Mass spectrometric characterization of efaproxiral (RSR13) and its implementation into doping controls using liquid chromatography–atmospheric pressure ionization-tandem mass spectrometry

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Abstract

Efaproxiral (2-[4-[[(3,5-dimethylanilino)carbonyl]methyl]phenoxyl]-2-methylpropionic acid, formerly referred to as RSR13) is prohibited in sports according to the World Anti-Doping Agency (WADA). The drug as well as structurally related compounds and a stable isotope-labeled derivative have been synthesized to elucidate the fragmentation pathway of efaproxiral, using electrospray ionization (ESI) and tandem mass spectrometry by employing a novel linear ion trap—orbitrap hybrid mass spectrometer—in positive and negative ionization modes. The elimination of 2-methyl acrylic acid (−86 u) has been identified as a major fragmentation process in both charge states. Negative ionization and collision-induced dissociation (CID) caused an additional release of carbon dioxide (−44 u), and positive ionization the loss of formic acid (−46 u). Efaproxiral was incorporated into an existing screening procedure for doping controls using solid-phase extraction (SPE) followed by liquid chromatography-tandem mass spectrometry, enabling a limit of detection of 2.5 ng/ml and interday precisions ranging from 7.9 to 13.0%. Verf.-Referat
Translated title of the contributionMassenspektrometrische Charakterisierung von Efaproxiral (RSR13) und deren Umsetzung in der Dopingkontrolle unter Verwendung von Flüssigkeitschromatographie/Ionisation bei Atmosphärendruck/Tandem-Massenspektrometrie
Original languageEnglish
JournalJournal of mass spectrometry : JMS
Volume41
Pages (from-to)332-338
Number of pages7
ISSN1076-5174
Publication statusPublished - 2006

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