- Successful use of a novel lux i-Amylose-1 chiral column for enantioseparation of “legal highs” by HPLC
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Bath salts, fumigations, cleaners and air fresheners, behind these terms substances are hidden, which count as “Legal Highs”. These fancy names are used to pretend Legal Highs as harmless compounds, to circumvent legal regulations for marketing as well as to increase the sales. Besides classic illicit drugs of synthetic origin such as amphetamines, cocaine and MDMA, the trade of these compounds, also known as new psychoactive substances (NPS), is not uncommon today. In many countries, NPS are still not subject to drug control. Among them, there are stimulants such as new amphetamine derivatives or cathinones, which possess a chiral centre. Little is known about the fact that the two possible enantiomers may differ in their pharmacological effect. The aim of this study was to test a novel HPLC column for the enantioseparation of a set of 112 NPS coming from different chemical groups and collected by internet purchases during the years 2010–2018. The CSP, namely Lux 5?μm i-Amylose-1, LC Column 250 x 4.6?mm, was run in normal phase mode under isocratic conditions, UV detection was performed at 245?nm and 230?nm, injection volume was 10?μl and flow rate was 1?ml/min. With a mobile phase consisting of n-hexane/isopropanol/diethylamine (90:10:0.1), herein, 79 NPS were resolved into their enantiomers successfully, for 37 of them baseline resolution was achieved. After increase of lipophily of the mobile phase to 99:1:0.1, another 27 compounds were baseline separated. It was found that all separated NPS are traded as racemic compounds.
- Kadkhodaei, Kian,Kadisch, Marlene,Schmid, Martin G.
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- Synthesis method of chiral compound
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The invention belongs to the technical field of chemical synthesis, and relates to a synthetic method of a chiral compound, in particular to a synthetic method of (1R, 2S)-1-phenyl-2-(pyrrolidine-1-yl) propan-1-ol. According to an ingenious synthesis strategy, asymmetric reduction can be realized during carbonyl reduction, and a target compound can be directly obtained at high yield. The problem that a target compound cannot be obtained at high yield through asymmetric reduction in the prior art is solved. Moreover, the synthesis of a high-purity compound (A) can be realized by using cheap hydrochloric acid and zinc chloride; in addition, no isomer is wasted; and according to the method, the use of norephedrine controlled product is avoided; the raw materials are cheap and easy to obtain,so that the synthesis cost is reduced; moreover, the preparation method disclosed by the invention is easy for industrial large-scale production.
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Paragraph 0151-0152
(2020/01/25)
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- A (S)- N - methoxy - methyl -2 - (tetrahydro-pyrrolyl) propionamide and its preparation method and application
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The invention discloses a (S)-N-methoxy-methyl-2-(pyrrolidine) propionamide shown as a formula (5). A preparation method is as follows: subjecting a starting material L-alanine to amino protection, reaction with N,O-dimethyl hydroxylamine hydrochloride, removal of amino protecting group, and alkylation; and subjecting the prepared compound shown as (5) to addition elimination and reduction to obtain an Efavirenz chiral ligand shown as the formula (7). The synthetic method of Efavirenz chiral ligand provided by the invention has the advantages of mild reaction conditions, simple operation, high yield and low production cost, and is suitable for industrialized production.
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Paragraph 0049; 0050
(2017/08/25)
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- Isolation and structural determination of non-racemic tertiary cathinone derivatives
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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.
- Zhou,Bouazzaoui,Jones,Goodrich,Bell,Sheldrake,Horton,Coles,Fletcher
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p. 9629 - 9636
(2015/09/28)
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- Chiral separation of cathinone and amphetamine derivatives by HPLC/UV using sulfated β-cyclodextrin as chiral mobile phase additive
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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 β-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 β-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. Copyright
- Taschwer, Magdalena,Seidl, Yvonne,Mohr, Stefan,Schmid, Martin G.
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p. 411 - 418
(2014/08/05)
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