NDMA formation by chloramination of ranitidine: Kinetics and mechanism

Handle URI:
http://hdl.handle.net/10754/562367
Title:
NDMA formation by chloramination of ranitidine: Kinetics and mechanism
Authors:
Le Roux, Julien; Gallard, Hervé; Croue, Jean-Philippe; Papot, Sébastien; Deborde, Marie
Abstract:
The kinetics of decomposition of the pharmaceutical ranitidine (a major precursor of NDMA) during chloramination was investigated and some decomposition byproducts were identified by using high performance liquid chromatography coupled with mass spectrometry (HPLC-MS). The reaction between monochloramine and ranitidine followed second order kinetics and was acid-catalyzed. Decomposition of ranitidine formed different byproducts depending on the applied monochloramine concentration. Most identified products were chlorinated and hydroxylated analogues of ranitidine. In excess of monochloramine, nucleophilic substitution between ranitidine and monochloramine led to byproducts that are critical intermediates involved in the formation of NDMA, for example, a carbocation formed from the decomposition of the methylfuran moiety of ranitidine. A complete mechanism is proposed to explain the high formation yield of NDMA from chloramination of ranitidine. These results are of great importance to understand the formation of NDMA by chloramination of tertiary amines. © 2012 American Chemical Society.
KAUST Department:
Biological and Environmental Sciences and Engineering (BESE) Division
Publisher:
American Chemical Society (ACS)
Journal:
Environmental Science & Technology
Issue Date:
16-Oct-2012
DOI:
10.1021/es3023094
PubMed ID:
22967139
Type:
Article
ISSN:
0013936X
Appears in Collections:
Articles; Biological and Environmental Sciences and Engineering (BESE) Division

Full metadata record

DC FieldValue Language
dc.contributor.authorLe Roux, Julienen
dc.contributor.authorGallard, Hervéen
dc.contributor.authorCroue, Jean-Philippeen
dc.contributor.authorPapot, Sébastienen
dc.contributor.authorDeborde, Marieen
dc.date.accessioned2015-08-03T10:02:41Zen
dc.date.available2015-08-03T10:02:41Zen
dc.date.issued2012-10-16en
dc.identifier.issn0013936Xen
dc.identifier.pmid22967139en
dc.identifier.doi10.1021/es3023094en
dc.identifier.urihttp://hdl.handle.net/10754/562367en
dc.description.abstractThe kinetics of decomposition of the pharmaceutical ranitidine (a major precursor of NDMA) during chloramination was investigated and some decomposition byproducts were identified by using high performance liquid chromatography coupled with mass spectrometry (HPLC-MS). The reaction between monochloramine and ranitidine followed second order kinetics and was acid-catalyzed. Decomposition of ranitidine formed different byproducts depending on the applied monochloramine concentration. Most identified products were chlorinated and hydroxylated analogues of ranitidine. In excess of monochloramine, nucleophilic substitution between ranitidine and monochloramine led to byproducts that are critical intermediates involved in the formation of NDMA, for example, a carbocation formed from the decomposition of the methylfuran moiety of ranitidine. A complete mechanism is proposed to explain the high formation yield of NDMA from chloramination of ranitidine. These results are of great importance to understand the formation of NDMA by chloramination of tertiary amines. © 2012 American Chemical Society.en
dc.publisherAmerican Chemical Society (ACS)en
dc.titleNDMA formation by chloramination of ranitidine: Kinetics and mechanismen
dc.typeArticleen
dc.contributor.departmentBiological and Environmental Sciences and Engineering (BESE) Divisionen
dc.identifier.journalEnvironmental Science & Technologyen
dc.contributor.institutionUniversité de Poitiers - CNRS, UMR 7285 IC2MP - ENSIP, 1 rue Marcel Doré, 86022 Poitiers Cedex, Franceen
dc.contributor.institutionUniversité de Poitiers - CNRS, UMR 7285 IC2MP, 4 rue Michel Brunet, 86022 Poitiers Cedex, Franceen
kaust.authorCroue, Jean-Philippeen
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