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使用硫酸化β-环糊精作为手性流动相添加剂,通过高效液相色谱/紫外检测法对手性卡西酮和苯丙胺衍生物进行手性分离。

Chiral separation of cathinone and amphetamine derivatives by HPLC/UV using sulfated ß-cyclodextrin as chiral mobile phase additive.

作者信息

Taschwer Magdalena, Seidl Yvonne, Mohr Stefan, Schmid Martin G

机构信息

Department of Pharmaceutical Chemistry, Institute of Pharmaceutical Sciences, Karl-Franzens-University Graz, Graz, Austria.

出版信息

Chirality. 2014 Aug;26(8):411-8. doi: 10.1002/chir.22341. Epub 2014 Jun 9.

Abstract

In the last years the identification of new legal and illegal highs has become a huge challenge for the police and prosecution authorities. In an analytical context, only a few analytical methods are available to identify these new substances. Moreover, many of these recreational drugs are chiral and it is supposed that the enantiomers differ in their pharmacological potency. Since nonenantioselective synthesis is easier and cheaper, they are mainly sold as racemic mixtures. The goal of this research work was to develop an inexpensive method for the chiral separation of cathinones and amphetamines. This should help to discover if the substances are sold as racemic mixtures and give further information about their quality as well as their origin. Chiral separation of a set of 6 amphetamine and 25 cathinone derivatives, mainly purchased from various Internet shops, is presented. A LiChrospher 100 RP-18e, 250 x 4 mm, 5 µm served as the stationary phase. The chiral mobile phase consisted of methanol, water, and sulfated ß-cyclodextrin. Measurements were performed under isocratic conditions in reversed phase mode using UV detection. Four model compounds of the two substance classes were used to optimize the mobile phase. Under final conditions (methanol:water 2.5:97.5 + 2% sulfated ß-cyclodextrin) enantiomers of amphetamine and five derivatives were baseline separated within 23 min. In all, 17 cathinones were completely or partially chirally separated. However, as only 3 of 25 cathinones were baseline resolved, the application of this method is limited for cathinone analogs. Additionally, the results were compared with an RP-8e column.

摘要

在过去几年中,识别新型合法和非法兴奋剂已成为警方和检察机关面临的巨大挑战。在分析层面,仅有少数分析方法可用于识别这些新物质。此外,许多这类消遣性药物是手性的,据推测其对映体在药理活性上存在差异。由于非对映选择性合成更简便且成本更低,它们主要以外消旋混合物的形式出售。本研究工作的目标是开发一种廉价的方法用于分离卡西酮和苯丙胺的对映体。这将有助于发现这些物质是否以外消旋混合物形式出售,并提供有关其质量及来源的更多信息。本文展示了对一组主要从各类网店购得的6种苯丙胺和25种卡西酮衍生物进行的手性分离。使用粒径为5 µm、规格为250×4 mm的LiChrospher 100 RP - 18e作为固定相。手性流动相由甲醇、水和硫酸化β - 环糊精组成。测量在反相模式的等度条件下进行,并采用紫外检测。使用这两类物质中的四种模型化合物来优化流动相。在最终条件(甲醇∶水 2.5∶97.5 + 2%硫酸化β - 环糊精)下,苯丙胺及其五种衍生物的对映体在23分钟内实现了基线分离。总共17种卡西酮实现了完全或部分手性分离。然而,由于25种卡西酮中只有3种实现了基线分离,该方法在卡西酮类似物的应用上存在局限性。此外,还将结果与RP - 8e柱的结果进行了比较。

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