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Determination of chiral amphetamine in seized tablets by indirect enantioseparation using GC–MS
Journal of King Saud University-Science ( IF 3.8 ) Pub Date : 2020-05-22 , DOI: 10.1016/j.jksus.2020.05.003
Abdulrhman M. Dhabbah

The illegal production of amphetamine and its derivatives has rapidly increased in the last years to provide the increasing demand all over the world. Since amphetamine is chiral, its enantiomers have different pharmacological activities. The present work aims to study the enantiomeric profile of amphetamine in several batches of tablets seized from the illegal market. The R and S antipodes were first converted to diastereomers by reaction with trifluoroacetyl-l-prolyl chloride (L-TPC) as chiral reagent. The obtained diastereomers were then full separated by gas chromatography with a resolution factor RS of 1.69, then characterized by mass spectrometry. Both S and R-amphetamine showed similar contents in all investigated samples, with a slight excess of the more active S eutomer. The calculated enantiomeric excess (ee%) values are all positive in the range 0.60–9.72%. The total concentration of amphetamine was from 36.44 to 96.22 mg/g in all tablets. The seized materials showed also the presence of some other ingredients used as additives in manufacturing the tablets such as caffeine, phenazocine, diphenhydramine, dibutyl phthalate and 9-octadecenamide. These findings confirmed that the synthesis of amphetamine used in these tablets was performed using inexpensive and achiral starting substances.



中文翻译:

使用GC–MS间接对映体分离法测定缉获片剂中的手性苯丙胺

近年来,苯丙胺及其衍生物的非法生产迅速增加,从而在世界范围内提供了日益增长的需求。由于苯丙胺是手性的,其对映异构体具有不同的药理活性。本工作旨在研究从非法市场缉获的几批片剂中苯丙胺的对映体特征。首先通过与三氟乙酰基-1-脯氨酰氯(L -TPC)作为手性试剂反应,将RS对映体转化为非对映异构体。然后将所得非对映异构体通过气相色谱以1.69的分离度R S进行完全分离,然后通过质谱进行表征。既小号ř-苯丙胺在所有研究的样品中均显示相似的含量,但活性较高的S eutomer略有过量。计算的对映体过量(ee%)值在0.60–9.72%的范围内均为正值。在所有片剂中,苯丙胺的总浓度为36.44至96.22 mg / g。查获的材料还显示出一些其他成分在制造片剂时用作添加剂,例如咖啡因,吩唑辛,苯海拉明,邻苯二甲酸二丁酯和9-十八烯酰胺。这些发现证实了在这些片剂中使用的苯丙胺的合成是使用廉价且非手性的起始物质进行的。

更新日期:2020-05-22
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