Universität zu Köln

Klare, Helge, Neudoerfl, Joerg M., Brandt, Simon D., Mischler, Elisabeth, Meier-Giebing, Sigrid, Deluweit, Kathrin, Westphal, Folker and Laussmann, Tim ORCID: 0000-0002-0180-3513 (2017). Analysis of six 'neuro-enhancing' phenidate analogs. Drug Test. Anal., 9 (3). S. 423 - 436. HOBOKEN: WILEY. ISSN 1942-7611

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Abstract

Six collected phenidates, i.e., 4-methylmethylphenidate, 3,4-dichloromethylphenidate, ethylphenidate, 3,4-dichloroethylphenidate, ethylnaphthidate, and N-benzyl-ethylphenidate were fully characterized by means of X-ray, nuclear magnetic resonance (NMR), gas chromatography-mass spectrometry (GC-MS), electrospray ionization-tandem mass spectrometry (ESI-MS/MS), attenuated total reflectance Fourier transform infrared (ATR-FTIR) and GC solid-state IR analysis. Crystallography revealed the exclusive presence of the threo-configuration. Steric crowding induced by N-benzyl substitution at the piperidine moiety prompted an adoption of an unexpected axial positioning of substituents on the piperidine moiety in the crystal state as opposed to the exclusive equatorial positioning encountered in N-unsubstituted phenidate analogues. Gas phase computations of the relative lowest energy conformers confirm that the axial positioning appears to be favoured over the equatorial positioning; in solution, however, equatorial positioning is predominant according to nuclear Overhauser effect experiments. All samples, mainly originating from China, had a good to very good degree of purity indicative of their professional chemical synthesis. Routine analysis of these drugs by GC-MS revealed thermal decomposition of phenidate analogues in the injection port and/or on column to 2-aryl-ethyl-acetates and 2,3,4,5-tetrahydropyridines. The decomposition pathway was suggested to proceed via a 6-membered transition state which was supported by density functional theory (DFT) computations. Fragmentation pathways of decomposition products as well as the corresponding electron ionization (EI) mass spectra are provided. The thermal instability might thus render smoking or vaping' of these drugs a less effective route of administration. The analytical fingerprints of six structurally diverse phenidate analogues provide a helpful reference to forensic chemists in charge of identifying new psychoactive substances. Copyright (C) 2017 John Wiley & Sons, Ltd.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Klare, Helge UNSPECIFIED UNSPECIFIED UNSPECIFIED Neudoerfl, Joerg M. UNSPECIFIED UNSPECIFIED UNSPECIFIED Brandt, Simon D. UNSPECIFIED UNSPECIFIED UNSPECIFIED Mischler, Elisabeth UNSPECIFIED UNSPECIFIED UNSPECIFIED Meier-Giebing, Sigrid UNSPECIFIED UNSPECIFIED UNSPECIFIED Deluweit, Kathrin UNSPECIFIED UNSPECIFIED UNSPECIFIED Westphal, Folker UNSPECIFIED UNSPECIFIED UNSPECIFIED Laussmann, Tim UNSPECIFIED orcid.org/0000-0002-0180-3513 UNSPECIFIED
URN:	urn:nbn:de:hbz:38-237559
DOI:	10.1002/dta.2161
Journal or Publication Title:	Drug Test. Anal.
Volume:	9
Number:	3
Page Range:	S. 423 - 436
Date:	2017
Publisher:	WILEY
Place of Publication:	HOBOKEN
ISSN:	1942-7611
Language:	English
Faculty:	Unspecified
Divisions:	Unspecified
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language DISTRIBUTED DESIGNER DRUGS; NNEI INDAZOLE ANALOG; TRANSESTERIFICATION METABOLITE; PSYCHOACTIVE SUBSTANCES; ALPHA-PHPP; BASIS-SETS; ETHYLPHENIDATE; METHYLPHENIDATE; 5-CHLORO-NNEI; PHARMACOLOGY Multiple languages Biochemical Research Methods; Chemistry, Analytical; Pharmacology & Pharmacy Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/23755