NDMA formation by chloramination of ranitidine: Kinetics and mechanism
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 monochlor...
| Main Authors: | , , , , |
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| Format: | Journal Article |
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American Chemical Society
2012
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| Online Access: | http://hdl.handle.net/20.500.11937/50189 |
| _version_ | 1848758416766402560 |
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| author | Roux, J. Gallard, H. Croué, Jean-Philippe Papot, S. Deborde, M. |
| author_facet | Roux, J. Gallard, H. Croué, Jean-Philippe Papot, S. Deborde, M. |
| author_sort | Roux, J. |
| building | Curtin Institutional Repository |
| collection | Online Access |
| description | 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. |
| first_indexed | 2025-11-14T09:43:39Z |
| format | Journal Article |
| id | curtin-20.500.11937-50189 |
| institution | Curtin University Malaysia |
| institution_category | Local University |
| last_indexed | 2025-11-14T09:43:39Z |
| publishDate | 2012 |
| publisher | American Chemical Society |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | curtin-20.500.11937-501892017-09-13T15:40:43Z NDMA formation by chloramination of ranitidine: Kinetics and mechanism Roux, J. Gallard, H. Croué, Jean-Philippe Papot, S. Deborde, M. 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 Journal Article http://hdl.handle.net/20.500.11937/50189 10.1021/es3023094 American Chemical Society restricted |
| spellingShingle | Roux, J. Gallard, H. Croué, Jean-Philippe Papot, S. Deborde, M. NDMA formation by chloramination of ranitidine: Kinetics and mechanism |
| title | NDMA formation by chloramination of ranitidine: Kinetics and mechanism |
| title_full | NDMA formation by chloramination of ranitidine: Kinetics and mechanism |
| title_fullStr | NDMA formation by chloramination of ranitidine: Kinetics and mechanism |
| title_full_unstemmed | NDMA formation by chloramination of ranitidine: Kinetics and mechanism |
| title_short | NDMA formation by chloramination of ranitidine: Kinetics and mechanism |
| title_sort | ndma formation by chloramination of ranitidine: kinetics and mechanism |
| url | http://hdl.handle.net/20.500.11937/50189 |