Abstract The demand for narcotics is still rising in societies worldwide and designer drugs, new psychoactive substances, (NPS) such as chiral cathinones, play an increasing role in a market. Since the psychoactive properties of their enantiomers may differ substantially in biological activity, there is an urgent need for simple unambiguous method of assessment of their enantiomer composition, which is not yet published. Here we propose a simple NMR methodology of chiral discrimination for several cathinones using R-BINOL as CSA (chiral solvating agent). The distinct differences are observed in 1H, 13C and NOESY spectra of solvation complexes of both enantiomers of mephedrone with R-BINOL. Due to these large differences in chemical shifts, if unequal population of the enantiomers are found, the limit of detection can be on the level of 13C satellite lines (0.55% of a major enantiomer) and their relative intensity can be validated by the integral comparison of a minor form with that of a satellite line of a major form. The methodology of the absolute stereochemistry of enantiomers is also proposed basing on observed differences in kinetics of solvation shifts and NOESY effects in both diastereromers. The computed structures of both solvation complexes are discussed. It helps validation of the assessment of the absolute configuration of both enantiomers.

中文翻译：

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卡西酮 - 使用 R-BINOL 进行对映异构体鉴别及其绝对立体化学分配的常规 NMR 方法

摘要 全世界社会对麻醉品的需求仍在不断增长，而设计药物、新型精神活性物质 (NPS)（如手性卡西酮）在市场中的作用越来越大。由于它们的对映异构体的精神活性性质可能在生物活性上存在很大差异，因此迫切需要一种简单明确的方法来评估它们的对映异构体组成，该方法尚未发表。在这里，我们提出了一种使用 R-BINOL 作为 CSA（手性溶剂化剂）对几种卡西酮进行手性鉴别的简单 NMR 方法。在甲氧麻黄酮与 R-BINOL 的两种对映异构体的溶剂化复合物的 1H、13C 和 NOESY 光谱中观察到明显差异。由于化学位移的这些巨大差异，如果发现对映异构体的数量不等，检测限可以在 13C 卫星线水平（主要对映体的 0.55%），它们的相对强度可以通过次要形式与主要形式的卫星线的积分比较来验证。对映异构体的绝对立体化学的方法也基于观察到的两种非对映异构体中溶剂化转变动力学和 NOESY 效应的差异。讨论了两种溶剂化复合物的计算结构。它有助于验证对两种对映异构体的绝对构型的评估。对映异构体的绝对立体化学的方法也基于观察到的两种非对映异构体中溶剂化转变动力学和 NOESY 效应的差异。讨论了两种溶剂化复合物的计算结构。它有助于验证对两种对映异构体的绝对构型的评估。对映异构体的绝对立体化学的方法也基于观察到的两种非对映异构体中溶剂化转变动力学和 NOESY 效应的差异。讨论了两种溶剂化复合物的计算结构。它有助于验证对两种对映异构体的绝对构型的评估。