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Mass Spectral, Infrared and Chromatographic Studies on Designer Drugs of the Piperazine Class by Karim M. Hafiz Abdel-Hay a Diss

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Mass Spectral, Infrared and Chromatographic Studies on Designer Drugs of the Piperazine Class by Karim M. Hafiz Abdel-Hay a Diss Mass Spectral, Infrared and Chromatographic Studies on Designer Drugs of the Piperazine Class by Karim M. Hafiz Abdel-Hay A dissertation submitted to the Graduate Faculty of Auburn University in partial fulfillment of the requirements for the degree of Doctor of Philosophy Auburn, Alabama May 7, 2012 Approved by C. Randall Clark, Chair, Professor of Pharmacal Sciences Jack DeRuiter, Professor of Pharmacal Sciences Forrest Smith, Associate Professor of Pharmacal Sciences Angela Calderon, Assistant Professor of Pharmacal Sciences Abstract The controlled drug 3,4-methylenedioxybenzylpiperazine (3,4-MDBP) has regioisomeric and isobaric substances of mass equivalence, which have similar analytical properties and thus the potential for misidentification. The direct regioisomers of 3,4-MDBP include the 2,3- methylenedioxy substitution pattern and the indirect regioisomers include the three ring substituted methoxybenzoylpiperazines. The ethoxy and methoxymethyl ring substituted benzylpiperazines constitute the major category of isobaric substances evaluated in this study. The direct and indirect regioisomers of 3,4-MDBP and also isobaric substances related to MDBP were synthesized and compared to 3,4-MDBP by using gas chromatographic and spectrophotometric techniques. The GC-MS studies of the direct regioisomers and isobaric substances of 3,4-MDBP indicated that they can not be easily differentiated by mass spectrometry. The synthesized compounds were converted to their perfluoroacyl derivatives, trifluoroacetyl (TFA), pentafluoropropionyl amides (PFPA) and heptafluorobutryl amides (HFBA), in an effort to individualize their mass spectra and to improve chromatographic resolution. Derivatized 3,4-MDBP was not distingushed from its derivatized regioisomers or isobars using mass spectrometry. No unique fragment ions were observed for the various regioisomeric and the isobaric compounds. Gas chromatographic studies indicated that the optimum separation of regioisomers and isobaric compounds of 3,4-MDBP was obtained when a 100% trifluoropropyl methyl polysiloxane column was used at gradient temperature program ii rates. Exact mass determination techniques such as gas chromatography coupled to time of fight mass spectrometric detection (GC-TOF-MS) was used and proved to be successful in discriminating among isobaric compounds that have the same nominal mass but are different in their elemental composition and hence their exact masses. On the other hand, GC-TOF-MS is not a successful tool to differentiate between regioisomers that have both the same nominal and exact masses. In addition, the gas chromatography coupled to infrared detection (GC-IRD) proved to be an excellent tool in differentiating 3,4-MDBP from all of its regioisomers and isobars. Other ring substituted benzylpiperazines such as chloro, methoxy and methylbenzylpiperazines were prepared and their analytical properties were studied in this dissertation. Other chemical classes of piperazines were also synthesized and evaluated during this study. Some ring substituted benzoylpiperazines, 1-(phenyl)-2-piperazinopropanes (PPPs) that have amphetamine-like side chain and 1-(phenyl)-2-piperazinopropanones which have cathinone-like side chain (PPPOs) were synthesized in the lab. Their mass spectral, infrared and gas chromatographic separation and properties were studied too. In addition to that, isotope labeling experiments such as deuterium (D) and carbon 13 (13C) labeling were used to confirm mass spectrometric fragmentation mechanisms that result in the formation of some key fragment ions or to confirm the elemental composition of these fragment ions. iii Acknowledgments In the name of Allah, the Most Beneficent, the Most Merciful I begin. First and foremost I want to say ―Alhamdolellah‖ thanks god for your help and giving me the power to achieve this humble piece of work. During the preparation of this dissertation many people, both in USA and Egypt have given me support. I am so grateful to them all. Especially I would like to thank: Professor C. Randall Clark, no words can express my sincere gratitude to him, for his continuous encouragement, guidance, support and patience. His lessons in the art of chromatography and mass spectrometry are invaluable to me. With such a wonderful personality, he makes you feel that the advisor-graduate student relationship is a father- son relationship which I will be proud of for the rest of my life. Professor Jack DeRuiter, who significantly helped developing my synthesis skills through lectures and support in the laboratory. His encouragement was of utmost importance. Dr. Forrest Smith, his outstanding lectures in organic synthesis enabled me to have a solid background that should enable me to sucessfuly continue my career in medicinal chemistry. Dr. Angela Calderon‘s lectures in the LC-MS and exact mass determination were so helpful for me throughout my research work. In addition to all these people, I would like to thank Dr. Tamer Awad for his sincere help inside and outside the lab. I would also like to express my thanks to my family in Egypt for their love and support and to my sincere gratefulness to my beloved wife, Rasha, for her patience, encouragement and the motive to finish this work. iv Table of Contents Abstract ........................................................................................................................................... ii Acknowledgments.......................................................................................................................... iv List of Tables .................................................................................................................................. x List of Figures ................................................................................................................................ xi List of Schemes ............................................................................................................................. xv List of Abbreviations .................................................................................................................. xvii 1. Literature Review.................................................................................................................... 1 1.1. Introduction ..................................................................................................................... 1 1.2. History............................................................................................................................. 4 1.3. Pharmacology ................................................................................................................. 7 1.3.1. Pharmacodynamics ................................................................................................... 7 1.3.2. Subjective effects ...................................................................................................... 7 1.3.3. Toxic effects............................................................................................................ 10 1.3.4. Christchurch study .................................................................................................. 10 1.4. Metabolism ................................................................................................................... 11 1.4.1. Metabolism of BZP ..................................................................................................... 12 1.4.2. Metabolism of 3,4-MDBP ...................................................................................... 13 1.4.3. Metabolism of TFMPP ........................................................................................... 14 1.4.4. Metabolism of mCPP .............................................................................................. 15 1.4.5. Metabolism of p-(OMePP) ..................................................................................... 16 1.5. Analytical methods used to separate and identify piperazines ..................................... 17 1.5.1. Gas chromatography-mass spectrometry (GC-MS) ................................................ 17 1.5.2. Gas chromatography with infrared detection (GC-IRD) ........................................ 18 1.5.3. Nuclear magnetic resonance (NMR) ...................................................................... 19 1.5.4. Liquid chromatography- electrospray ionization mass spectrometric detection (LC- MS) and liquid chromatography- ultraviolet detection (HPLC-UV) .................................... 20 1.6. Project rational ................................................................................................................... 20 1.7. Statement of research objectives .................................................................................. 22 2. Synthesis of the Regioisomeric and Isobaric Piperazines......................................................... 26 v 2.1. Synthesis of the ring substituted benzylpiperazines .......................................................... 27 2.1.1. Synthesis of the methylenedioxybenzylpiperazines (MDBPs) ................................... 28 2.1.2. Synthesis of the methoxymethylbenzylpiperazines (MMBPs) ................................... 29 2.1.2.1. Synthesis of 2-methoxy-6-methylbenzaldehyde .................................................. 31 2.1.2.2. Synthesis of 3-methoxy-4-methylbenzaldehyde .................................................. 31 2.1.2.3. Synthesis of 2-methoxy-3-methylbenzaldehyde, 2-methoxy-4-
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