NDMA Formation by Chloramination of Ranitidine: Kinetics and Mechanism

Julien Le Roux 1 Hervé Gallard 2 Jean-Philippe Croué 2 Sébastien Papot 3 Marie Deborde 4, 3
1 LEESU - Laboratoire Eau Environnement et Systèmes Urbains
2 LCME - Laboratoire de Chimie et Microbiologie de l'Eau
3 IC2MP - Institut de Chimie des Milieux et Matériaux de Poitiers
4 Univ Poitiers, Fac Med & Pharm
Abstract : The kinetics of decomposition of the pharmaceutical ranitidine (a major precursor of NDMA) during chloramination was investigated and some decomposition by-products 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 by-products 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 by-products that are critical intermediates involved in the formation of NDMA, e.g. 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.
Keywords : NDMA Nitrosamine Chloramination Disinfection By-products Ranitidine
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Article dans une revue
Environmental Science and Technology, American Chemical Society, 2012, 46 (20), http://pubs.acs.org/doi/full/10.1021/es3023094. 〈10.1021/es3023094〉
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Julien Le Roux, Hervé Gallard, Jean-Philippe Croué, Sébastien Papot, Marie Deborde. NDMA Formation by Chloramination of Ranitidine: Kinetics and Mechanism. Environmental Science and Technology, American Chemical Society, 2012, 46 (20), http://pubs.acs.org/doi/full/10.1021/es3023094. 〈10.1021/es3023094〉. 〈hal-01201597〉

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