Abstract
Novel substances of expected doping activity are constantly introduced to the market. β-Methylphenethylamine (BMPEA) is classified as a doping agent by the World Anti-Doping Agency as it is a positional isomer of amphetamine. In this work, the development and application of a simple and rapid analytical procedure that enables discrimination between both isomers is described. The analytes of interest were extracted from urine by a two-step liquid–liquid extraction and then analyzed by UPLC/MS/MS under isocratic conditions. The entire analytical procedure was validated by evaluating its selectivity, discrimination capabilities, carry-over, sensitivity, and influence of matrix effects on its performance. Application of the method resulted in detection of BMPEA in eight anti-doping samples, including the first report of adverse analytical finding regarding its use. Further analysis showed that BMPEA may be eliminated unchanged along with its phase II conjugates, the hydrolysis of which may considerably improve detection capabilities of the method. Omission of the hydrolysis step may therefore, produce false-negative results. Testing laboratories should also carefully examine their LC/MS/MS-based amphetamine and BMPEA findings as both isomers fragment yielding comparable collision-induced dissociation spectra and their insufficient chromatographic separation may result in misidentification. This is of great importance in case of forensic analyses as BMPEA is not controlled by the public law, and its manufacturing, distribution, and use are legal.
Highlights
In recent years, new doping substances have been" continuously introduced to the market in the form of nutritional supplements
Faculty of Chemistry, Biological and Chemical Research Center, University of Warsaw, Żwirki i Wigury 101, 02-083 Warsaw, Poland analyses as BMPEA is not controlled by the public law, and its manufacturing, distribution, and use are legal
This, in turn, may lead to a large number of sanctioned athletes that fail anti-doping tests once testing laboratories have implemented methods for their detection. This is due to the fact that the list of substances prohibited in sport is open and defines novel doping agents based on their similarity in action and/or structure to those already listed [7, 8]
Summary
New doping substances have been" continuously introduced to the market in the form of nutritional supplements They are often produced in clandestine drug laboratories by modification or positional rearrangement of well-established doping agents such as stimulants [1,2,3]. This, in turn, may lead to a large number of sanctioned athletes that fail anti-doping tests once testing laboratories have implemented methods for their detection This is due to the fact that the list of substances prohibited in sport is open and defines novel doping agents based on their similarity in action and/or structure to those already listed [7, 8]. One of the recent examples is 1,3-dimethylamylamine [9, 10], an isomer of the stimulant tuaminoheptane
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