Related Experiment Video
Updated: Aug 16, 2026

A General Method for Detecting Nitrosamide Formation in the In Vitro Metabolism of Nitrosamines by Cytochrome P450s
Published on: September 25, 2017
Compound screening for the presence of the primary N-oxide functionality via ion-molecule reactions in a mass
Michael A Watkins1, Danielle V WeWora, Sen Li
1Department of Chemistry, Purdue University, West Lafayette, IN 47907-2038, USA.
Abstract:
A mass spectrometry method is presented for the identification of compounds that contain the primary N-oxide functional group. This method utilizes a gas-phase ion-molecule reaction with dimethyl disulfide that rapidly and selectively derivatizes the protonated primary N-oxide functional group in a mass spectrometer to yield an ionic reaction product (with 31 Da higher mass than that of the protonated molecule) that is diagnostic for the presence of a primary N-oxide functionality. A variety of protonated analytes containing different functional groups were tested in Fourier transform ion-cyclotron resonance and triple quadrupole mass spectrometers to probe the selectivity of the reaction. Only molecules containing the protonated primary N-oxide functional group yielded the diagnostic reaction product; all other protonated molecules gave protonated dimethyl disulfide or no reaction products. The feasibility of this method for compound screening was tested by examining six analytes with the same molecular formula but different atom connectivity. The one analyte that contained the primary N-oxide functional group was readily differentiated from the other analytes.
More Related Videos
05:48Analysis of Volatile and Oxidation Sensitive Compounds Using a Cold Inlet System and Electron Impact Mass Spectrometry
Published on: September 5, 2014
13:21Detection of Nitric Oxide and Superoxide Radical Anion by Electron Paramagnetic Resonance Spectroscopy from Cells using Spin Traps
Published on: August 18, 2012
Related Concept Videos
Mass Spectrum: Interpretation
Mass Spectrometers
Mass Spectrometry: Overview
Mass Spectrometry of Amines
Chemical Ionization (CI) Mass Spectrometry
2° Amines to N-Nitrosamines: Reaction with NaNO2