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Advantages and Limitations of Spectroscopic, Chromatographic and Electrophoretic Methods for the Characterisation of Synthetic Cannabinoids and Synthetic

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Advantages and Limitations of Spectroscopic, Chromatographic and Electrophoretic Methods for the Characterisation of Synthetic Cannabinoids and Synthetic Advantages and limitations of spectroscopic, chromatographic and electrophoretic methods for the characterisation of synthetic cannabinoids and synthetic cathinone derivatives Dissertation der Mathematisch-Naturwissenschaftlichen Fakultät der Eberhard Karls Universität Tübingen zur Erlangung des Grades eines Doktors der Naturwissenschaften (Dr. rer. nat.) vorgelegt von Sonja Metternich aus Koblenz Tübingen 2020 Gedruckt mit Genehmigung der Mathematisch-Naturwissenschaftlichen Fakultät der Eberhard Karls Universität Tübingen. Tag der mündlichen Qualifikation: 08.06.2020 Dekan: Prof. Dr. Wolfgang Rosenstiel 1. Berichterstatter: Prof. Dr. Carolin Huhn 2. Berichterstatter: Prof. Dr. Jürgen Pomp Table of contents Table of contents Table of contents ......................................................................................................................... i Abstract ...................................................................................................................................... 3 Zusammenfassung ...................................................................................................................... 4 1 Introduction ............................................................................................................................. 5 1.1 New psychoactive substances - a never ending-story ................................................ 5 1.1.1 Synthetic cannabinoids ........................................................................................... 6 1.1.2 Synthetic cathinone derivatives .............................................................................. 8 1.2 NPS analytics - a challenging task in Forensic Science ............................................. 9 1.2.1 Presumptive tests .................................................................................................. 10 1.2.2 Optical spectroscopy ............................................................................................ 12 1.2.3 Separation Techniques ......................................................................................... 14 1.2.4 Chiral analysis ...................................................................................................... 15 2 Ion mobility spectrometry as a fast screening tool for synthetic cannabinoids to uncover drug trafficking in jail via herbal mixtures, paper, food, and cosmetics .................................. 17 2.1 Abstract .................................................................................................................... 17 2.2 Introduction .............................................................................................................. 17 2.3 Materials and Methods ............................................................................................. 21 2.3.1 Chemicals ............................................................................................................. 21 2.3.2 Methodology: Characterization of NPS powders from seizures .......................... 23 2.4 Results ...................................................................................................................... 27 2.4.1 Characterization of NPS with UPLC, GC-MS and NMR .................................... 27 2.4.2 IMS measurements ............................................................................................... 31 2.5 Discussion ................................................................................................................ 38 2.6 Conclusion ................................................................................................................ 40 3 Discrimination of synthetic cannabinoids in herbal matrices and of synthetic cathinone derivatives by portable and laboratory-based Raman spectroscopy ........................................ 41 3.1 Abstract .................................................................................................................... 41 3.2 Introduction .............................................................................................................. 41 3.3 Materials and Methods ............................................................................................. 43 3.3.1 Chemicals ............................................................................................................. 43 3.3.2 Methodology ........................................................................................................ 46 3.3.3 Data treatment and chemometrics ........................................................................ 48 3.4 Results and discussion .............................................................................................. 49 3.4.1 Comparison of different Raman spectrometers .................................................... 49 3.4.2 Principal Component Analysis ............................................................................. 53 3.4.3 Characteristic Raman bands for both, synthetic cathinone derivatives and synthetic cannabinoids ..................................................................................................... 56 3.4.4 Identification of synthetic cannabinoids in 60 herbal mixtures from casework samples ............................................................................................................................. 69 3.5 Conclusion ................................................................................................................ 73 4 Terahertz spectroscopy for the contactless and non-destructive detection of synthetic cannabinoids to uncover drug trafficking ................................................................................. 74 4.1 Abstract .................................................................................................................... 74 4.2 Introduction .............................................................................................................. 74 4.3 Materials and Methods ............................................................................................. 77 4.3.1 Chemicals ............................................................................................................. 77 i Table of contents 4.3.2 Methodology: Characterisation of NPS powders from seizures .......................... 78 4.4 Results ...................................................................................................................... 83 4.4.1 Characterisation of NPS with GC-MS and NMR ................................................ 83 4.4.2 THz procedure ...................................................................................................... 83 4.4.3 Model applications and matrix tolerance ............................................................. 91 4.5 Discussion ................................................................................................................ 94 4.6 Conclusion ................................................................................................................ 97 5 Structural similarity of synthetic cannabinoids in herbal mixtures allows to cross-calibrate analytes without reference material by UPLC-DAD ............................................................... 98 5.1 Abstract .................................................................................................................... 98 5.2 Introduction .............................................................................................................. 98 5.3 Materials and Methods ........................................................................................... 100 5.3.1 Chemicals ........................................................................................................... 100 5.3.2 Methodology ...................................................................................................... 103 5.4 Results and discussion ............................................................................................ 104 5.4.1 Characterisation of reference samples including NMR and GC-MS ................. 104 5.4.2 Evaluation of the UPLC-DAD method .............................................................. 105 5.4.3 Application to casework samples ....................................................................... 117 5.5 Conclusion .............................................................................................................. 119 6 Chiral discrimination of NPS using CE-DAD: Enantioselective separation of synthetic cathinone derivatives by capillary electrophoresis with UV .................................................. 120 6.1 Abstract .................................................................................................................. 120 6.2 Introduction ............................................................................................................ 120 6.3 Materials and Methods ........................................................................................... 123 6.3.1 Chemicals ........................................................................................................... 123 6.3.2 Methodology ...................................................................................................... 127 6.4 Results and discussion ............................................................................................ 128 6.4.1 Chiral separation optimisation ..........................................................................
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