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The Application of Stable Isotope Ratio Mass Spectrometry to Illicit Drug Profiling

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The Application of Stable Isotope Ratio Mass Spectrometry to Illicit Drug Profiling The Application of Stable Isotope Ratio Mass Spectrometry to Illicit Drug Profiling The Application of Stable Ratio Isotope Mass Spectrometry to Illicit Drug Profiling Alexandra Jay Doddridge A thesis submitted for the fulfilment of the requirements for the degree of Master of Science (Research) University of Technology, Sydney 2016 Certificate of Original Ownership I certify that the work in this thesis has not previously been submitted for a degree nor has it been submitted as part of requirements for a degree except as fully acknowledged within the text. I also certify that the thesis has been written by me. Any help that I have received in my research work and the preparation of the thesis itself has been acknowledged. In addition, I certify that all information sources and literature used are indicated in the thesis. Signature of Student: Date ii Acknowledgements I owe the existence of the thesis to a number of key people and organisations who are listed below. Dr Philip Maynard, for the support and encouragement over the last three years. For always being at the other end of the computer and especially for the endless editing in the final moments before this thesis was complete. Dr Michael Collins who I thank for initially saying ‘yes’ and allowing me to undertake this study. Thank you for opening your laboratory to me and sharing your chemical knowledge. For birthing the idea of an isotopic study of synthetic cathinones and my first publication! Dr Helen Salouros who was my driving force and inspiration. Without your encouragement, I would have given up a thousand times over. Thank you for your advice, taking me under your wing and allowing me to create something that I am proud of. The National Measurement Institute, especially the ChemBio branch and Dr Lindsey Mackay for allowing me to utilise their facilities, for the supply of consumables and providing the financial support throughout this study. Without this support, this thesis would be non- existent. My colleagues at the Australian Forensic Drug Laboratory (AFDL) for putting up with me and welcoming me with open arms. Thank you for keeping me entertained, for your training in chemical analysis and continuing support. An even bigger thank you for making the endless hours spent weighing samples that little bit more bearable. The Chemical Reference Materials (CRM) Laboratory for the use and access to their lab. To the synthesis team for their knowledge and advice when reactions weren’t working. For the loan of equipment and use of chemicals in ‘emergencies’. Special mention to Dr Alamgir Mahiuddin for allowing me to take over his fume hood for hours on end. The Australian Federal Police and Australian Border Force, who I acknowledge and thank for the provision of samples used in this research. Family and friends who kept me sane, listened to my venting and provided that support in the outside world! Especially Dr Ellaine Munton who always had open ears and provided much appreciated editorial assistance. iii Table of Contents Certificate of Original Ownership ……………………….………………………………………………………………………ii Acknowledgements…………………………………………..……………………………………………………………………….iii List of Abbreviations….…….………………………………………………………………………………………………………..vii List of Figures……………………………………………………………………………………………………………………………..ix List of Tables………………………………………………………………………………………………………………………………xi Abstract……….……………………………………………………………………………………………………………………………xii Chapter 1: Introduction 1.1 Illicit Drug Overview .......................................................................................................... 1 1.2 Novel Psychoactive Substances ......................................................................................... 3 1.2.1 Synthetic Cathinones ................................................................................................. 5 1.2.1.1 Definition of ‘Synthetic Cathinone’........................................................................ 5 1.2.1.2 History and Current Trends ................................................................................... 6 1.2.1.3 Australian Legislation regarding Synthetic Cathinones .......................................... 9 1.2.1.4 Synthesis of Synthetic Cathinones ....................................................................... 10 1.2.1.5 Profiling of Synthetic Cathinones ........................................................................ 12 1.3 Methylamphetamine ....................................................................................................... 13 1.3.1 Synthesis of Methylamphetamine ........................................................................... 14 1.4 Ephedrine ........................................................................................................................ 16 1.4.1 History and Current Trends ..................................................................................... 16 1.4.2 Legal Status of Ephedrine ........................................................................................ 16 1.4.3 Synthesis of Ephedrine ............................................................................................ 17 1.4.3.1 Synthesis of N-methylalanine .............................................................................. 20 1.5 Profiling of Illicit Substances ............................................................................................ 21 1.5.1 Isotope Ratio Mass Spectrometry (IRMS) ................................................................ 22 1.5.1.1 Natural Abundance of Stable Isotopes ................................................................ 23 1.5.1.2 Reference Standards ........................................................................................... 23 1.5.1.4 Isotopic Fractionation ......................................................................................... 24 1.5.1.5 Instrumentation .................................................................................................. 25 1.5.2 Forensic Applications of IRMS ................................................................................. 26 1.5.2.1 Drug Analysis using IRMS .................................................................................... 28 1.5.2.2 Analysis of Ephedrine, Pseudoephedrine and methylamphetamine using IRMS 29 1.6 Aims and Objectives ........................................................................................................ 32 1.6.1 Isotopic profiling of Synthetic Cathinones ............................................................... 32 iv The Application of Stable Isotope Ratio Mass Spectrometry to Illicit Drug Profiling 1.6.2 Isotopic profiling of Ephedrine synthesised from N-methylalanine ........................ 32 1.7 References ....................................................................................................................... 34 Chapter 2: Methods and Materials 2.1 Materials ......................................................................................................................... 44 i) Solvents, Reagents and Precursors .................................................................................. 44 ii) Standards ........................................................................................................................ 45 2.2 Synthesis.......................................................................................................................... 46 2.2.1 Synthesis of Synthetic Cathinones ........................................................................... 46 2.2.1.1 Synthesis of precursor material1,2........................................................................ 46 2.2.1.2 Synthesis of synthetic cathinones2,3 .................................................................... 47 2.2.1.3 Preparation of synthetic cathinone hydrochloride salts ...................................... 47 2.2.2 Synthesis of Ephedrine ............................................................................................ 47 2.2.2.1 Synthesis of Precursor material ........................................................................... 47 2.2.2.2 Synthesis of Ephedrine6 ....................................................................................... 49 2.3 Profiling of Synthetic Cathinones and Ephedrine samples .................................................... 49 2.3.1 Quantification using Gas Chromatography-Flame Ionisation Spectroscopy (GC-FID) .... 49 2.3.1.1 Sample Preparation ............................................................................................. 49 2.3.1.3 Quantification by GC-FID ..................................................................................... 50 2.3.2 Identification of Synthetic Cathinones and Ephedrine by GC-MS................................... 50 2.3.2.1 Sample Preparation ............................................................................................. 50 2.3.2.2 Identification using GC-MS .................................................................................. 51 2.3.3 Chiral analysis of Ephedrine by CE ........................................................................... 51 2.3.3.1 Preparation of reagents for analysis .................................................................... 51 2.3.3.2 Sample preparation ............................................................................................. 52 2.3.3.3 Chirality determination by CE .............................................................................
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