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The phenomenon was studied with a model compound, a synthetic <jats:italic>N<\/jats:italic>\u2010hydroxylated tetraamine derivative. It was found that reduction, oxidation and water elimination occurred during APCI to generate the corresponding amine, <jats:italic>N<\/jats:italic>\u2010oxide, and imine. The investigation further revealed that decomposition of hydroxylamines during APCI depends upon the concentration of the analyte and on the acidity of the solution introduced into the ionization source. The pH\u2010dependence of decomposition was utilized for the development of an MS method that allows for the unambiguous identification of N\uf8ffOH functionalities. This method was applied for the study of natural products including polyamine toxins from the venom of the spider <jats:italic>Agelenopsis aperta<\/jats:italic> and mayfoline, a cyclic polyamine derivative of the shrub <jats:italic>Maytenus buxifolia<\/jats:italic>. 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