Acquity UPC2 ® Trefoil™ CEL1 2.5 µm, 3.0 × 150 mm column served as chiral stationary phase by means of cellulose tris-(3,5-dimethylphenylcarbamate) as chiral selector. Mobile phases consisted either of n-hexane/n-butanol/diethylamine (100:0.3:0.2) or n-hexane/diethylamine (100:0.2). The method was found to be applicable for rapid simultaneous chiral separations of cathinone derivatives, to determine enantiomeric elution orders, to detect positional isomers and to identify real-life samples. Also, a repeatability study was performed successfully. 78 out of 95 compounds were separated in their enantiomers successfully, 51 of them within 6 min. It was shown that all NPS bought from online vendors or seized by police were traded as racemic mixtures.Publisher's Note Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Identification of synthetic cathinones in seized materials: A review of analytical strategies applied in forensic chemistry

“…Reports on the detection of synthetic cathinones isomers by LC‐DAD or LC‐UV are also available. An example is the reported separation of 49 cathinones using a LC with diode‐array detection, employing a chiral stationary phase with cellulose tris‐(3,5‐dimethylphenyl‐carbamate) (Hägele et al, 2020). This method was applicable to authentic specimens such as in the identification of N ‐ethylpentylone in a sample suspected to be 3‐MMC (Hägele et al, 2020).…”

“…An example is the reported separation of 49 cathinones using a LC with diode‐array detection, employing a chiral stationary phase with cellulose tris‐(3,5‐dimethylphenyl‐carbamate) (Hägele et al, 2020). This method was applicable to authentic specimens such as in the identification of N ‐ethylpentylone in a sample suspected to be 3‐MMC (Hägele et al, 2020). Another method used LC‐UV employing a cellulose tris(3‐chloro‐4‐methylphenylcarbamate) chiral stationary phase was shown able to separate 17 cathinones and a partial resolution of only 2 cathinones was achieved (Taschwer et al, 2017).…”

Evaluation of cyclodextrin‐ and cyclofructan‐based chiral selectors for the enantioseparation of psychoactive substances in capillary electrophoresis

“…Extensive research has, so far, been performed on the enantioseparation of NPS-related compounds, mainly synthetic cathinone derivatives. In order to achieve chiral separation, different analytical methods, including chromatographic (high-performance liquid chromatography [14][15][16][17][18][19][20][21][22] and gas chromatography [11,16,23,24]), and electrophoretic methods (capillary electrophoresis [CE] and capillary electrochromatography [9,11,16,[25][26][27][28][29][30][31]) have been developed. Although chromatographic methods represent the foremost methods for enantiomeric separation, CE is considered to be an ideal technique for achieving chiral separations.…”

Analytical Separation of Closantel Enantiomers by HPLC

“…Therefore, there has been a widespread interest in chiral drugs separation and analysis in the pharmaceutical industry. In addition, numerous scientific research has focused on developing effective chromatographic methods for separating the racemic drugs [6][7][8][9] High-performance liquid chromatography (HPLC) is an ideal tool for chiral drugs separation and analysis due to its inherent accuracy, specificity, and versatility. The optimization process of the chromatographic condition is time-consuming, owing to the influences of many factors such as the composition of the mobile phase [10], structure of the chiral stationary phase (CSP) [11], and the column temperature [12].…”

“…Therefore, there has been a widespread interest in chiral drugs separation and analysis in the pharmaceutical industry. In addition, numerous scientific research has focused on developing effective chromatographic methods for separating the racemic drugs [ 6 , 7 , 8 , 9 ]…”