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1.
Chirality ; 32(9): 1191-1207, 2020 09.
Artigo em Inglês | MEDLINE | ID: mdl-32671883

RESUMO

Besides the abuse of well-known illicit drugs, consumers discovered new synthetic compounds with similar effects but minor alterations in their chemical structure. Originally, these so-called novel psychoactive substances (NPS) have been created to circumvent law of prosecution because of illicit drug abuse. During the past decade, such compounds came up in generations, the most popular compound was a synthetic cathinone derivative named mephedrone. Cathinones are structurally related to amphetamines; to date, more than 120 completely new derivatives have been synthesized and are traded via the Internet. Cathinones possess a chiral center; however, only little is known about the pharmacology of their enantiomers. However, NPS comprise further chiral compound classes such as amphetamine derivatives, ketamines, 2-(aminopropyl)benzofurans, and phenidines. In continuation of our project, a cheap and easy-to-perform chiral capillary zone electrophoresis method for enantioseparation of cathinones presented previously was extended to the aforementioned compound classes. Enantioresolution was achieved by simply adding native ß-cyclodextrin, acetyl-ß-cyclodextrin, 2-hydroxypropyl-ß-cyclodextrin, or carboxymethyl-ß-cyclodextrin as chiral selector additives to the background electrolyte. Fifty-one chiral NPS served as analytes mainly purchased from online vendors via the Internet. Using 10 mM of the aforementioned ß-cyclodextrins in a 10 mM sodium phosphate buffer (pH 2.5), overall, 50 of 51 NPS were resolved. However, chiral separation ability of the selectors differed depending on the analyte. Additionally, simultaneous enantioseparations, the determination of enantiomeric migration orders of selected analytes, and a repeatability study were performed successfully. It was proven that all separated NPS were traded as racemic mixtures.


Assuntos
Eletroforese Capilar , Psicotrópicos/química , beta-Ciclodextrinas/química , Psicotrópicos/isolamento & purificação , Estereoisomerismo
2.
Electrophoresis ; 40(14): 1787-1794, 2019 07.
Artigo em Inglês | MEDLINE | ID: mdl-31141181

RESUMO

In the past decade, more than 100 different cathinone derivatives slopped over entire Europe due to their enormous popularity. Generally, these novel psychoactive substances are easily available via the internet. This fact leads to various social problems, since cathinones are substances with consciousness-changing effects and are mainly misused for recreational matters by their consumers. Cathinones possess a chiral center including two enantiomeric forms with potentially different pharmacological behavior. This fact makes analytical method development regarding their chiral separation indispensable. In this study, a chiral capillary zone electrophoresis method for the enantioseparation of 61 cathinone and pyrovalerone derivatives was developed by means of four different ß-cyclodextrin derivatives. As chiral selectors, native ß-cyclodextrin as well as three of its derivatives namely acetyl-ß-cyclodextrin, 2-hydroxypropyl-ß-cyclodextrin, and carboxymethyl-ß-cyclodextrin were used. The cathinone and pyrovalerone derivatives were either purchased in internet stores or seized by police. As a result, overall 58 of 61 studied substances were partially or baseline separated by at least one of the four chiral selectors using 10 mM of ß-cyclodextrin derivative in a 10 mM sodium phosphate buffer (pH 2.5). Furthermore, the method was found to be suitable for simultaneous enantioseparations, for enantiomeric purity checks and to differentiate between positional isomers. Moreover, an intra- and an interday validation was performed successfully for each chiral selector to prove the robustness of the method.


Assuntos
Alcaloides/isolamento & purificação , Eletroforese Capilar , beta-Ciclodextrinas/química , 2-Hidroxipropil-beta-Ciclodextrina/química , Pirrolidinas/isolamento & purificação , Estereoisomerismo
3.
Chirality ; 2018 Jun 19.
Artigo em Inglês | MEDLINE | ID: mdl-29920777

