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      Comparison of 3 Derivatization Methods for the Analysis of Amphetamine-Related Drugs in Oral Fluid by Gas Chromatography-Mass Spectrometry

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      Analytical Chemistry Insights

      SAGE Publications

      Amphetamine, drugs, oral fluids, gas chromatography, analysis

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          Abstract

          The heptafluorobutyric anhydride (HFBA), pentafluoropropionic anhydride (PFPA), and trifluoroacetic anhydride (TFAA) are compared as derivatizing reagents to use as the optimal method for the analysis of 10 amphetamines and cathinones in oral fluid. The target compounds were amphetamine (AMP), methamphetamine (MA), 4-methylamphetamine, 3,4-methylenedioxyamphetamine (MDA), 3,4-methylenedioxymethamphetamine (MDMA), 3,4-methylenedioxy- N-ethylamphetamine (MDEA), cathinone (CAT), methcathinone, mephedrone, and ephedrine. Amphetamine-D 5, MA-D 5, MDA-D 5, MDMA-D 5, and MDEA-D 5 use as internal standards (IS). The analytes and IS were extracted from 0.5 mL of oral fluid by ethyl acetate in the presence of NaOH (0.1 N) as the base and then the dried extracts were derivatized with HFBA, PFPA, or TFAA at 70°C for 30 minutes. The limits of quantification based on signal-to-noise ratios ≥10 were ranged between 2.5 and 10 ng/mL. The calibration graphs were linear in the range of 5 or 10 to 1000 ng/mL for all analytes. Based on sensitivity, the PFPA is proved to be the best for derivatization of the target compounds prior to gas chromatography-mass spectrometry analysis.

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          Most cited references 32

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          Toxicity of amphetamines: an update.

          Amphetamines represent a class of psychotropic compounds, widely abused for their stimulant, euphoric, anorectic, and, in some cases, emphathogenic, entactogenic, and hallucinogenic properties. These compounds derive from the β-phenylethylamine core structure and are kinetically and dynamically characterized by easily crossing the blood-brain barrier, to resist brain biotransformation and to release monoamine neurotransmitters from nerve endings. Although amphetamines are widely acknowledged as synthetic drugs, of which amphetamine, methamphetamine, and 3,4-methylenedioxymethamphetamine (MDMA, ecstasy) are well-known examples, humans have used natural amphetamines for several millenniums, through the consumption of amphetamines produced in plants, namely cathinone (khat), obtained from the plant Catha edulis and ephedrine, obtained from various plants in the genus Ephedra. More recently, a wave of new amphetamines has emerged in the market, mainly constituted of cathinone derivatives, including mephedrone, methylone, methedrone, and buthylone, among others. Although intoxications by amphetamines continue to be common causes of emergency department and hospital admissions, it is frequent to find the sophism that amphetamine derivatives, namely those appearing more recently, are relatively safe. However, human intoxications by these drugs are increasingly being reported, with similar patterns compared to those previously seen with classical amphetamines. That is not surprising, considering the similar structures and mechanisms of action among the different amphetamines, conferring similar toxicokinetic and toxicological profiles to these compounds. The aim of the present review is to give an insight into the pharmacokinetics, general mechanisms of biological and toxicological actions, and the main target organs for the toxicity of amphetamines. Although there is still scarce knowledge from novel amphetamines to draw mechanistic insights, the long-studied classical amphetamines-amphetamine itself, as well as methamphetamine and MDMA, provide plenty of data that may be useful to predict toxicological outcome to improvident abusers and are for that reason the main focus of this review.
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            Cathinone derivatives: a review of their chemistry, pharmacology and toxicology.

             John P Kelly (2015)
            The purpose of this review is to evaluate what is currently known about the pharmacology of cathinone derivatives. Cathinone is the principal active constituent of khat responsible for the stimulant effects that have led khat to be known as a 'natural amphetamine'. Synthetic derivatives have been abused for their amphetamine-like stimulant effects, most notably methylone, methcathinone (ephedrone), and 4-methlymethcathinone (mephedrone). To date, cathinone and methcathinone have been studied most, demonstrating amphetamine-like effects in a range of in vitro and in vivo investigations, albeit less potently than amphetamines. In humans, cathinone derivatives are usually administered orally, and in some cases by insufflation. Methcathinone has a longer history of abuse, being produced from readily available starting materials, and administered by injection. Mephedrone has become the best publicised cathinone derivative, amid considerable media and public concern about its legal status, its ready availability, and reports of serious toxicity and deaths following its use. As a consequence, there has been a clampdown on cathinone derivatives, dramatically changing their legal status in a number of countries. However, little objective evidence-based comparative experiments have been conducted to date between these compounds and their related amphetamines in order to make clear risk judgements. Such assessments have largely been predictive in nature, based on their structural similarity to amphetamines. It can be assumed that, despite their illegal status, cathinone-related compounds will continue to be prevalent drugs of abuse for the foreseeable future. Copyright © 2011 John Wiley & Sons, Ltd.
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              Ephedra in perspective--a current review.

              Although the traditional use of Ephedra 'ma huang' has been established for thousands of years, its resurgence in the US as a herbal dietary supplement is currently a matter of national controversy. At the heart of the debate are three important questions: (1) the identity and composition of Ephedra products with regard to ephedrine and related alkaloids; (2) the potential therapeutic utility of Ephedra supplements for weight loss or performance enhancement; and (3) potential health risks associated with such uses of Ephedra, particularly in sensitive individuals or in cases of intentional abuse for its stimulant properties. This review surveys the literature on Ephedra with regard to traditional uses, botany, chemistry, analytics, pharmacological effects and health risks. A brief discussion of the central issues in the current debate on the regulation of Ephedra in the United States is included as this is where most of the problems have occurred to date. Copyright 2003 John Wiley & Sons, Ltd.
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                Author and article information

                Journal
                Anal Chem Insights
                Anal Chem Insights
                ACI
                spaci
                Analytical Chemistry Insights
                SAGE Publications (Sage UK: London, England )
                1177-3901
                24 August 2017
                2017
                : 12
                Affiliations
                The Department of Forensic Chemistry, The College of Forensic Sciences, Naif Arab University for Security Sciences, Riyadh, Saudi Arabia
                Author notes
                Khaled M Mohamed, The Department of Forensic Chemistry, The College of Forensic Sciences, Naif Arab University for Security Sciences, Riyadh, Saudi Arabia. Email: khaled.masoud@ 123456yahoo.com
                Article
                10.1177_1177390117727533 ACI-0042332
                10.1177/1177390117727533
                5574487
                © The Author(s) 2017

                This article is distributed under the terms of the Creative Commons Attribution-NonCommercial 4.0 License ( http://www.creativecommons.org/licenses/by-nc/4.0/) which permits non-commercial use, reproduction and distribution of the work without further permission provided the original work is attributed as specified on the SAGE and Open Access page( https://us.sagepub.com/en-us/nam/open-access-at-sage).

                Categories
                Original Research
                Custom metadata
                January-December 2017

                Analytical chemistry

                amphetamine, drugs, oral fluids, gas chromatography, analysis

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