PurposeCurrently, among new psychoactive substances, cathinone derivatives constitute the biggest group, which are mainly classified into N-alkylated, 3,4-methylenedioxy-N-alkylated, N-pyrrolidinyl, and 3,4-methylenedioxy-N-pyrrolidinyl derivatives. These derivatives are actively being subjected to minor modifications at the alkyl chains or the aromatic ring to create new synthetic cathinones with the goal of circumventing laws. In this review, the new synthetic cathinones that have appeared on the illegal drug market during the period 2014–2017 are highlighted, and their characterization by gas chromatography–mass spectrometry and liquid chromatography–tandem mass spectrometry is presented.MethodsVarious key words were used to conduct an extensive literature search across a number of databases, specifically for synthetic cathinones that emerged between 2014 and 2017.ResultsMore than 30 new cathinone derivatives were discovered. The preexisting parental compounds for the new derivatives are also referenced, and their mass spectral data are compiled in a table to facilitate their identification by forensic toxicologists.ConclusionsTo our knowledge, this is the most current review presenting new synthetic cathinones. Political authorities should take measures to implement and enforce generic scheduling (comprehensive system) laws to control the diversely modified synthetic cathinones. Supplementing the existing databases with new findings can greatly facilitate the efforts of forensic toxicologists.
Twenty species of Salvia, naturally grown or cultivated in Poland, are investigated by headspace gas chromatography-mass spectrometry analysis. The main components of the volatile fraction of Salvia species are identified as alpha-pinene, camphene, beta-pinene, thujol, camphor, beta-chamigrene, and cadina-3,9-diene. There are also the compounds that can be considered as chemotaxonomic markers, namely beta-myrcene for Salvia lavadulifolia, beta-phelandrene for Salvia verticillata, tau-terpinene for Salvia stepposa, and isocaryophyllene and caryophyllene for Salvia officinalis. Certain compounds (such as o-cymene present in Salvia canariensis and Salvia stepposa; beta-trans-ocymene present in Salvia lavadulifolia, Salvia sclarea, and Salvia amplexicaulis; thujenone present in Salvia staminea, Salvia atropatana, Salvia jurisicii, and Salvia officinalis; and thujone present in Salvia azurea, Salvia lavandulifolia, Salvia hians, and Salvia triloba) can constitute chemotaxonomic advice for the aforementioned species. Also, the lack of certain compounds otherwise common in the individual sage species can be considered as chemotaxonomic advice (e.g., Salvia sclarea has no alpha-pinene and beta-pinene; Salvia lavadulifolia lacks camphene; Salvia triloba lacks beta-pinene and camphene; and Salvia officinalis lacks beta-chamigrene, thujol, and cadina-3,9-diene).
In vitro and in vivo studies of the health and nutritional properties of durian (Durio zibethinus Murr.) were compared with snake fruit (Salacca edulis Reinw.) and mangosteen (Garcinia mangostana). Dietary fibers, minerals, and trace metals were comparable. Total polyphenols (mg of GAE/100 g of FW) and flavonoids (85.1+/-6.1) were significantly higher (p<0.05) than in snake fruit (217.1+/-13.2 (mg of CE/100 g of FW)), durian (309.7+/-19.3 and 61.2+/-4.9), and mangosteen (190.3+/-12.1 and 54.1+/-3.8). Antioxidant activity (microM TE/100 g of FW) of durian measured by DPPH and ABTS assays (228.2+/-13.4 and 2016.3+/-81.1) was significantly higher (p<0.05) than in snake fruit (110.4+/-7.9 and 1507.5+/-70.1) and mangosteen (79.1+/-5.9 and 1268.6+/-62.3). HPLC/DAD analysis of durian (microg/100 g of FW) showed that quercetin (1214.23+/-116.7) was present at levels three times that of caffeic acid, and twice as high as p-coumaric and cinnamic acids. The correlation coefficients between the bioactive compounds of fruits and their antioxidant activities were high (R2=0.99). Male Wistar rats (25) were divided into five dietary groups: the control group was fed the basal diet (BD); in addition to BD, the cholesterol (Chol) group was supplemented with 1% of Chol; the diets of the Chol/Durian, Chol/Snake, and Chol/Mangosteen groups were supplemanted with 5% of these fruits, respectively. It was found that diets supplemented with durian, and to a lesser degree with snake fruit and mangosteen, significantly hindered the rise in plasma lipids and the decrease in antioxidant activity. The nutritional values were comparably high. In conclusion, it could be suggested that inclusion of studied tropical fruits, especially durian, in known disease-preventing diets could be beneficial.
