Stimulants and Doping in Sport
Section snippets
Categories of Stimulants
The class of stimulants prohibited by the World Anti-Doping Agency (WADA)20 contains various agents with different structural features. Many of these compounds are derived from phenethylamine or phenylpropanolamine core structures (Fig. 1) and represent drugs such as amphetamine (1), methamphetamine (2), methylenedioxymethamphetamine (MDMA, ecstasy, 3), or cathine (4), ephedrine (5), and metamfepramone (6). Additional alkaloids with stimulating properties are cocaine (7) and strychnine (8),
Prevalence of stimulants in sport
Stimulants have been a major problem in elite sports and numerous adverse analytical findings (AAFs) have been annually reported by doping control laboratories worldwide. In Table 1, the WADA statistics of 2003 to 2007 are summarized,27 indicating that constantly more than 10% of all AAFs were related to drugs belonging to the class of stimulating agents. In 2003, more than 50% of doping offenses with stimulants were because of ephedrine and its stereoisomer pseudoephedrine. The latter was
Gas Chromatography, Mass Spectrometry/Nitrogen–Phosphorus Specific Detection
Stimulants and alkaloids in general were among the first analytes to be tested in systematic doping controls. In the late 1950s, based on chemistry that provided characteristic and more or less quantitative data by means of color reactions, the capability of gas chromatography (GC) to separate compounds relevant for doping controls was recognized and introduced into sports drug testing to measure various classes of analytes, predominantly sympathomimetic amines.29, 30, 31, 32, 33 Analyzers such
Summary
Stimulants play an important role in sports drug-testing programs. The great variety of compounds belonging to this class of prohibited substances represents a challenge for doping control laboratories, but the sensitive and selective nature of analytical instruments and detection assays has enabled comprehensive screening procedures that not only reveal the misuse but also the presumably unintended intake of banned compounds. Several instances of natural products illegally enriched with
Acknowledgments
The authors thank the Manfred Donike Institute for Doping Analysis, Cologne, for supporting the presented work.
References (68)
A role for physicians in ethnopharmacology and drug discovery
J Ethnopharmacol
(2006)Central nervous system stimulants
Baillieres Best Pract Res Clin Endocrinol Metab
(2000)- et al.
Effect of tuamine, heptaminol and two analogues on uptake and release of catecholamines in cultured chromaffin cells
Biochem Pharmacol
(1990) - et al.
Gas chromatography of sympathomimetic amines
J Pharm Sci
(1962) - et al.
Separation and identification of sympathomimetic amines by gas-liquid chromatography
J Pharm Sci
(1962) N-Methyl-N-trimethylsilyl-trifluoracetamide, ein neues Silylierungsmittel aus der Reihe der silylierten Amide
J Chromatogr
(1969)Acylierung mit Bis(Acylamiden); N-Methyl-Bis(Trifluoracetamid) und Bis(Trifluoracetamid), zwei neue Reagenzien zur Trifluoracetylierung
J Chromatogr
(1973)- et al.
Gas chromatographic detection of nitrogen-containing drugs in aqueous solutions by means of the nitrogen detector
J Chromatogr
(1970) - et al.
Detection in urine of 4-methyl-2-hexaneamine, a doping agent
J Chromatogr B
(2009) - et al.
Clinical and experimental studies with orthoxine in the treatment of bronchial asthma
J Allergy
(1949)
A re-examination of the mono-methoxy positional ring isomers of amphetamine, methamphetamine and phenyl-2-propanone
Forensic Sci Int
Cocaine
Sci Am
Drugs and the athlete
Laser desorption ionization of proteins with molecular masses exceeding 10,000 daltons
Anal Chem
Note sur un Nouvel Alcali
Annales de chimie et de physique
Making the first anti-depressant: amphetamine in American medicine, 1929–1950
J Hist Med Allied Sci
Ueber einige Derivate der Phenylmethacrylsäure und der Phenylisobuttersäure
Berichte der Deutschen Chemischen Gesellschaft
Kanyaku maou seibun kenkyuu seiseki (zoku)
Yakugaku zasshi
The origin of MDMA (ecstasy) revisited: the true story reconstructed from the original documents
Addiction
Physiological effects of the amphetamines during exercise
S Afr Med J
The amphetamine margin in sports
Fed Proc
Centrally-active drugs and performance in sports
Schweiz Z Sportmed
The effect of D-Amphetamine sulfate on physical performance
J Sports Med Phys Fitness
Effect of amphetamine sulfate on athletic performance
J Am Med Assoc
Caffeine and ephedrine: physiological, metabolic and performance-enhancing effects
Sports Med
Pseudoephedrine enhances performance in 1500-m runners
Med Sci Sports Exerc
Amphetamine sulfate and athletic performance. I. Objective effects
J Am Med Assoc
Amphetamine, secobarbital, and athletic performance. III. Quantiative effects on judgment
J Am Med Assoc
Amphetamine, secobarbital, and athletic performance. II. Subjective evaluations of performance, mood states, and physical states
J Am Med Assoc
Pharmacology of stimulants prohibited by the World Anti-Doping Agency (WADA)
Br J Pharmacol
New insights into the mechanism of action of amphetamines
Annu Rev Pharmacol Toxicol
Caffeine and other sympathomimetic stimulants: modes of action and effects on sports performance
Amphetamine induces dopamine efflux through a dopamine transporter channel
Proc Natl Acad Sci U S A
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Simplifying and expanding analytical capabilities for various classes of doping agents by means of direct urine injection high performance liquid chromatography high resolution/high accuracy mass spectrometry
2016, Journal of Pharmaceutical and Biomedical AnalysisCitation Excerpt :In sports drug testing, different initial testing approaches are applied for the determination of stimulants, β2-agonists and narcotics. A common strategy is the separated analysis of volatile and non-volatile compounds using GC–MS(NPD) or LC–MS/MS, respectively [31,32]. In recent years, multiple approaches have been described, combining the analysis of volatile and non-volatile analytes of the aforementioned classes.
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2013, Journal of Chromatography ACitation Excerpt :The pharmacological activity of these compounds including other alkylamines was evaluated decades ago [10–13], but to the best of our knowledge, no pharmacokinetic data are available for these drugs. The detectability of other stimulants is well-known and has been reviewed by several authors [14–17]. Briefly, a combination of liquid chromatography tandem mass spectrometry (LC-QqQ) and gas chromatography–mass spectrometry (GC–MS) appears to be the most suitable technique for the detection of stimulants.
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