WADA: Synthesis of Mesocarb Metabolites as Reference Compounds for Doping Analytics

Project Details


Mesocarb (Sydnocarb®) is an amphetamine-related psychostimulant that has been used for doping purposes due to its central nervous system stimulating effects. Moreover, it is very likely that mesocarb is being used by drug addicts. Mesocarb is included in the World Anti-Doping Agency’s list of substances and methods that are prohibited in sports. Mesocarb is chemically a cyclic and mesoionic N-phenylcarbamoyl-3-(beta-phenylisopropyl)sydnone imine. The dominant urinary metabolites of mesocarb are identified to be its mono-, di- and trihydroxylated isomers. The exact chemical structures of regioisomeric metabolites of mesocarb have not been solved yet. Furthermore, the metabolites are not commercially available. According to the WADA’s international laboratory standard and ISO 17025 standard, well characterized pure reference materials are recommended to be used as references in the analysis.
In this project a high-yielding and selective synthesis methods for the preparation of mesocarb metabolites as reference substances will be developed. The synthesized metabolites will be purified and characterized and their chemical stability will be tested. The synthesized substan-ces will be used to solve so far unknown regiochemical structures of the main urinary metaboli-tes of mesocarb. Using the synthesized substances, the feasibility of various screening methods used in doping laboratories for the abuse of mesocarb will be tested, and a liquid chromatographic – tandem mass spectrometric confirmation method will be developed and validated. Finally, the synthesized mesocarb metabolites would be available free of charge as reference substances to the world’s antidoping community. The pure and fully characterized reference substances would enable the reliable and legally defensible analysis of mesocarb and could also be used in quality assurance and in development of new analytical methods.
Effective start/end date01/01/200631/12/2007