Degradation pathways of lamotrigine under advanced treatment by direct UV photolysis, hydroxyl radicals, and ozone

Keen, Olya S.; Ferrer, Imma; Thurman, E. Michael; Linden, Karl G.

doi:10.1016/j.chemosphere.2014.07.085

Cited by 37 publications

(26 citation statements)

References 39 publications

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“…The lamotrigine molecule is composed of a 1,2,4-triazine ring with two substituting amine groups attached to 2,3-dichlorobenzene (Table S1). Abiotic transformation of lamotrigine occurs mainly on the triazine ring, as was demonstrated by applying electrochemistry, photo-oxidation, and ozonation, and confirmed by mass spectrometry (MS). ,− The triazine ring is susceptible to electrophilic attacks because of its electron enrichment by substituting amine groups. Lamotrigine’s benzene moiety is relatively deactivated by two electron-withdrawing chlorine atoms.…”

Section: Introductionmentioning

confidence: 91%

Abiotic Transformation of Lamotrigine by Redox-Active Mineral and Phenolic Compounds

Karpov

Seiwert

Mordehay

et al. 2021

Environ. Sci. Technol.

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The anticonvulsant drug lamotrigine is a recalcitrant environmental pollutant. It was detected in drinking water, surface water, reclaimed wastewater, arable soils, and even in edible crops. In this work, we studied the mechanisms of lamotrigine transformation by a common redox soil mineral, birnessite, in a single-solute system and in bisolute systems with vanillic acid or o-methoxyphenol. In the single-solute system, 28% of lamotrigine was transformed and 14 transformation products (TPs) were identified. Based on a detailed analysis of the TPs, we suggested that lamotrigine is transformed mainly by oxidation, addition, and dechlorination reactions. In the bisolute systems, the redox-active phenolic compounds enhanced the elimination and transformation of lamotrigine. Vanillic acid was more efficient, generating 92% transformation of lamotrigine (58 TPs were identified), whereas o-methoxyphenol induced 48% transformation (35 TPs were identified). In the bisolute system with phenolic compounds, lamotrigine has possibly been transformed mainly via addition reactions with phenolic compounds and their oxidation products (protocatechuic acid, quinone, and oligomers). Thus, masses of the formed TPs were elevated as compared to the parent compound. The current study demonstrates the important role of redox-active minerals and naturally occurring phenolic compounds in abiotic removal and transformation of a recalcitrant environmental pollutant.

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Section: Introductionmentioning

confidence: 91%

Abiotic Transformation of Lamotrigine by Redox-Active Mineral and Phenolic Compounds

Karpov

Seiwert

Mordehay

et al. 2021

Environ. Sci. Technol.

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“…Lamotrigine is very persistent chemically and physically and can resist UV photolysis and ozone, but it reacts rapidly with hydroxyl radicals. Therefore, advanced oxidation processes might be effective for removing this compound during water treatment [40]. In this study, 46.4% of lamotrigine was removed by ozone purification with the OxTube hermetic dissolution method.…”

Section: Lamotriginementioning

confidence: 99%

Presence and Reduction of Anthropogenic Substances with UV Light and Oxidizing Disinfectants in Wastewater—A Case Study at Kuopio, Finland

Ikonen

Nuutinen

Niittynen

et al. 2021

Water

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Anthropogenic substances are a major concern due to their potential harmful effects towards aquatic ecosystems. Because wastewater treatment plants (WWTPs) are not designed to remove these substances from wastewater, a part of the anthropogenic substances enter nature via WWTP discharges. During the spring 2019, the occurrence of anthropogenic substances in the municipal wastewater effluent in Kuopio, Finland, was analysed. Furthermore, the capacity of selected disinfection methods to reduce these substances from wastewater was tested. The disinfection methods were ozonation (760 mL min−1) with an OxTube hermetic dissolution method (1), the combined usage of peracetic acid (PAA) (<5 mg L−1) and ultraviolet (UV) disinfection (12 mJ/cm2) (2), and the combined usage of hydrogen peroxide (H2O2) (<10 mg L−1) and UV disinfection (12 mJ/cm2) (3). The substances found at the concentrations over 1 µg L−1 in effluent (N = 3) were cetirizine (5.2 ± 1.3 µg L−1), benzotriazole (BZT) (2.1 ± 0.98 µg L−1), hydrochlorothiazide (1.7 ± 0.2 µg L−1), furosemide (1.6 ± 0.2 µg L−1), lamotrigine (1.5 ± 0.06 µg L−1), diclofenac (DCF) (1.4 ± 0.2 µg L−1), venlafaxine (1.0 ± 0.13 µg L−1) and losartan (0.9 ± 0.2 µg L−1). The reduction (%) with different methods (1, 2, 3) were: cetirizine (99.9, 5.0, NR = no removal), benzotriazole (67.9, NR, NR), hydrochlorothiazide (91.1, 5.9, NR), furosemide (99.7, 5.9, NR), lamotrigine (46.4, NR, 6.7), diclofenac (99.7, 7.1, 16.7), venlafaxine (91.3, NR, 1.1), losartan (99.6, 13.8, NR). Further research concerning the tested disinfection methods is needed in order to fully elucidate their potential for removing anthropogenic substances from purified wastewater.

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“…Photodegradation. The anticonvulsant lamotrigine's degradation with UV, ozone, and hydroxyl radicals were investigated by Keen et al 94 It was observed that lamotrigine was stable under UV and ozone treatments, but degraded in the presence of hydroxyl radicals, so advanced oxidation processes would be the most optimal choice for treatment. The transformation pathway and products were determined with LC−TOF-MS.…”

Section: Analytical Chemistrymentioning

confidence: 99%

Water Analysis: Emerging Contaminants and Current Issues

2015

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Degradation pathways of lamotrigine under advanced treatment by direct UV photolysis, hydroxyl radicals, and ozone

Cited by 37 publications

References 39 publications

Abiotic Transformation of Lamotrigine by Redox-Active Mineral and Phenolic Compounds

Abiotic Transformation of Lamotrigine by Redox-Active Mineral and Phenolic Compounds

Presence and Reduction of Anthropogenic Substances with UV Light and Oxidizing Disinfectants in Wastewater—A Case Study at Kuopio, Finland

Water Analysis: Emerging Contaminants and Current Issues

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