title: Fate of the drug chlorpromazine in river water according to laboratory assays. Identification and evolution over time of degradation products. Sorption to sediment.
abstract: Toxic effects of the non-biodegradable drug chlorpromazine and its degradation products have been reported on microorganisms in aqueous media. Here, chlorpromazine degradation assays in forced and non-forced conditions have been done to know its persistence and degradation products in river water. Sunlight irradiation promotes the complete degradation of chlorpromazine (2 μg L(-1)) in less than 4 h, but if the exposure to sunlight is limited chlorpromazine is detected during 4 weeks in river water. Sixteen degradation products in surface water are described for first time after solid-phase extraction and analysis by ultra-pressure liquid chromatography/quadrupole time-of-flight/mass spectrometry; their structures are proposed from the molecular formulae of the fragment-ions observed in high-resolution tandem mass spectra. Hydroxylation and oxidation products such as chlorpromazine sulfoxide, 2-hydroxypromazine and 2-hydroxypromazine sulfoxide were predominant degradation products in the early stages; some benzo[1,4]thiazin-6-ol derivatives resulting from the breakdown of the phenothiazine core were the major and relatively stable products after 20 weeks under non-forced conditions. A degradation pathway of chlorpromazine in water is outlined. Moreover, it is shown that chlorpromazine is very strongly adsorbed on sediment while the degradation products that kept the promazine core have a notable capacity of sorption, too; sorption coefficients are calculated. Finally, a prediction about the toxicity of the degradation products in aquatic ecosystems suggests that some of them have toxicities similar, or even higher, than chlorpromazine.
authors: Department of Analytical Chemistry, Faculty of Sciences, Campus Miguel Delibes, University of Valladolid, Paseo de Belén 7, 47011 Valladolid, Spain; I.U. CINQUIMA, Campus Miguel Delibes, University of Valladolid, Paseo de Belén 5, 47011 Valladolid, Spain. Electronic address: jjimenez@qa.uva.es.
authors: Juan J
authors: JJ
authors: Jiménez
authors: Department of Analytical Chemistry, School of Industrial Engineers, University of Valladolid, Francisco Mendizábal 1, 47014 Valladolid, Spain.
authors: Beatriz E
authors: BE
authors: Muñoz
authors: Department of Analytical Chemistry, School of Industrial Engineers, University of Valladolid, Francisco Mendizábal 1, 47014 Valladolid, Spain.
authors: María I
authors: MI
authors: Sánchez
authors: Department of Analytical Chemistry, Faculty of Sciences, Campus Miguel Delibes, University of Valladolid, Paseo de Belén 7, 47011 Valladolid, Spain.
authors: Rafael
authors: R
authors: Pardo
authors: Department of Analytical Chemistry, Faculty of Sciences, Campus Miguel Delibes, University of Valladolid, Paseo de Belén 7, 47011 Valladolid, Spain.
authors: María S
authors: MS
authors: Vega
mesh_terms: D065966:Absorption, Physicochemical; D001673:Biodegradation, Environmental; D001681:Biological Assay; D002746:Chlorpromazine / Q000737:chemistry* / Q000378:metabolism; D002853:Chromatography, Liquid / Q000379:methods; D019015:Geologic Sediments / Q000737:chemistry*; D045483:Rivers / Q000737:chemistry*; D052616:Solid Phase Extraction / Q000379:methods; D053719:Tandem Mass Spectrometry / Q000379:methods; D014874:Water Pollutants, Chemical / Q000032:analysis* / Q000737:chemistry* / Q000378:metabolism
chemical_list: D014874:Water Pollutants, Chemical; D002746:Chlorpromazine
keywords: Chlorpromazine; Degradation products; High-resolution mass spectrometry; River water; Sorption coefficients