Recently, many studies highlighted the consistent finding of irbesartan in effluents from wastewater treatment plants (WWTPs) and in some rivers and lakes in both Europe and North America, suggesting that no >80% can be removed by specific treatments. The present investigation attempts to study the chemical fate of irbesartan in a simulated chlorination step, mimicking the conditions of a WWTP. A total of six disinfection by-products were identified, five were completely new, and separated on a C-18 column by employing a gradient HPLC method. Initially, a complete mass fragmentation pathway of the drug was established with the help of MS/TOF, and subsequently, the disinfection by-products were subjected to MS/TOF mass studies to obtain their mass and fragment pattern. The MS results helped to assign tentative structures to the disinfection products, which were verified through 1D and 2D NMR experiments. The chemical structures of the new compounds have been justified by a proposed mechanism of formation. A preliminary ecotoxicity assessment with the crustacean Daphnia magna showed that some of the identified by-products were up to 12-times more toxic than irbesartan.
Keywords: Acute toxicity test; Chlorination; Daphnia magna; Disinfection by-products; Disinfection treatments; Irbesartan.
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