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A Review of the Collision Induced Dissociation Fragmentation and the Metabolism of Synthetic Cathinone Derivatives

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A Review of the Collision Induced Dissociation Fragmentation and the Metabolism of Synthetic Cathinone Derivatives A review of the collision induced dissociation fragmentation and the metabolism of synthetic cathinone derivatives Nichola Cunningham A thesis submitted in fulfilment of the requirements for the degree of Master of Forensic Science (Professional Practice) In The school of Veterinary and Life Sciences Murdoch University Supervisors: Dr John Coumbaros Associate Professor James Speers Semester 1 2018 i Declaration I declare that this thesis does not contain any material submitted previously for the award of any other degree or diploma at any university or other tertiary institution. Furthermore, to the best of my knowledge, it does not contain any material previously published or written by another individual, except where due reference has been made in the text. Finally, I declare that all reported experimentations performed in this research were carried out by myself, except that any contributions by others, with whom I have worked is explicitly acknowledged. Signed: Nichola Cunningham ii Acknowledgments Firstly, I would like to thank my supervisor John Coumbaros for all of your support, feedback, and advice throughout this project. You have been an invaluable help and I am grateful for all the time you invested in my work. To Bob Mead, thank you so much for all your help with this project. You have always been a support throughout the years and this was no exception; thank you for the time and feedback you provided me along the way. Finally, to my family and friends who have supported me through this, and the entire degree, thank you! I finally made it through! iii Table of Contents Title page ....................................................................................................................................... i Declaration .................................................................................................................................... ii Acknowledgments ......................................................................................................................... iii PART ONE Literature Review ........................................................................................................................... 1– 42 PART TWO Manuscript ................................................................................................................................... 43 – 66 iv PART ONE: Literature Review A review of the metabolism and mass spectral fragmentation of synthetic cathinones 1 Abstract Synthetic cathinones constitute one of the most commonly abused new psychoactive substances. The rapid development of synthetic cathinones creates a challenge for forensic laboratories to develop and maintain analytical methods for identifying and quantifying synthetic cathinones and their metabolites in illicit drug and toxicological samples. The characterisation of synthetic cathinone metabolites is therefore important for both developing an understanding of their pharmacokinetics and for identifying unique metabolites that could be used for identification. In this review, the current state of knowledge regarding the metabolism of synthetic cathinones will be discussed; focussing primarily on the human in vitro and in vivo metabolism, with the objective of providing a systematic overview of the currently known metabolic profiles. In addition to this, the mass-spectral dissociation fragmentation pathways of synthetic cathinones will be reviewed in an attempt to identify common fragmentation patterns that may assist in the identification of previously unidentified synthetic cathinones. Keywords: Synthetic cathinones; Metabolism; Cathinone Fragmentation patterns; Novel psychoactive substances; Collision induced dissociation. 2 Table of Contents Abstract ................................................................................................................................................ 2 List of Figures ........................................................................................................................................ 4 List of Tables ......................................................................................................................................... 4 Abbreviations ........................................................................................................................................ 5 CHAPTER ONE: Introduction ................................................................................................................. 6 1.1 Cathinone pharmacology and mechanism of action ................................................................... 8 1.2 Chemical structure and classification of cathinone derivatives .................................................. 9 1.2.2 Methylenedioxy-N-alkylated derivatives............................................................................ 11 1.2.3 N-pyrrolidine substituted cathinone derivatives ................................................................ 11 1.2.4 Methylenedioxy-N-pyrrolidine cathinone derivatives ........................................................ 14 1.3 Analytical methods for the identification of cathinone derivatives .......................................... 14 1.4 Methods for metabolic profiling ............................................................................................... 16 1.5 Overview of phase I and phase II metabolism........................................................................... 17 2.1 Metabolism of N-alkylated cathinone derivatives .................................................................... 20 2.2 Metabolism of 3,4-methylenedioxy cathinone derivatives ....................................................... 22 2.3 Metabolism of N-Pyrrolidine cathinone derivatives.................................................................. 24 2.4 Metabolism of 3,4-methylenedioxy-N-alkylated cathinone derivatives ................................... 27 2.5 Summary of synthetic cathinone metabolism ........................................................................... 28 CHAPTER THREE: Cathinone fragmentation patterns ......................................................................... 29 3.1 General fragmentation patterns of synthetic cathinones ......................................................... 29 3.2 Fragmentation patterns for N-pyrrolidinyl substituted cathinone derivatives.......................... 34 3.3 Summary of fragmentation ....................................................................................................... 35 CHAPTER FOUR: Conclusion ................................................................................................................ 36 REFERENCES ........................................................................................................................................ 37 3 List of Figures Page Figure 1: Comparison of the natural cathinone structure (left) and the amphetamine structure (right) ................................................................................................................... 8 Figure 2: The generic structure of cathinone derivatives. ................................................................... 9 Figure 3: The chemical structure of some common N-alkylated cathinone derivatives. .......................................................................................................................... 10 Figure 4: Chemical structure of 3,4-methylenedioxy-N-alkylated cathinone derivatives (A) and the structurally related MDAs (B) ............................................................................. 11 Figure 5: Chemical structures of the N-pyrrolidine cathinone derivatives and 3,4-methylenedioxy-N-pyrrolidine cathinone derivatives ................................................... 13 Figure 6: A schematic of the major pathways of drug biotransformation .......................................... 18 Figure 7: Schematic representation of phase I cathinone metabolism. .............................................. 19 Figure 8: The proposed metabolic pathway of mephedrone in humans ............................................ 21 Figure 9: Proposed in vitro and in vivo metabolic pathway for methylone in humans. ...................... 23 Figure 10: Proposed metabolic pathway for α-PVP based on metabolites observed in human urine and HLM ..................................................................................................................... 25 Figure 11: A proposed metabolic pathway for PV9 in humans. .......................................................... 26 Figure 12: The proposed metabolic pathway for MDPV in humans. ................................................... 28 Figure 13: A schematic representation of the postulated general CID fragmentation postulated of synthetic cathinones. ...................................................................................................... 32 Figure 14: A postulated fragmentation pattern of 3,4-methylenedioxy substituted cathinone derivatives ........................................................................................................................... 33 Figure 15: The proposed generalised fragmentation pathways for pyrrolidinyl substituted cathinone derivatives. ........................................................................................................ 35 List of Tables Table 1: Summary of the names, formulae and structures of the 39 investigated cathinone derivatives .............................................................................................................................
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