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Downloaded From: Usage Rights: Creative Commons: Attribution-Noncommercial-No Deriva- Tive Works 4.0 Zuway, Khaled Youssff (2018) Development of new methods of detection and quantification of controlled and new psychoactive substances (NPS) us- ing liquid chromatography-amperometric detection (LC-AD). Doctoral thesis (PhD), Manchester Metropolitan University. Downloaded from: https://e-space.mmu.ac.uk/622108/ Usage rights: Creative Commons: Attribution-Noncommercial-No Deriva- tive Works 4.0 Please cite the published version https://e-space.mmu.ac.uk Development of New Methods of Detection and Quantification of Controlled and New Psychoactive Substances (NPS) using Liquid Chromatography- Amperometric Detection (LC-AD) A thesis submitted in partial fulfilment of the requirements of the Manchester Metropolitan University for the degree of Doctor of Philosophy. By Khaled Youssff Zuway School of Science and the Environment Faculty of Science and Engineering Manchester Metropolitan University May 2018 Author’s declaration “I declare that none of the work detailed herein has been submitted for any other award at Manchester Metropolitan University or any other Institution.” “I declare that, except where specifically indicated, all the work presented in this report is my own, and I am the sole author of all parts. I understand that any evidence of plagiarism and/or the use of unacknowledged third part data will be dealt with as a very seriousmatter.” Signature Date: 04-February-2018 I “Read! In the name of your Allah, who has created (all that exists).” Al Qur’an Surah Al Alaq ayah 1 “And mankind has not been given of knowledge except a little.” Al Qur’an Surah Al Isra ayah 85 II Abstract The global increase in the prevelance and abuse of new psychoactive substances (NPS) has required the development of new analytical methods for rapid, selective and inexpensive protocols for both their separation and detection. Electrochemical sensing of these compounds has been demonstrated to be an effective method for their in-field detection, either in their pure form or the presence of common adulterants. The electrochemical technique can differentiate between structurally-related phenethylamines (for example (±)-paramethoxyamphetamine and (±)-3,4-methylene dioxymethamphetamine, however it is limited in its ability to distinguish between structurally-related cathinone-derivatives, for example (±)-4- mephedrone and (±)-4-methyl-N-ethycathinone. The HPLC-AD protocol obtained a cost-effective, reproducible, and reliable sensor platform for detection of the target analytes by simultaneous HPLC-UV and amperometric detection protocol. Additionally, the simultaneous HPLC-UV and amperometric detection protocol detailed herein shows a marked improvement in selectively discriminating between structurally related compounds. This thesis demonstrates, for the first time, the combination of HPLC-UV with amperometric detection (HPLC-AD) for the detection and quantitative analysis of new psychoactive substances using a commercially available impinging jet (LC-FC- A system) or using a custom-made iCell channel flow-cell system (LC-FC-B), both incorporating embedded graphite screen-printed macroelectrodes. The method demonstrates the application of a cost-effective, reproducible, and reliable sensor platform for the simultaneous HPLC-UV and amperometric detection of target analytes. III Although the amperometric detection (HPLC-AD) system that has been developed is not as sensitive as standard HPLC-UV detection,both LC-FC-A and LC-FC-B show a good agreement between the quantitative electroanalytical data. Therefore, they are suitable for the detection and quantification of new psychoactive substances, either in their pure form or within complex mixtures. Additionally, the simultaneous HPLC-AD protocol shows a marked improvement and advantage over previously reported electroanalytical methods.The electroanalytical methods were either unable to selectively differentiate between structurally related synthetic cathinones (e.g. (±)-mephedrone and (±)-4-MEC (Smith et al., 2014a), or utilised harmful and restrictive materials in their design by adding the illegal compounds in combination with the legal compounds. IV Table of contents Author’s declaration I Abstract III Table of contents V List of tables XII List of figures XXIV List of equations XXVIII Published work (from this thesis) XXIX Abbreviation and Acronyms XXX Acknowledgments XXXIV 1 Chapter 1: Introduction and literature review 1 1.1 New psychoactive substances. 