Screening approach, optimisation and scale-up for chiral liquid chromatography of cathinones

Perera, Ranmith; Abraham, Ijeoma; Gupta, Shradha; Kowalska, Patrycja; Lightsey, Danielle; Marathaki, Chrysoula; Singh, Nagendra; Lough, W. J.

doi:10.1016/j.chroma.2012.11.001

Cited by 40 publications

(24 citation statements)

References 18 publications

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“…They are normally obtained in a stable protonated solid form, generally assumed to be the chloride salt. These include using HPLC with either a chiral stationary phase [41][42][43][44] or a chiral additive to the eluent, 45 GC following chiral derivatization of the analyte, 30,42,[46][47][48] capillary electrophoresis, [49][50][51][52] and NMR spectroscopy using appropriate chiral auxiliaries. 3 Calculations have predicted the pK a to be in the range of 8.4 to 9.5, suggesting that these compounds remain protonated at physiological pH, and unlike the analogous amphetamine derivatives, it is predicted that the ketone group increases both the planarity of the compound, and the hydrophilicity so lowering their activity with respect to the parent amphetamine, being less likely to cross cell membranes.…”

Section: Introductionmentioning

confidence: 99%

Isolation and structural determination of non-racemic tertiary cathinone derivatives

et al. 2015

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The racemic tertiary cathinones N,N-dimethylcathinone (1), N,N-diethylcathinone (2) and 2-(1-pyrrolidinyl)-propiophenone (3) have been prepared in reasonable yield and characterized using NMR and mass spectroscopy. HPLC indicates that these compounds are isolated as the anticipated racemic mixture. These can then be co-crystallized with (+)-O,O′-di-p-toluoyl-D-tartaric, (+)-O,O′-dibenzoyl-D-tartaric and (−)-O,O′-dibenzoyl-L-tartaric acids giving the single enantiomers S and R respectively of 1, 2 and 3, in the presence of sodium hydroxide through a dynamic kinetic resolution. X-ray structural determination confirmed the enantioselectivity. The free amines could be obtained following basification and extraction. In methanol these are reasonably stable for the period of several hours, and their identity was confirmed by HPLC and CD spectroscopy.

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Section: Introductionmentioning

confidence: 99%

Isolation and structural determination of non-racemic tertiary cathinone derivatives

et al. 2015

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“…In the literature, there are some articles dealing with the determination and chiral separation of cathinone, amphetamine, and related substances by high‐performance liquid chromatography (HPLC), capillary electrophoresis (CE), and gas chromatography (GC) …”

Section: Introductionmentioning

confidence: 99%

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

et al. 2014

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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.

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“…Pure 4-methylmethcathinone enantiomers were prepared in a relatively large scale (2 mg on column) by Whelk-O1 HPLC analytical column (250 mm × 4.6 mm I.D.) [49]. Pure 3,4-methylenedioxypyrovalerone enantiomers were prepared by amylose tris-3,5-dimethylphenylcarbamate phase HPLC semi-preparative column (200 mm × 7.0 mm I.D.)…”

Section: Other Separation Methodsmentioning

confidence: 99%

Chiral and stable isotope analysis of synthetic cathinones

Tai

Morrison

2017

TrAC Trends in Analytical Chemistry

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In the past decade synthetic cathinones have appeared in drug markets worldwide. Chiral analysis can provide information on relative enantiomeric abundances of synthetic cathinones in their drug products, potentially giving a signature of these products and hence linking the products or excluding them from possible sources. Additionally, due to natural variations of relative stable isotopic abundances of elements, stable isotope analysis of synthetic cathinone drug products provides the stable isotopic signature of the products and hence also has potential to provide additional information for the purpose of drug intelligence. Therefore, both molecular (chirality) and physicochemical (relative stable isotopic abundances) properties are important for forensic chemists to investigate. Chiral and isotope ratio mass spectrometric analysis are becoming increasingly important to forensic chemists and therefore this review will focus on an overview of these techniques applied to the synthetic cathinones.

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Screening approach, optimisation and scale-up for chiral liquid chromatography of cathinones

Cited by 40 publications

References 18 publications

Isolation and structural determination of non-racemic tertiary cathinone derivatives

Isolation and structural determination of non-racemic tertiary cathinone derivatives

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

Chiral and stable isotope analysis of synthetic cathinones

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