Chiral Separation of Cathinone and Amphetamine Derivatives by HPLC/UV Using Sulfated β-Cyclodextrin as Chiral Mobile Phase Additive

被引:55
作者
Taschwer, Magdalena [1 ]
Seidl, Yvonne [1 ]
Mohr, Stefan [1 ,2 ]
Schmid, Martin G. [1 ]
机构
[1] Karl Franzens Univ Graz, Inst Pharmaceut Sci, Dept Pharmaceut Chem, A-8010 Graz, Austria
[2] Res Ctr Pharmaceut Engn, Graz, Austria
关键词
cathinone; amphetamine; chiral separation; sulfated beta-cyclodextrin; ALPHA-AMINO KETONES; CAPILLARY-ELECTROPHORESIS; STATIONARY-PHASE; ENANTIOMERIC SEPARATION; LIQUID-CHROMATOGRAPHY; RECREATIONAL DRUGS; MASS-SPECTROMETRY; DESIGNER DRUGS; METHAMPHETAMINE; DERIVATIZATION;
D O I
10.1002/chir.22341
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
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 m served as the stationary phase. The chiral mobile phase consisted of methanol, water, and sulfated beta-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 beta-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. (C) 2014 Wiley Periodicals, Inc.
引用
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页码:411 / 418
页数:8
相关论文
共 23 条
[1]  
AboulEnein HY, 1997, BIOMED CHROMATOGR, V11, P7, DOI 10.1002/(SICI)1099-0801(199701)11:1<7::AID-BMC607>3.0.CO
[2]  
2-F
[3]  
AboulEnein HY, 1997, BIOMED CHROMATOGR, V11, P47, DOI 10.1002/(SICI)1099-0801(199701)11:1<47::AID-BMC626>3.0.CO
[4]  
2-M
[5]   Enantiomeric Separation of 13 New Amphetamine-Like Designer Drugs by Capillary Electrophoresis, Using Modified--Cyclodextrins [J].
Burrai, Lucia ;
Nieddu, Maria ;
Pirisi, Maria Antonietta ;
Carta, Antonio ;
Briguglio, Irene ;
Boatto, Gianpiero .
CHIRALITY, 2013, 25 (10) :617-621
[6]   Liquid chromatographic direct resolution of aryl α-amino ketones on a residual silanol group-protecting chiral stationary phase based on optically active (3,3′-diphenyl-1,1′-binaphthyl)-20-crown-6 [J].
Choi, Hee Jung ;
Jin, Jong Sung ;
Hyun, Myung Ho .
JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES, 2008, 875 (01) :102-107
[7]   Simultaneous Chiral Separation of Methylamphetamine and Common Precursors Using Gas Chromatography/Mass Spectrometry [J].
Drake, Samantha J. ;
Morrison, Calum ;
Smith, Frank .
CHIRALITY, 2011, 23 (08) :593-601
[8]  
EMCDDA, 2013, EU DRUG MARK REP
[9]   METHCATHINONE (CAT) - AN ENANTIOMERIC POTENCY COMPARISON [J].
GLENNON, RA ;
YOUNG, R ;
MARTIN, BR ;
DALCASON, TA .
PHARMACOLOGY BIOCHEMISTRY AND BEHAVIOR, 1995, 50 (04) :601-606
[10]   Chiral determination of amphetamine and related compounds using chloroformates for derivatization and high-performance liquid chromatography [J].
Herráez-Hernández, R ;
Campíns-Falcó, P ;
Tortajada-Genaro, LA .
ANALYST, 1998, 123 (10) :2131-2137