In earlier studies, we showed that certain low-molecular-weight carboxylic acids (profens, amino acids, hydroxy acids) can undergo spontaneous in vitro chiral conversion accompanied by condensation to from oligomers, and we proposed two simple models to describe these processes. Here, we present the results of investigations using non-chiral high-performance liquid chromatography with diode array detector (HPLC-DAD) and mass spectrometry (MS) on the dynamics of peptidization of S-, R-, and rac-phenylglycine dissolved in 70% aqueous ethanol and stored for times up to one year. The experimental results demonstrate that peptidization of phenylglycine can occur in an oscillatory fashion. We also describe, and carry out simulations with, three models that capture key aspects of the oscillatory condensation and chiral conversion processes.
Abstract:In an earlier study, we obtained experimental evidence of the oscillatory transenantiomerization of selected profen drugs (e.g., S-(+)-ibuprofen, S-(+)-naproxen, and S-(+) and R-(−)-flurbiprofen) dissolved in aqueous, aqueous-organic, and purely organic liquid media. This process was apparently catalyzed by basic or amphiprotic environments and involved ketoenol tautomerism, and the self-organization of molecules in the solution via association of the carboxylic functional group of profens through hydrogen bonding to form mixed H-bonded associates with the remaining constituents of the solution. A model of the oscillatory transenantiomerization of profens was also developed by adapting an earlier oscillatory model, the Templator. Our new model comprises two linked Templators. The essence of the Templator model adapted to the oscillatory transenantiomerization of profens is the assumption that the H-bonded profen homodimer acts as a template, able to generate new dimers having the same steric configuration as their respective monomeric units.As profens belong to the class of 2-arylpropionic acids (2-APAs), we concluded that the phenomenon of oscillatory transenantiomerization may occur in other 2-APAs as well, among them those amino acids whose molecular structure can formally be derived from propionic acid. Thus, in this study, we Address correspondence to Teresa Kowalska, Institute of Chemistry, University of Silesia, 9 Szkolna Street, 40-006 Katowice, Poland. E-mail: kowalska@us.edu.pl Oscillatory Transenantiomerization of L--Phenylalanine 1987focus our attention on L--phenylalanine (LPA; one of the nine amino acids essential for humans). Using thin layer chromatography (TLC) and polarimetry, we demonstrate the ability of LPA to undergo oscillatory transenantiomerization analogous to that observed with profens. The selforganization of molecules in a 70% ethanol solution of LPA is confirmed with photographs taken in UV light ( = 254 nm). Finally, we propose a skeleton molecular mechanism for the transenantiomerization of LPA and simulate the oscillatory interconversion of its L and D forms with two linked Templators.
In earlier studies, we have collected experimental evidence (mostly from thin‐layer chromatography and polarimetry) on the spontaneous oscillatory in vitro chiral conversion of simple carboxylic acids dissolved in 70% aqueous ethanol. To elucidate this phenomenon, we developed a simple theoretical model of two linked Templators. Recently, we have obtained additional experimental evidence of the spontaneous condensation of chiral carboxylic acids, based on the biuret test (amino acids), high performance liquid chromatography, and 13C NMR spectroscopy (profens and hydroxy acids). We briefly describe our experimental results in the context of the existing literature and outline an improved theoretical model for these phenomena. Our system resembles in some respects the reported oscillatory condensation of organic silanols. Here, the key reaction is the formation of carboxylic acid‐derived enols. Finally, we discuss the importance of the oscillatory chiral conversion of simple carboxylic acids for biochemistry, pharmacology, and related life sciences. Copyright © 2010 John Wiley & Sons, Ltd.
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