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Florida International University FIU Digital Commons FIU Electronic Theses and Dissertations University Graduate School 9-17-2015 Comprehensive Analysis of Emerging New Psychoactive Substances by Ion Mobility Spectrometry and Mass Spectrometry Seongshin Gwak Florida International University, [email protected] DOI: 10.25148/etd.FIDC000157 Follow this and additional works at: https://digitalcommons.fiu.edu/etd Part of the Analytical Chemistry Commons Recommended Citation Gwak, Seongshin, "Comprehensive Analysis of Emerging New Psychoactive Substances by Ion Mobility Spectrometry and Mass Spectrometry" (2015). FIU Electronic Theses and Dissertations. 2291. https://digitalcommons.fiu.edu/etd/2291 This work is brought to you for free and open access by the University Graduate School at FIU Digital Commons. It has been accepted for inclusion in FIU Electronic Theses and Dissertations by an authorized administrator of FIU Digital Commons. For more information, please contact [email protected]. FLORIDA INTERNATIONAL UNIVERSITY Miami, Florida COMPREHENSIVE ANALYSIS OF EMERGING NEW PSYCHOACTIVE SUBSTANCES BY ION MOBILITY SPECTROMETRY AND MASS SPECTROMETRY A dissertation submitted in partial fulfillment of the requirements for the degree of DOCTOR OF PHILOSOPHY in CHEMISTRY by Seongshin Gwak 2015 To: Dean Michael R. Heithaus College of Arts and Sciences This dissertation, written by Seongshin Gwak, and entitled Comprehensive Analysis of Emerging New Psychoactive Substances by Ion Mobility Spectrometry and Mass Spectrometry, having been approved in respect to style and intellectual content, is referred to you for judgment. We have read this dissertation and recommend that it be approved. _______________________________________ Anthony P. DeCaprio _______________________________________ Fenfei Leng _______________________________________ Wenzhi Li _______________________________________ Bruce R. McCord ______________________________________ José R. Almirall, Major Professor Date of Defense: September 17, 2015 The dissertation of Seongshin Gwak is approved. _______________________________________ Dean Michael R. Heithaus College of Arts and Sciences _______________________________________ Dean Lakshmi N. Reddi University Graduate School Florida International University, 2015 ii © Copyright 2015 by Seongshin Gwak All rights reserved. iii DEDICATION I would like to dedicate this dissertation to my family and my fiancée for their endless love, support, and encouragement. iv ACKNOWLEDGMENTS First of all, I would like to express my deepest gratitude to Dr. José Almirall, my advisor, for his support and guidance. He motivated me all the time of research during my doctoral career. I also would like to thank my dissertation committee, Dr. Anthony DeCaprio, Dr. Fenfei Leng, Dr. Wenzhi Li, and Dr. Bruce McCord, for their support and guidance, especially for taking time out of their busy schedules. I would like to acknowledge the National Institute of Justice for the research grant (Award No. 2011-DN-BX-K531) and the University Graduate School of Florida International University for the Dissertation Year Fellowship. This research would not have been possible without their financial support. Thanks to the Senate Graduate and Professional Student Committee and the College of Arts and Sciences of Florida International University for travel funding to attend a number of scientific conferences throughout my doctoral study. I would like to thank Dr. Luis Arroyo-Mora from the Forensic & Analytical Toxicology Facility at Florida International University for his technical support and the use of the Agilent 6530 Q-TOF mass analyzer. I also appreciate Oliver Spicer, Jr. from the Analytical Section at Miami-Dade Police Department Forensic Services Bureau for providing the seized drug samples. Many thanks to my fellow colleagues and friends whom I have met during my doctoral degree for their encouragement and support. I greatly appreciate all formal and present A-Team members for their help and sharing all the fun inside and outside of the laboratory. Thanks to all my friends outside of the laboratory for sharing all good memories during this long journey. v Most importantly, I would like to thank my family in Korea for their spiritual support during my study abroad as well as through my entire life. Special thanks to my fiancée for her support, patience, and love. I am very grateful to have all of them in my life. vi ABSTRACT OF THE DISSERTATION COMPREHENSIVE ANALYSIS OF EMERIGING NEW PSYCHOACTIVE SUBSTANCES BY ION MOBILITY SPECTROMETRY AND MASS SPECTROMETRY by Seongshin Gwak Florida International University, 2015 Miami, Florida Professor José R. Almirall, Major Professor In the new era of drug abuse, the proliferation of new psychoactive substances (NPS), commonly referred to as