1 1.2 Emergence/prevalence of NPS 3 1.3 Prevalence of NPSs 4 1.4 Misuse of Drugs Act (1971) 6 1.5 Classification of controlled and new/novel psychoactive substances 11 1.5.1 Phenethylamine (amphetamine, methamphetamine and MDMA) 12 1.5.2 Synthetic cathinones 16 1.5.3 Dissociative anaesthetics (regioisomers of methoxyephenidine and fluoroephenidine) 23 1.6 Analytical techniques for the detection of NPS 26 1.6.1 The principle of chromatography 29 1.6.2 Electrochemistry 32 1.6.3 Application of high performance liquid chromatography- electrochemical detection (HPLC-D) 36 1.7 Study aims and objectives 39 2 Chapter 2: Materials and methods 41 2.1 Chemicals 41 2.1.1 Synthesis of (±)-methoxyephenidine regioisomers 42 V 2.1.2 Synthesis of (±)-fluoroephenidine regioisomers 43 2.2 Instrumental details 43 2.2.1 High performance liquid chromatography (HPLC) 43 2.2.2 Electrochemistry flow cells used in liquid chromatography- amperometric detection (HPLC-AD) 44 2.2.3 Screen-printing electrodes 45 2.2.4 HPLC-AD protocol 45 2.3 Preparation of buffer solutions: 46 2.3.1 Preparation of aqueous-50 mM potassium dihydrogen phosphate (K2H2PO4)-100 mM potassium chloride buffer (pH 3.2). 46 2.3.2 Preparation of aqueous 10 mM ammonium acetate-100 mM potassium chloride buffer (pH 4.3) 47 2.3.3 Preparation of aqueous 10 mM ammonium formate-100 mM potassium chloride buffer (pH 3.5) 47 2.3.4 Preparation of aqueous 20 mM ammonium acetate-100 mM potassium chloride buffer (pH 7) 47 2.4 Preparation of mobile phases 48 2.5 Determination the void time (t0) of HPLC 48 2.6 Detection and quantification of (±)-MDMA in the presence of (±)-MA and (±)-PMA by using high performance liquid chromatography-amperometric detection 49 2.6.1 Preparation of standard solutions fordetermination of λmax of the UV detector 49 2.6.2 Sample preparation for HPLC method development 49 2.6.3 Optimisation of potential for amperometric detection (AD) 49 2.6.4 Optimisation of linear velocity for amperometric detection (AD) 50 2.6.5 Optimisation of HPLC-AD amperometric response under varying pH 50 2.6.6 Calibration standards (pure substances): 51 2.6.7 Specificity standards 51 2.6.8 Accuracy of the study 51 2.6.9 Street samples 52 2.7 Detection and quantification of (±)-mephedrone; (±)-4-MEC and caffeine using high performance liquid chromatography-amperometric detection 52 2.7.1 Preparation of solutions to determination λmax of the UV detector: 52 2.7.2 Sample preparation for HPLC method development 52 VI 2.7.3 Optimisation of potential for amperometric detection (AD) 53 2.7.4 Optimisation of linear velocity for amperometric detection (AD) 53 2.7.5 Optimisation of HPLC-AD amperometric response under varying pH 53 2.7.6 Calibration standards (pure substances): 54 2.7.7 Specificity standards 55 2.7.8 Accuracy of the study 55 2.7.9 Street samples 55 2.8 Detection and quantification of (±)-mexedrone and (±)- mephedrone 56 2.8.1 Characterisation 56 2.8.2 Preparation of solution to determine λmax: 57 2.8.3 Sample preparation for HPLC method development: 57 2.8.4 Optimisation of potential for amperometric detection (AD) 57 2.8.5 Optimisation of linear velocity for amperometric detection (AD) 58 2.8.6 Optimisation of HPLC-AD amperometric response under varying pH 58 2.8.7 Calibration standards (pure substances): 59 2.8.8 Specificity standards of HPLC-UV 59 2.8.9 Selectivity study of HPLC-UV 59 2.8.10 Accuracy study 60 2.8.11 Street samples 60 2.9 Detection and quantification of (±)-2-MEP, (±)-3-MEP and (±)-4-MEP. 60 2.9.1 Preparation of solutions to determine λmax 60 2.9.2 Sample preparation for HPLC method development 61 2.9.3 Optimisation of potential for amperometric detection (AD) 61 2.9.4 Optimisation of linear velocity for amperometric detection (AD) 61 2.9.5 Optimisation of HPLC-AD amperometric response under varying pH 61 2.9.6 Calibration standards (pure substances): 62 2.9.7 Specificity standards 63 2.9.8 Accuracy of the study 63 2.9.9 Street samples: 63 VII 2.10 Detection and quantification of (±)-2-FEP, (±)-3-FEP and (±)-4-FEP. 64 2.10.1 Preparation of solutions to determine λmax 64 2.10.2 Sample preparation for HPLC method development: 64 2.10.3 Optimisation of potential for amperometric detection (AD) 64 2.10.4 Optimisation of linear velocity for amperometric detection (AD) 65 2.10.5 Optimisation of HPLC-AD amperometric response under varying pH 65 2.10.6 Calibration standards (pure substances): 66 2.10.7 Specificity standards 66 2.10.8 Accuracy of the study 66 2.10.9 Street samples 67 2.11 HPLC-UV validation 67 2.12 Amperometric detection validation: 67 3 Chapter 3: Detection and quantification of (±)-MDMA in the presence of (±)-MA and (±)-PMA by using high- performance liquid chromatography-amperometric detection (HPLC-AD) 68 3.1 Introduction 68 3.2 Ultraviolet-visible spectroscopy (UV) Determination of λmax 72 3.3 HPLC Method Development 72 3.4 Amperometric detection method development 74 3.4.1 Optimisation of the potential of amperometric detection: 74 3.4.2 Optimisation of the linear velocity of amperometric detection 77 3.4.3 Optimisation of pH of HPLC-UV and amperometric detection: 78 3.5 HPLC-AD
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