Enantiomeric fraction evaluation of pharmaceuticals in environmental matrices by liquid chromatography-tandem mass spectrometry

Ana Rita Ribeiro, Lúcia H.M.L.M. Santos, Alexandra S. Maia, Cristina Delerue-Matos, Paula M.L. Castro, Maria Elizabeth Tiritan*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

54 Citations (Scopus)


The interest for environmental fate assessment of chiral pharmaceuticals is increasing and enantioselective analytical methods are mandatory. This study presents an enantioselective analytical method for the quantification of seven pairs of enantiomers of pharmaceuticals and a pair of a metabolite. The selected chiral pharmaceuticals belong to three different therapeutic classes, namely selective serotonin reuptake inhibitors (venlafaxine, fluoxetine and its metabolite norfluoxetine), beta-blockers (alprenolol, bisoprolol, metoprolol, propranolol) and a beta2-adrenergic agonist (salbutamol). The analytical method was based on solid phase extraction followed by liquid chromatography tandem mass spectrometry with a triple quadrupole analyser. Briefly, Oasis® MCX cartridges were used to preconcentrate 250mL of water samples and the reconstituted extracts were analysed with a Chirobiotic™ V under reversed mode. The effluent of a laboratory-scale aerobic granular sludge sequencing batch reactor (AGS-SBR) was used to validate the method. Linearity (r2>0.99), selectivity and sensitivity were achieved in the range of 20-400ngL-1 for all enantiomers, except for norfluoxetine enantiomers which range covered 30-400ngL-1. The method detection limits were between 0.65 and 11.5ngL-1 and the method quantification limits were between 1.98 and 19.7ngL-1. The identity of all enantiomers was confirmed using two MS/MS transitions and its ion ratios, according to European Commission Decision 2002/657/EC. This method was successfully applied to evaluate effluents of wastewater treatment plants (WWTP) in Portugal. Venlafaxine and fluoxetine were quantified as non-racemic mixtures (enantiomeric fraction≠0.5). The enantioselective validated method was able to monitor chiral pharmaceuticals in WWTP effluents and has potential to assess the enantioselective biodegradation in bioreactors. Further application in environmental matrices as surface and estuarine waters can be exploited.
Original languageEnglish
Pages (from-to)226-235
Number of pages10
JournalJournal of Chromatography A
Publication statusPublished - 10 Oct 2014


  • Chiral pharmaceuticals
  • Chirobiotic V
  • Enantiomeric fraction
  • LC-MS/MS
  • Macrocyclic antibiotic CSP


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