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Characterization of Synthetic Phenethylamines Using Low- Resolution and High-Resolution Mass Spectrometry

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Characterization of Synthetic Phenethylamines Using Low- Resolution and High-Resolution Mass Spectrometry CHARACTERIZATION OF SYNTHETIC PHENETHYLAMINES USING LOW- RESOLUTION AND HIGH-RESOLUTION MASS SPECTROMETRY By Alexandria Lynn Anstett A THESIS Submitted to Michigan State University in partial fulfillment of the requirements for the degree of Forensic Science – Master of Science 2017 ABSTRACT CHARACTERIZATION OF SYNTHETIC PHENETHYLAMINES USING LOW- RESOLUTION AND HIGH-RESOLUTION MASS SPECTROMETRY By Alexandria Lynn Anstett Definitive identification and differentiation of synthetic designer drugs can be challenging for forensic analysts due to the high structural similarities. The focus in this work was the characterization of synthetic phenethylamines, a common class of designer drugs, using mass spectrometry methods. A set of phenethylamine reference standards was analyzed using both low-resolution and high-resolution mass spectrometry and the mass spectra were probed to identify characteristic and distinguishing features. These features were integrated into a flow- chart style characterization scheme for both low-resolution and high-resolution mass spectra. The characterization scheme for low-resolution data utilizes retention index and neutral losses to indicate phenethylamine structural subclass. Further, isotope patterns and characteristic mass spectral features give a preliminary indication of the identity of substituent. This scheme is immediately implementable into forensic practice because it exploits the instrumentation already used for the identification of controlled substances. The high-resolution version of the characterization scheme offers more robust characterization. From high-resolution mass analysis, exact mass and mass accuracy of each ion were determined and mass defect filters were developed. These mass defect filters were successful in characterizing compounds according to structural subclass. Overall, this research provides tools for the characterization of synthetic phenethylamines and highlights the potential for high-resolution mass spectrometry for forensic applications, should this instrumentation become available in forensic laboratories. ACKNOWLEDGMENTS Foremost, I would like to express my deepest appreciation, gratitude, and thanks to my advisor, Dr. Ruth Smith for her guidance and willingness to share her knowledge, expertise, excitement, and laughter throughout my graduate career at Michigan State University. I thank her for challenging me to grow as a scientist and as a person. My gratitude knowns no bounds and without her, this would not be possible. I would also like to thank my committee member Dr. Victoria McGuffin, for her advice throughout this research and for always offering a different perspective and asking questions that have challenged me and helped me to think critically. I would also like to thank Dr. Steve Dow for serving on my committee on shorter notice and agreeing to read my thesis over the Christmas holiday. Further, I would like to thank those who helped facilitate this research, especially Scott Smith and the staff of the MSU Mass Spectrometry and Metabolomics Core Facility, and David Alonso and Joe Binkley from LECO Corp. for help with instrumentation and data collection. I am also grateful to the National Institute of Justice who supported this research via grant number 2015-IJ-CX-K008. Points of view in this thesis are those of the author and do not necessarily represent the official position or policies of the U.S. Department of Justice. Additionally, I would like to thank current and past members of the Forensic Chemistry group for their encouragement, guidance, patience, and support- especially sitting through countless hours of AAFS and thesis defense practices. A special thank you to Fanny Chu, Natasha Eklund, Cindy Kaeser, Amanda Setser, Barb Fallon, and Kristen Reese. An extra special thank you to Trevor Curtis for being my “partner in crime” and making sure I always had a friend to eat with. I would also like to thank my dearest friend and roommate Brianna Bermudez iii for taking Moose and I in, and always offering encouragement, advice, laughs, food, and love. Further, to my “favorite” biologist, I would like to thank Alyssa Badgley for being there for me as a best friend and shoulder to lean on throughout my entire graduate school journey. I honestly couldn’t have done it without you, and wouldn’t have wanted too anyway. Thanks for being the best “trace” partner, tailgater, and overall Spartan enthusiast I could have ever asked for (“GREEEN”). Finally, I would like to thank my friends and family, especially my “moms” for their support from across the country, Tristan Musser for his endless love, support, and patience and my parents, Monica and Paul, for their unwavering, unconditional, encouragement and love in everything I’ve ever done. This one’s for you guys. I am truly grateful to you all and couldn’t have made it this far without you. iv TABLE OF CONTENTS LIST OF TABLES ........................................................................................................................ vii LIST OF FIGURES ..................................................................................................................... viii I. Introduction ................................................................................................................................. 1 1.1 Synthetic Designer Drugs...................................................................................................... 1 1.2 Current Methods of Analysis of Submitted Drug Samples and Limitations ........................ 3 1.3 Current Research of Synthetic Designer Drugs .................................................................... 4 1.4 Research Objectives and Goals ............................................................................................. 8 REFERENCES ............................................................................................................................. 12 II. Theory ...................................................................................................................................... 15 2.1 Chromatography Overview ................................................................................................. 15 2.2 Gas Chromatography Overview .......................................................................................... 15 2.2.1 Retention Index............................................................................................................. 19 2.3 Mass Spectrometry Overview ............................................................................................. 20 2.3.1 Mass Analysis: Single Quadrupole Mass Analyzer ..................................................... 21 2.3.2 Mass Analysis: Time-of-Flight Mass Analyzer............................................................ 24 2.3.3 Comparison of Low-Resolution and High-Resolution Mass Spectra .......................... 26 2.4 Mass Defect ......................................................................................................................... 28 2.4.1 Kendrick Mass Defect .................................................................................................. 29 REFERENCES ............................................................................................................................. 30 III. Materials and Methods ............................................................................................................ 32 3.1 Reference Standards ............................................................................................................ 32 3.2 Gas Chromatography-Mass Spectrometry (GC-MS) Analysis ........................................... 35 3.3 Data Processing ................................................................................................................... 37 3.4 Mass Defect Filters.............................................................................................................. 38 3.4.1 Absolute Mass Defect Filters ....................................................................................... 38 3.4.2 Kendrick Mass Defect Filters ....................................................................................... 39 APPENDIX ................................................................................................................................... 41 IV. Characterization of Synthetic Phenethylamines by Low-Resolution Mass Spectrometry ..... 43 4.1 Retention Index ................................................................................................................... 43 4.2 Electron Ionization Mass Spectra of Synthetic Phenethylamine Subclasses ...................... 45 4.3 Neutral Losses from Molecular Ion to Distinguish 2C- from NBOMe-Phenethylamines .. 49 4.4 Distinction and Identification of Common Substituents for 2C- and NBOMe- Phenethylamines........................................................................................................................ 53 4.4.1 Halogen Substitutions ................................................................................................... 53 4.4.2 Sulfur and Nitro Substitutions ...................................................................................... 59 4.5 Scheme for Characterization of Synthetic Phenethylamines using Low-Resolution Mass Spectra ....................................................................................................................................... 62 4.6 Summary ............................................................................................................................
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