NDMA formation by chloramination of ranitidine: Kinetics and mechanism
MetadataShow full item record
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.
PublisherAmerican Chemical Society (ACS)
- Formation of NDMA from ranitidine and sumatriptan: the role of pH.
- Authors: Shen R, Andrews SA
- Issue date: 2013 Feb 1
- Reduction of N-nitrosodimethylamine formation from ranitidine by ozonation preceding chloramination: influencing factors and mechanisms.
- Authors: Zou R, Liao X, Zhao L, Yuan B
- Issue date: 2018 May
- The role of chloramine species in NDMA formation.
- Authors: Selbes M, Beita-Sandí W, Kim D, Karanfil T
- Issue date: 2018 Sep 1
- Characterization of N-nitrosodimethylamine formation from the ozonation of ranitidine.
- Authors: Lv J, Wang L, Li Y
- Issue date: 2017 Aug
- Chloramination of nitrogenous contaminants (pharmaceuticals and pesticides): NDMA and halogenated DBPs formation.
- Authors: Le Roux J, Gallard H, Croué JP
- Issue date: 2011 May