N-dealkylation of amines during water disinfection – Revealing a new direction in the formation of disinfection by-products

Mazur, D.M.; Surmillo, A.S.; Sypalov, S.A.; Varsegov, I.S.; Ul'yanovskii, N.V.; Kosyakov, D.S.; Lebedev, A.T.

doi:10.1016/j.chemosphere.2024.141117

Cited by 2 publications

(1 citation statement)

References 33 publications

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“…Along with cyclization, the most important direction of BRO transformation is Ndealkylation. The possibility of such transformations as a result of one-electron transfer was confirmed in a recent study [39]. In the case of bromhexine, the loss of the methyl or cyclohexyl substituents, as well as their consecutive elimination, can occur.…”

Section: Primary Transformations Of Bromhexinementioning

confidence: 77%

Mucolytic Drugs Ambroxol and Bromhexine: Transformation under Aqueous Chlorination Conditions

Sypalov,

Varsegov,

Ulyanovskii

et al. 2024

IJMS

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Bromhexine and ambroxol are among the mucolytic drugs most widely used to treat acute and chronic respiratory diseases. Entering the municipal wastewater and undergoing transformations during disinfection with active chlorine, these compounds can produce nitrogen- and bromine-containing disinfection by-products (DBPs) that are dangerous for aquatic ecosystems. In the present study, primary and deep degradation products of ambroxol and bromhexine obtained in model aquatic chlorination experiments were studied via the combination of high-performance liquid and gas chromatography with high-resolution mass spectrometry. It was shown that at the initial stages, the reactions of cyclization, hydroxylation, chlorination, electrophilic ipso-substitution of bromine atoms with chlorine, and oxidative N-dealkylation occur. Along with known metabolites, a number of novel primary DBPs were tentatively identified based on their elemental compositions and tandem mass spectra. Deep degradation of bromhexine and ambroxol gives twenty-four identified volatile and semi-volatile compounds of six classes, among which trihalomethanes account for more than 50%. The specific class of bromhexine- and ambroxol-related DBPs are bromine-containing haloanilines. Seven of them, including methoxy derivatives, were first discovered in the present study. One more novel class of DBPs associated with bromhexine and ambroxol is represented by halogenated indazoles formed through dealkylation of the primary transformation products containing pyrazoline or tetrahydropyrimidine cycle in their structure.

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Section: Primary Transformations Of Bromhexinementioning

confidence: 77%

Mucolytic Drugs Ambroxol and Bromhexine: Transformation under Aqueous Chlorination Conditions

Sypalov,

Varsegov,

Ulyanovskii

et al. 2024

IJMS

Self Cite

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Semiconductor Effect from Pd(II) Porphyrin Metal to Its Ligand in Photocatalytic N‐Dealkylation

Liao,

Gao,

Weng

et al. 2024

ChemSusChem

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In this work, four saddled Pd(II) porphyrins were developed as photocatalyst for N‐dealkylation of triethyl Rhodamine (TER) under visible light, and their catalytic ability was found to be negatively related to the out‐of‐plane of their macrocycles. Two important relationships involving the metalloporphyrins as catalyst were revealed: (1) a photoexcitative semiconductor effect between the 4dx2‐ᵧ2(Pd) and a2u(π) orbitals of Pd(II) porphyrin on the dealkylation. (2) a domino process from strap length, ring geometry, core deformation, d‐π gap variation, to photocatalytic activity. Two revelations imply a unidirectional electron transfer route from axial ligand, to central metal, to porphyrin ring based on photoexcitation and guide the design and development of complex photocatalysts, and their revelation is attributed to the acquisition of a series of Pd(II) porphyrins with continuous ring distortion. The findings help to understand the photocatalytic single electron transfer (SET)‐first mechanism based on metallic complex.

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N-dealkylation of amines during water disinfection – Revealing a new direction in the formation of disinfection by-products

Cited by 2 publications

References 33 publications

Mucolytic Drugs Ambroxol and Bromhexine: Transformation under Aqueous Chlorination Conditions

Mucolytic Drugs Ambroxol and Bromhexine: Transformation under Aqueous Chlorination Conditions

Semiconductor Effect from Pd(II) Porphyrin Metal to Its Ligand in Photocatalytic N‐Dealkylation

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