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. Author manuscript; available in PMC: 2021 Aug 17.
Published in final edited form as: Chem Res Toxicol. 2020 Aug 4;33(8):2072–2086. doi: 10.1021/acs.chemrestox.0c00027

Scheme 4.

Scheme 4.

Fragmentation Patterns of NNK Metabolites Showing m/z Values of Protonated Metabolitesa

aThe protonated metabolites are (1, 4) α-hydroxynitrosamines ((M + H)+ = 224.20), (2, 5) α-oxonitrosamines ((M + H)+ = 222.24), (3) 4-oxo-4-(3-pyridyl)butaldehyde ((M + H)+ = 164.19), (6) 4-(3-pyridyl)-4-oxobutane-N-hydroxide ((M + H)+ = 181.19), and (7) 4-amino-1-(3-pyridyl)-1-butanone ((M + H)+ = 165.21), after incubation of 2 mM NNK with enzyme sources, NADPH, and Cu2+.