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以磺丁基醚β-环糊精为手性选择剂添加到背景电解质中,通过毛细管电泳实现苯并呋喃类及其他新型精神活性化合物的对映体拆分。

Enantioseparation of benzofurys and other novel psychoactive compounds by CE and sulfobutylether β-cyclodextrin as chiral selector added to the BGE.

作者信息

Taschwer Magdalena, Hofer Manfred G, 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

Electrophoresis. 2014 Oct;35(19):2793-9. doi: 10.1002/elps.201400164. Epub 2014 Aug 8.

Abstract

The illicit drug market of psychoactive substances for human abuse is continuously expanding and developing. Besides already known substance classes like cathinones, amphetamines or synthetic cannabinoids, further derivatives such as benzofurys, thiophenes, and structural analogues of methylphenidate entered the global market recently. As many of these new compounds contain a stereogenic centre it is supposed that their isomers may differ in their pharmacological effects as it is the case with amphetamines or several chiral active pharmaceutical ingredients, for instance. In the course of this study, a method for the chiral separation of a set of 16 recreational drugs by CE was developed. The aim was to separate the analytes into their enantiomers at equal conditions within short time. Sulfobutylether β-cyclodextrin served as chiral selector in an aqueous ammonium acetate solution containing ACN. For method optimization, methedrone and ethylphenidate were used as model compounds to find the appropriate concentration of chiral selector. Moreover, the influence of the pH value on enantioseparation was tested. Fourteen or 16 mM sulfobutylether β-cyclodextrin, 50 mM ammonium acetate solution (pH 4.5) with 10% ACN were found to be optimal for enantioseparation of seven benzofurys, four cathinones, two diphenidines, ethylphenidate, methiopropamine, and thiothinone. Most of them were baseline resolved at migration times below 25 min.

摘要

供人滥用的精神活性物质非法药物市场正在不断扩大和发展。除了卡西酮、苯丙胺或合成大麻素等已知的物质类别外,苯并呋喃、噻吩和哌醋甲酯的结构类似物等进一步的衍生物最近也进入了全球市场。由于这些新化合物中的许多都含有一个手性中心,因此推测它们的异构体可能在药理作用上有所不同,例如苯丙胺或几种手性活性药物成分就是这种情况。在本研究过程中,开发了一种通过毛细管电泳对手性分离一组16种娱乐性药物的方法。目的是在短时间内将分析物在相同条件下分离成其对映体。磺丁基醚β-环糊精在含有乙腈的乙酸铵水溶液中用作手性选择剂。为了优化方法,使用甲氧麻黄酮和哌醋甲酯作为模型化合物来找到合适的手性选择剂浓度。此外,还测试了pH值对映体分离的影响。发现14或16 mM磺丁基醚β-环糊精、50 mM乙酸铵溶液(pH 4.5)与10%乙腈最适合七种苯并呋喃、四种卡西酮、两种二苯并哌啶、哌醋甲酯、甲硫丙胺和硫噻酮的对映体分离。它们中的大多数在迁移时间低于25分钟时实现基线分离。

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