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Detection and Characterization of Pyromarkers of Smoked Drugs of Abuse Graduate Theses, Dissertations, and Problem Reports 2012 Detection and characterization of pyromarkers of smoked drugs of abuse Rona Kiyomi Nishikawa West Virginia University Follow this and additional works at: https://researchrepository.wvu.edu/etd Recommended Citation Nishikawa, Rona Kiyomi, "Detection and characterization of pyromarkers of smoked drugs of abuse" (2012). Graduate Theses, Dissertations, and Problem Reports. 4904. https://researchrepository.wvu.edu/etd/4904 This Dissertation is protected by copyright and/or related rights. It has been brought to you by the The Research Repository @ WVU with permission from the rights-holder(s). You are free to use this Dissertation in any way that is permitted by the copyright and related rights legislation that applies to your use. For other uses you must obtain permission from the rights-holder(s) directly, unless additional rights are indicated by a Creative Commons license in the record and/ or on the work itself. This Dissertation has been accepted for inclusion in WVU Graduate Theses, Dissertations, and Problem Reports collection by an authorized administrator of The Research Repository @ WVU. For more information, please contact [email protected]. DETECTION AND CHARACTERIZATION OF PYROMARKERS OF SMOKED DRUGS OF ABUSE Rona Kiyomi Nishikawa Dissertation submitted to the Eberly College of Arts and Sciences at West Virginia University in partial fulfillment of the requirements for the degree of Doctor of Philosophy in Chemistry Committee of Advisors: Suzanne C. Bell, Ph.D., Chair R. Lloyd Carroll, Ph.D. Patrick S. Callery, Ph.D. Harry O. Finklea, Ph.D. Keith B. Morris, Ph.D. C. Eugene Bennett Department of Chemistry Morgantown, West Virginia 2012 Keywords: Fentanyl, Heroin, Pyrolysis, Pyromarkers, GC/MS Copyright © 2012 Rona Kiyomi Nishikawa 1 Abstract DETECTION AND CHARACTERIZATION OF PYROMARKERS OF SMOKED DRUGS OF ABUSE Rona Kiyomi Nishikawa Smoking or inhalation has increased in popularity as the choice route of administration of drugs of abuse amongst drug abusers. Combustion products associated with the smoking event (pyromarkers) of these smoked drugs of abuse can be useful in post mortem toxicological analysis both for investigative and public health applications. A method using analytical pyrolysis was developed to simulate the smoking process used for illicit drugs, which is significantly different than methods used for studies of conventional tobacco smoking, This method was used to identify possible markers associated smoked fentanyl and mixes of heroin and fentanyl. Thermocouple temperature probes were used to analyze the temperatures obtained through smoking the fentanyl transdermal patches (FTPs) in means of the “chasing the dragon” technique. These temperatures were then applied to the pyrolysis gas chromatography (Py-GC/MS) to mimic these smoking conditions to determine pyromarkers that were produced. The presence of a trap on the pyrolysis unit allowed for aerobic conditions by exposing the pyromarkers to air. A second advantage of trapping is preconcentration of pyromarkers. The method enhanced the recovery and afforded a positive identification of the pyromarkers. The methods and models developed here can be extended to any smoked drug, including drugs of current concern such as cannabinomimetics and incense/bath salt compositions. Dedication This dissertation is dedicated to my parents, grandparents, sister, brother-in-law, niece, Uncle Jim, Aunty June, Aunty Georgia, cousins Kyle and Blaine, and Thomas. It was their endless love, support, encouragement, and endless boxes of care packages have undoubtedly provided me the foundation and motivation for me to succeed. ii Acknowledgments First and foremost, I would like to acknowledge Dr. Suzanne Bell, for her help, advice, mentorship, support, and friendship throughout my graduate study. My exploration of smoked drugs of abuse would not have been possible without the help of Dr. Patrick Callery and Dr. James Kraner who never hesitated to share their advice, suggestions, and ideas. I am most grateful to Dr. R Lloyd Carroll for his enthusiasm in chemistry, advice, and endless support from my very start at WVU. Technical assistance of Allen Burns and Phillip Tucker is also greatly appreciated. I would like to thank my committee members for their time and patience in reviewing this research. Their helpful suggestions and valuable discussions are greatly acknowledged. I would like to thank Jennifer Mercer and Melissa Gayton Ely and the other current and past members of the Bell Group whom I have had pleasure to work with. Lastly, I firmly believe that I would not have survived graduate school if it had not been for my research group members Holly McCall, Jordan Moran, and Xinya Zhang. The true genuine friendships shared between us have undoubtedly made this journey not only successful, but also sore to my stomach with humor and laughter. We learned, guided, and took care of one another like a family. Each has made huge impact on my life and the memories shared between us will never be forgotten and will continue to flourish into the future. iii Table of Contents Abstract ..................................................................................................................................... i Dedication ................................................................................................................................ ii Acknowledgments .................................................................................................................. iii Table of Contents ................................................................................................................... iv List of Tables ......................................................................................................................... vii List of Figures ....................................................................................................................... viii List of Abbreviations, Symbols/Nomenclature..................................................................... x Chapter 1: Introduction ......................................................................................................... 1 1.1.0 Development of Research ............................................................................................ 2 1.2.0 Compounds of Interest ................................................................................................. 9 1.2.1 Fentanyl.................................................................................................................. 13 1.2.2 Heroin .................................................................................................................... 18 1.2.3 Smoking Opioids by “Chasing the Dragon” .......................................................... 24 1.3.0 Methods of Degradation ............................................................................................ 25 1.4.0 Instrumentation .......................................................................................................... 33 1.4.1 Thermocouple ........................................................................................................ 33 1.4.2 Py-GC/MS.............................................................................................................. 36 Chapter 2: Application of the Py-GC/MS to Mimic the Smoking Conditions of Fentanyl and FTPs ................................................................................................................................ 44 2.1.0 Introduction ................................................................................................................ 45 2.2.0 Materials and Methods ............................................................................................... 47 2.2.1 Py-GC/MS.............................................................................................................. 47 2.3.0 Results and Discussion .............................................................................................. 51 2.3.1 Pyrolytic Degradation Pathways of Pyromarkers .................................................. 54 2.3.2 Comparison of Fentanyl HCl and FTPs Under Anaerobic and Aerobic Conditions ......................................................................................................................................... 59 2.4.0 Conclusions ................................................................................................................ 64 iv Chapter 3: Determination of the Temperature Characteristics of Smoking FTPs Using the “Smoking the Dragon” Method..................................................................................... 65 3.1.0 Introduction ................................................................................................................ 66 3.2.0 Materials and Methods ............................................................................................... 68 3.2.1 Thermocouple ........................................................................................................ 68 3.2.2 Setup Diagram ....................................................................................................... 68 3.3.0 Results and Discussion .............................................................................................. 75 3.4.0 Conclusions ................................................................................................................ 79
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