designer drugs or legal highs, has been a global concern. These substances are produced to circumvent current legislation for controlled substances with minor modifications in their chemical structure. Although many efforts have been made previously, the characterization of such substances are still challenging because of (1) the continual emergence of newly identified substances, (2) the lack of a universal screening test for NPS that are structurally similar to each other, and (3) the complex and time-consuming chromatographic techniques currently used. Therefore, it is necessary to develop novel analytical methods that can be readily adapted by forensic laboratories to overcome these challenges. In this dissertation, various analytical techniques have been evaluated for qualitative analysis of these emerging NPS. For rapid screening purposes, a commercial ion vii mobility spectrometry with a 63Ni ion source (63Ni-IMS) and also direct analysis in real time coupled to a quadrupole time-of-flight mass spectrometer (DART-QTOF-MS) were investigated first. The results showed that rapid detection by 63Ni-IMS and identification by DART-QTOF-MS can be achieved with sub-nanogram detection capability and high speed total analysis time less than two minutes. In recent developments of gas chromatography mass spectrometry (GC-MS), gas chromatography (GC) has been coupled to state-of-the-art mass spectrometers, including triple quadrupole (MS/MS) and quadrupole time-of-flight (QTOF). It was revealed that the application of GC-MS/MS and GC-QTOF facilitates the unambiguous identification of emerging NPS with a chemical ionization (CI) source. In addition, constitutional isomers of NPS were differentiated with the capabilities of product ion scan and multiple reaction monitoring (MRM) modes. Finally, the coupling of IMS with a mass spectrometer (IMS-MS) was investigated as an alternative confirmatory technique. With the development of an optimal solvent system in the electrospray ionization (ESI) process, the rapid analysis and identification of synthetic cathinone was successfully achieved less than five minutes. As a proof-of-concept, seized drugs samples provided by a local forensic laboratory were analyzed using these developed methods by various analytical techniques. The results from these seized samples are also presented in this evaluation. viii TABLE OF CONTENTS CHAPTER PAGE CHAPTER 1. INTRODUCTION ....................................................................................... 1 1.1 Research Motivation ............................................................................................ 2 1.2 Research Hypothesis ............................................................................................ 4 1.3 Significance of Research ...................................................................................... 5 CHAPTER 2. BACKGROUND ......................................................................................... 7 2.1 Introduction to NPS .............................................................................................. 7 2.1.1 Synthetic Cannabinoids ................................................................................ 7 2.1.2 Synthetic Cathinones .................................................................................... 8 2.1.3 Phenethylamines ......................................................................................... 10 2.1.4 Ketamine and Phencyclidine-type Substances ............................................ 11 2.1.5 Tryptamines ................................................................................................ 12 2.1.6 Piperazines .................................................................................................. 13 2.2 Forensic Analysis of Controlled Substances ...................................................... 15 2.3 Principles of Instrumentation ............................................................................. 16 2.3.1 Gas Chromatography .................................................................................. 16 2.3.2 Ion Mobility Spectrometry .......................................................................... 18 2.3.2.1 Radioactive 63Ni ionization source ...................................................... 22 2.3.2.2 Coupling of Electrospray Ionization and Mass Spectrometry with Ion Mobility Spectrometry ......................................................................... 23 2.3.3 Mass Spectrometry ...................................................................................... 25 2.3.3.1 Ion Sources .......................................................................................... 26 2.3.3.2 Mass Analyzers...................................................................................
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