Analytical characterization and differentiation between threo- and erythro-4-fluoroethylphenidate.

IF 2.8 4区医学 Q2 TOXICOLOGY Forensic Toxicology Pub Date : 2023-07-01 Epub Date: 2023-04-25 DOI:10.1007/s11419-023-00664-y

Miho Sakamoto, Toshinari Suzuki, Daisuke Teraoka, Kazue Tanaka, Yuki Saeki, Kiyoko Kishimoto, Machiko Nagashima, Jun'ichi Nakajima, Jin Suzuki, Akiko Inomata, Takako Moriyasu, Haruhiko Fukaya

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Abstract

Purpose: Methylphenidate analogs appeared on the drug market during the last years. Its analogs contain two chiral centers and, thus, have potential varying configurations (i.e., threo and erythro forms). This study presents the analytical characterization of 4-fluoroethylphenidate (4-FEP) and its differentiation between threo- and erythro-4-FEP.

Methods: Analysis of the samples included high-performance liquid chromatography (HPLC), gas chromatography-electron ionization-mass spectrometry (GC-EI-MS), high-resolution mass spectrometry (HRMS) analyses, nuclear magnetic resonance (NMR) spectroscopy and X-ray crystal structure analysis.

Results: NMR spectroscopic investigations confirmed the differences between threo- and erythro-4-FEP, and demonstrated that both isomers could be separated using HPLC and GC methods. Two samples obtained from one vendor in 2019 consisted of threo-4-FEP, whereas the other two samples obtained from a different vendor in 2020 consisted of a mixture of threo- and erythro-4-FEP.

Conclusions: Several analytical approaches including HPLC, GC-EI-MS, HRMS analyses, NMR spectroscopy and X-ray crystal structure analysis enabled the unambiguous identification of threo- and erythro-4-FEP. The analytical data presented in this article will be useful for identifying threo- and erythro-4-FEP included in illicit products.

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分析表征和区分硫代和赤藓-4-氟乙基哌啶。

目的：哌醋甲酯类似物在最近几年出现在药品市场上。哌醋甲酯类似物含有两个手性中心，因此可能具有不同的构型（即threo和erythro形式）。本研究介绍了 4-氟乙基哌啶甲酯（4-FEP）的分析特性，以及对 4-氟乙基哌啶甲酯（4-FEP）进行区分的方法：样品分析包括高效液相色谱法（HPLC）、气相色谱-电离质谱法（GC-EI-MS）、高分辨质谱法（HRMS）分析、核磁共振（NMR）光谱法和 X 射线晶体结构分析：结果：核磁共振光谱研究证实了赤藓-4-FEP 和赤藓-4-FEP 之间的差异，并证明这两种异构体可通过 HPLC 和 GC 方法进行分离。2019 年从一家供应商处获得的两个样品由苏式-4-氟EP 组成，而 2020 年从另一家供应商处获得的另外两个样品则由苏式-4-氟EP 和赤式-4-氟EP 混合物组成：包括 HPLC、GC-EI-MS、HRMS 分析、NMR 光谱和 X 射线晶体结构分析在内的几种分析方法，使我们能够明确地识别苏-4-EP 和赤-4-EP。本文提供的分析数据将有助于鉴别非法产品中的硫代和赤式-4-FEP。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Forensic Toxicology TOXICOLOGY-

CiteScore

5.80

自引率

9.10%

发文量

审稿时长

3 months

期刊介绍： The journal Forensic Toxicology provides an international forum for publication of studies on toxic substances, drugs of abuse, doping agents, chemical warfare agents, and their metabolisms and analyses, which are related to laws and ethics. It includes original articles, reviews, mini-reviews, short communications, and case reports. Although a major focus of the journal is on the development or improvement of analytical methods for the above-mentioned chemicals in human matrices, appropriate studies with animal experiments are also published. Forensic Toxicology is the official publication of the Japanese Association of Forensic Toxicology (JAFT) and is the continuation of the Japanese Journal of Forensic Toxicology (ISSN 0915-9606).