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. 2023 Jul;41(2):272-286.
doi: 10.1007/s11419-023-00664-y. Epub 2023 Apr 25.

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

Miho Sakamoto  1 , Toshinari Suzuki  2 , Daisuke Teraoka  2 , Kazue Tanaka  2 , Yuki Saeki  2 , Kiyoko Kishimoto  2 , Machiko Nagashima  2 , Jun'ichi Nakajima  2 , Jin Suzuki  2 , Akiko Inomata  2 , Takako Moriyasu  2   3 , Haruhiko Fukaya  4
Affiliations
Free article

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

Miho Sakamoto et al. Forensic Toxicol. 2023 Jul.
Free article

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.

Keywords: 4-Fluoroethylphenidate (4-FEP); Methylphenidate analog; New psychoactive substance; Nuclear magnetic resonance spectroscopy; X-ray crystallography.

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