Mass spectrometric analysis of androstan-17beta-ol-3-one and androstadiene-17beta-ol-3-one isomers

Publication: Contribution to journalJournal articlesResearch


Mass spectrometric identification and characterization of steroids using electrospray ionization and tandem mass spectrometry has advantages in drug testing and doping control analysis attributable to limitations of gas chromatography followed by electron ionization mass spectrometry. Steroids with an androstadiene-17beta-ol-3-one nucleus and double bonds located either at C-1 and C-4, C-4 and C-9, or C-4 and C-6 were used to determine characteristic fragmentation pathways. Diagnostic dissociation routes are proposed using deuterium labeling, MS3 experiments, and analyses of structurally closely related compounds. Steroids such as boldenone (androst-1,4-diene-17beta-ol-3-one) produced characteristic product ions at m/z 121, 135, and 147. Compounds with double bonds at C-4 and C-9 generated abundant product ions at m/z 145 and 147. Conjugated double bonds at C-4 and C-6 gave rise to an intense and characteristic signal at m/z 133. Stereochemical differentiation between 5alpha- and 5beta-isomers of androstan-17beta-ol-3-ones was possible because of significant differences in relative abundance of product ions generated by elimination of acetone from alpha,beta-saturated 3-keto steroids.

Original languageEnglish
JournalJournal of the American Society for Mass Spectrometry
Issue number10
Pages (from-to)1660-1669
Number of pages10
Publication statusPublished - 01.10.2005

Research areas and keywords

  • Androstadienes
  • Androstanes
  • Isomerism
  • Microchemistry
  • Spectrometry, Mass, Electrospray Ionization
  • Substance Abuse Detection


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