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. Author manuscript; available in PMC: 2018 Jan 26.
Published in final edited form as: Chem Res Toxicol. 2016 Dec 6;29(12):2194–2205. doi: 10.1021/acs.chemrestox.6b00384

Scheme 3.

Scheme 3

(A) Mechanism of hydrolysis of nitrosamides. Hydrolysis results in a carboxylic acid and an alcohol via a transient diazohydroxide that decomposes to a diazonium ion. (B) The hypothesized decomposition products of CH2-oxo-NNK, CH3-oxo-NNK, and NNC in assay buffer (pH = 7.4) at 37 °C.