Chiral separation of new designer drugs (Cathinones) on chiral ion-exchange type stationary phases

Wolrab, Denise; Frühauf, Peter; Moulisová, Alena; Kuchař, Martin; Gerner, Christopher; Lindner, Wolfgang; Kohout, Michal

doi:10.1016/j.jpba.2015.12.023

Cited by 33 publications

(16 citation statements)

References 42 publications

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“…[31][32][33][34] Since the substance is available as hydrochloride, the polar organic mode arrangement with ethanol as the bulk mobile phase was assumed to provide the best results. [31][32][33][34] Since the substance is available as hydrochloride, the polar organic mode arrangement with ethanol as the bulk mobile phase was assumed to provide the best results.…”

Section: Enantioseparation Of Butylonementioning

confidence: 99%

“…Cathinones can generally be enantioseparated using various methods including liquid chromatography, gas chromatography, supercritical fluid chromatography, and capillary electrophoresis. [31][32][33][34] Since the substance is available as hydrochloride, the polar organic mode arrangement with ethanol as the bulk mobile phase was assumed to provide the best results. Although the enantioseparation of a series of cathinones in the polar organic mode has been reported recently, 35 butylone was not included in the study.…”

Section: Enantioseparation Of Butylonementioning

confidence: 99%

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Structure determination of butylone as a new psychoactive substance using chiroptical and vibrational spectroscopies

et al. 2018

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Recently, there has been a worldwide substantial increase in the consumption of new psychoactive substances (NPS), compounds that mimic the structure of illicit drugs, such as amphetamines or ecstasy. The producers try to avoid the law by a slight modification of illicit structures, thereby developing dozens of temporarily legal NPS every year. The current trends in the detection and monitoring of such substances demand a fast and reliable analysis. Molecular spectroscopy represents a highly effective tool for the identification of NPS and chiroptical methods can provide further information on their 3D structure, which is the key for the determination of their biological activity. We present the first systematic study of NPS, specifically butylone, combining chiroptical and vibrational spectroscopies with ab initio calculations. According to density functional theory calculations, 6 stable lowest energy conformers of butylone were found and their molecular structure was described. For each conformer, the relative abundance based on the Boltzmann distribution was estimated, their population weighted spectra predicted and compared to the experimental results. Very good agreement between the experimental and the simulated spectra was achieved, which allowed not only the assignment of the absolute configuration, but also a precise description of the molecular structure.

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Section: Enantioseparation Of Butylonementioning

confidence: 99%

Section: Enantioseparation Of Butylonementioning

confidence: 99%

Structure determination of butylone as a new psychoactive substance using chiroptical and vibrational spectroscopies

et al. 2018

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“…Furthermore immobilization reduces the amount of selector required. 79,80 Liquid-liquid contacting with supported liquids may be executed in various ways, for example thin layer extraction, [81][82][83][84][85] solvent impregnated resins, [86][87][88][89][90] or liquid membranes. In liquid membranes, the selectivity is not based on equilibrium partitioning, such as in ELLE, but on a difference in flux (see Fig.…”

Section: Mass Transfer In Liquid Membranesmentioning

confidence: 99%

Enantioseparation with liquid membranes

Gössi

Riedl

Schuur

2017

J of Chemical Tech & Biotech

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Chiral resolution of racemic products is a challenging and important task in the pharmaceutical, agrochemical, flavor, polymer and fragrances industries. One of the options for these challenging separations is to use liquid membranes. Although liquid membranes have been known for almost four decades and have been used for optical resolutions, no comprehensive review has been published about the use of this technology for enantioseparations. In this review, the various liquid membrane‐related technologies are described and compared, including bulk liquid membranes, emulsion liquid membranes, micelle‐extraction and micellar enhanced ultrafiltration, as well as supported liquid membranes. Next to technological advances, an overview of recent developments in chiral recognition chemistry in liquid–liquid equilibria is presented. The following extractant classes have recently been reported in conjunction with chiral separation: cyclodextrines, BINOL's, calixarenes, crown ethers, BINAP's, tartaric acids and ionic liquids. The use of two supported (non‐liquid) membranes with an inner loop of extract phase appears to be the most stable liquid membrane configuration, allowing for a large degree of freedom in operational conditions such as solvent to feed ratio. The library of solvents still needs broadening to make the technology more versatile and based on the variety of successes with catalytically active organometallic complexes, development of new chiral selector systems based on asymmetric catalysis literature is suggested for future selector screening studies. © 2017 Society of Chemical Industry

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“…Chiral ion exchange type phases have been investigated in the past year [44] and chemical structures of the applied phase moieties are shown in Fig. 5 (c).…”

Section: High Performance Liquid Chromatography (Hplc)mentioning

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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Chiral separation of new designer drugs (Cathinones) on chiral ion-exchange type stationary phases

Cited by 33 publications

References 42 publications

Structure determination of butylone as a new psychoactive substance using chiroptical and vibrational spectroscopies

Structure determination of butylone as a new psychoactive substance using chiroptical and vibrational spectroscopies

Enantioseparation with liquid membranes

Chiral and stable isotope analysis of synthetic cathinones

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