Photodegradation study of three dipyrone metabolites in various water systems: Identification and toxicity of their photodegradation products

Gómez, María José; Sirtori, Carla; Mezcúa, Milagros; Fernández‐Alba, Amadeo R.; Agüera, Ana

doi:10.1016/j.watres.2008.01.022

Cited by 113 publications

(64 citation statements)

References 25 publications

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“…The efficacy of the combination of LC/Q-TOF MS/MS and GC/MS techniques in identification of unknown byproducts has been demonstrated (Gómez et al, 2008). The LC/Q-TOF MS/MS chromatograms show that both direct ozonation and O 3 /H 2 O 2 yielded several degradation byproducts of alachlor (i.e., compounds I-V).…”

Section: Identification Of Hmw Degradation Byproductsmentioning

confidence: 99%

Degradation mechanism of alachlor during direct ozonation and O3/H2O2 advanced oxidation process

et al. 2010

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a b s t r a c tThe degradation of alachlor by direct ozonation and advanced oxidation process O 3 /H 2 O 2 was investigated in this study with focus on identification of degradation byproducts. The second-order reaction rate constant between ozone and alachlor was determined to be 2.5 ± 0.1 M À1 s À1 at pH 7.0 and 20°C. Twelve and eight high-molecular-weight byproducts (with the benzene ring intact) from alachlor degradation were identified during direct ozonation and O 3 /H 2 O 2 , respectively. The common degradation byproducts included N-(2,6-diethylphenyl)-methyleneamine, 8-ethyl-3,4-dihydro-quinoline, 8-ethyl-quinoline, 1-chloroacetyl-2-hydro-3-ketone-7-acetyl-indole, 2-chloro-2 0 ,6 0 -diacetyl-N-(methoxymethyl)acetanilide, 2-chloro-2 0 -acetyl-6 0 -ethyl-N-(methoxymethyl)-acetanilide, and two hydroxylated alachlor isomers. In direct ozonation, four more byproducts were also identified including 1-chloroacetyl-2,3-dihydro-7-ethyl-indole, 2-chloro-2 0 ,6 0 -ethyl-acetanilide, 2-chloro-2 0 ,6 0 -acetyl-acetanilide and 2-chloro-2 0 -ethyl-6 0 -acetyl-N-(methoxymethyl)-acetanilide. Degradation of alachlor by O 3 and O 3 /H 2 O 2 also led to the formation of low-molecular-weight byproducts including formic, acetic, propionic, monochloroacetic and oxalic acids as well as chloride ion (only detected in O 3 /H 2 O 2 ). Nitrite and nitrate formation was negligible. Alachlor degradation occurred via oxidation of the arylethyl group, N-dealkylation, cyclization and cleavage of benzene ring. After O 3 or O 3 /H 2 O 2 treatment, the toxicity of alachlor solution examined by the Daphnia magna bioassay was slightly reduced.

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Section: Identification Of Hmw Degradation Byproductsmentioning

confidence: 99%

Degradation mechanism of alachlor during direct ozonation and O3/H2O2 advanced oxidation process

et al. 2010

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“…Moreover, parent pharmaceuticals of the metabolites selected were also included in the method as they might not be completely metabolized (Jjemba 2006;Mompelat et al 2009). The parent compounds clofibrate, fenofibrate and dipyrone were not considered because they are pro-drugs (Gómez et al 2008;Mompelat et al 2009) and therefore, they are not expected to be found in the aquatic environment.…”

Section: Introductionmentioning

confidence: 99%

Investigation of pharmaceutical metabolites in environmental waters by LC-MS/MS

Gracia-Lor

Ibáñez

Zamora

et al. 2014

Environ Sci Pollut Res

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Pharmaceuticals, once ingested, are commonly metabolized in the body into more polar and soluble forms. These compounds might not be completely removed in the wastewater treatment plants and consequently being discharged into the aquatic ecosystem. In this work, a multi-class sensitive method for the analysis of 21 compounds, including 7 widely consumed pharmaceuticals and 14 relevant metabolites, has been developed based on the use of UHPLC-MS/MS in selected reaction monitoring (SRM) mode. The method was validated in six surface waters (SW) and six effluent wastewaters (EWW) at realistic concentration levels that can be found in waters. The optimized method was applied to the analysis of different types of water samples (rivers, lakes and effluent wastewater), detecting nearly all the parent compounds and metabolites investigated in this work. This fact illustrates that not only pharmaceuticals but also their metabolites are commonly present in these types of waters. Analytical research and monitoring programs should be directed not only towards parent pharmaceuticals but also towards relevant metabolites to have a realistic overview of the impact of pharmaceuticals in the aquatic environment.

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“…Metamizole (also known as dipyrone) is a non-steroidal anti-inflammatory drug. In some countries such as Sweden, UK, Canada or United States metamizole has been banned or restricted for human use due to its association with diseases like agranulocytosis (Gómez et al, 2008). However in many other countries including Spain and Italy it can be purchased without a medical prescription ("Metamizolo: una lunga storia tra luci ed ombre," n.d.).…”

Section: Comparison Of Results From Spain and Italymentioning

confidence: 99%

Screening of pharmaceuticals and illicit drugs in wastewater and surface waters of Spain and Italy by high resolution mass spectrometry using UHPLC-QTOF MS and LC-LTQ-Orbitrap MS

et al. 2015

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Abstract:The existence of pharmaceuticals and illicit drugs (PIDs) in environmental waters has led many analytical chemists to develop screening methods for monitoring purposes.Water samples can contain a huge number of possible contaminants, commonly at low concentrations, which makes their detection and identification problematic. Liquid chromatography coupled with high resolution mass spectrometry (LC-HRMS) has proven itself effective in the screening of environmental contaminants. The present work investigates the use of the most popular HRMS instruments, quadrupole time-offlight and linear trap quadrupole-Orbitrap, from two different laboratories. A suspect screening for PIDs was carried out on wastewater (influent and effluent) and surface water samples from Castellón, Eastern Spain, and Cremona, Northern Italy, incorporating a database of 107 PIDs (including 220 fragment ions). A comparison between the findings of both instruments and of the samples was made which highlights the advantages and drawbacks of the strategies applied in each case. In total, 28 compounds were detected and/or identified by either/both instruments with irbesartan, valsartan, benzoylecgonine and caffeine being the most commonly found compounds across all samples.

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Photodegradation study of three dipyrone metabolites in various water systems: Identification and toxicity of their photodegradation products

Cited by 113 publications

References 25 publications

Degradation mechanism of alachlor during direct ozonation and O3/H2O2 advanced oxidation process

Degradation mechanism of alachlor during direct ozonation and O3/H2O2 advanced oxidation process

Investigation of pharmaceutical metabolites in environmental waters by LC-MS/MS

Screening of pharmaceuticals and illicit drugs in wastewater and surface waters of Spain and Italy by high resolution mass spectrometry using UHPLC-QTOF MS and LC-LTQ-Orbitrap MS

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