RESUMO

In the recent years, hundreds of Novel Psychoactive Substances (NPS) have entered both the European and the global drug market. These drugs, which are mainly used for recreational matters, have caused serious social problems. Every year, the spectrum of these misused drugs is enlarged by new derivatives, which are produced by modifications of basic structures of already well-known substances. Additionally, a lot of them possess a stereogenic center which leads to 2 enantiomeric forms. The fact that the pharmacological effects and potencies of the enantiomers of these chiral NPS may differ can be assumed from a broad spectrum of active pharmaceutical ingredients. For this reason, analytical method development regarding enantiomeric separation for these classes of substances is of great pharmaceutical and medical interest. The aim of this work was to create an easy-to-prepare chiral capillary electrophoresis method for the enantioseparation of NPS which contains a primary amino group by means of (+)-18-crown-6-tetracarboxylic acid as chiral selector. Novel Psychoactive Substances were purchased at various Internet stores or represent samples seized by Austrian police. The effects of selector concentration, the electrolyte composition, and the addition of organic modifiers to the background electrolyte on enantioseparation were investigated. Under optimized conditions, the use of 20-mM (+)-18-crown-6-tetracarboxylic acid, 10-mM Tris, and 30-mM citric acid buffer at pH 2.10 turned out to be effective. Fifteen of 24 tested NPS were resolved in their enantiomers within 15 minutes. It was found that all NPS were traded as racemic mixtures.

4.
J Chromatogr A ; 1624: 461256, 2020 Aug 02.
Artigo em Inglês | MEDLINE | ID: mdl-32540082

RESUMO

Novel Psychoactive Substances (NPS) represent an alternative to established illicit drugs. They are traded via the internet and exhibit small alterations in their chemical structure to circumvent law, however, their psychotropic effects are comparable. There is still poor knowledge about side effects and health risks. By the end of 2018, 730 NPS were reported to EMCDDA (European Monitoring Centre for Drugs and Drug Addiction). Among different compound classes, many NPS are chiral and few publications deal with the different pharmacological and toxicological properties of their pure enantiomers. Therefore, analytical method development concerning enantioseparation of NPS is of great interest. Chiral separation protocols of established illicit drugs have been transferred for NPS, selected examples are given as well. Different methods for enantioseparation of NPS comprising mainly stimulating drugs such as cathinones, pyrovalerones, amphetamines, ketamines, (2-aminopropyl) benzofuranes, phenidines, phenidates, morpholines and thiophenes are reviewed. Moreover, chiral resolution of some cannabinomimetics by HPLC is presented. Chromatographic and electrophoretic techniques such as GC, HPLC, SFC, CE and CEC are discussed and in some cases compared. Mainly, solid samples either purchased from internet vendors, seized by police or collected from patients in hospitals are subject to analysis. Chiral selectors used for HPLC are listed in a Table. It was shown that particularly stimulating drugs are traded as racemic mixtures, which is not the case with cannabinomimetics. Mainly, HPLC and CE were used for enantioseparation of NPS.


Assuntos
Cromatografia/métodos , Eletroforese/métodos , Psicotrópicos/química , Psicotrópicos/isolamento & purificação , Humanos , Estereoisomerismo
5.
J Pharm Biomed Anal ; 179: 112967, 2020 Feb 05.
Artigo em Inglês | MEDLINE | ID: mdl-31732403

RESUMO

The abuse of Novel Psychoactive Substances (NPS) still cause severe problems. A lot of them contain a stereogenic centre which leads to possible different pharmacological effects of the enantiomers. The aim of this study was to establish an enantioselective HPLC-UV method with applicability to a broad spectrum of NPS. Different compound classes including mainly amphetamines, cathinones, ketamines, pyrovalerones and benzofuries were tested for successful enantioseparation by one common chromatographic condition. All NPS samples were bought in various internet stores, were sythesized inhouse or were seized by the Austrian police. A commercially available Phenomenex LUX® AMP 3 µm, 150 × 4,6 mm column served as chiral stationary phase (CSP) for the enantiomeric separation experiments. This CSP has been developed particularly for enantioresolution of high abundant synthetic chiral drugs such as MDMA and amphetamine. All measurements were performed under isocratic conditions. For method optimisation, the effects of different mobile phase compositions, different pH values and temperatures on enantioseparation were investigated. Final mobile phase consisted of ammonium bicarbonate solution (5 mM) adjusted with concentrated ammonia to a pH of 11.3 mixed with acetonitrile in a ratio of 70:30. All in all, 83 of 95 analysed NPS were separated in their enantiomers successfully within 40 min. Furthermore, the method was found to be suitable for simultaneous enantioseparations, for enantiomeric elution order determinations, enantiomeric purity checks and for positional isomer separations. To prove the repeatability of the method, an intra- and an interday validation was performed successfully. By means of the wide applicability of the chosen column all separated NPS were shown to be traded as racemic mixtures.


Assuntos
Cromatografia Líquida de Alta Pressão/métodos , Drogas Ilícitas/análise , Psicotrópicos/análise , Concentração de Íons de Hidrogênio , Drogas Ilícitas/química , Psicotrópicos/química , Estereoisomerismo , Temperatura
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