Abstract
The enantiomeric and diastereomeric profiling of chiral pharmaceuticals (ephedrine, norephedrine, atenolol and venlafaxine) and illicit drugs (amphetamine, methamphetamine, 3,4-methylenedioxyamphetamine (MDA), 3,4-methylenedioxy-N-methylamphetamine (MDMA) and 3,4-methylenedioxy-N-ethylamphetamine (MDEA)) was undertaken over a period of fourteen consecutive days in three wastewater treatment plants (WWTPs) in the city of Valencia, Spain. Degradation efficiency of WWTPs was found to be compound and enantiomer dependent. Selective enantiomer enrichment was observed for several target analytes. Amphetamine and MDMA were enriched with R(−)-enantiomers. 1S,2S(+)-pseudoephedrine was found to be more readily degradable during activated sludge treatment than its diastereomer 1R,2S(−)-ephedrine. Atenolol underwent enrichment with either S(−)- or R(+)-enantiomer in different WWTPs. This unexpected enantiomeric variation in the stereoselective degradation of atenolol could be attributed to different processes utilized during activated sludge treatment. The application of (enantiomeric) profiling of wastewater revealed usage patterns of chiral drugs in the Valencia region.
Highlights
More than 50% of pharmaceuticals and illicit drugs currently in use are chiral (Lien et al, 2006)
Since activity and toxicity of these compounds are often isomerdependent (Kasprzyk-Hordern, 2010), it is of importance to understand the influence of wastewater treatment processes in the selective degradation of chiral drugs in order to improve the performance of wastewater treatment plants (WWTPs) and to protect the receiving aquatic environment
This paper presents for the first time the results of a two week study of three WWTPs in Valencia City and surroundings aiming at estimating the occurrence and stereoselective fate of five chiral pharmaceuticals: and five illicit drugs (amphetamine, methamphetamine, 3,4-methylenedioxyamphetamine (MDA), 3,4-methylenedioxymethamphetamine (MDMA) and 3,4-methylenedioxyethamphetamine (MDEA))
Summary
More than 50% of pharmaceuticals and illicit drugs currently in use are chiral (Lien et al, 2006). They are usually manufactured as racemic compounds, they can be stereoselectively degraded in humans (for example as a result of stereoselective metabolism) and/ or during wastewater treatment as a result of microbial processes. Since activity and toxicity of these compounds are often isomerdependent (Kasprzyk-Hordern, 2010), it is of importance to understand the influence of wastewater treatment processes in the selective degradation of chiral drugs in order to improve the performance of wastewater treatment plants (WWTPs) and to protect the receiving aquatic environment. Specific inter-species toxic effects exist among enantiomers; for example, S(−)-propranolol has a higher chronic toxicity to Fathead Minnows than its enantiomer, but the opposite is true in Daphnia magna (Nikolai et al, 2006)
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