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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 7.

Scheme 7.

Fragmentation Patterns of NNN Metabolitesa

aThe protonated metabolites (and their m/z values) are (1, 5) 2′-hydroxy NNN and 5′-hydroxy NNN ((M + H)+ = 193.09), (2) diazohydroxide ((M + H)+ = 194.19), (3) 4-hydroxyl-1-(3-pyridyl)-1-butanone (HPB, (M + H)+ = 166.08)), (4) 4-oxo-4-(3-pyridyl)-1-butanal (OPB, (M + H)+ = 163.06)), (6) diazohydroxide, (7) 5-hydroxy-2-(3-pyridyl)tetrahydrofuran (lactol, (M + H)+ = 166.06)), (8) 5-oxo-2-(3-pyridyl)tetrahydrofuran (lactone, (M + H)+ = 163.06)), (9) 4-hydroxy-4-(3-pyridyl)butanoic acid (HPBA, (M + H)+ = 182.08)), and (10) 4-hydroxy-4-(3-pyridyl)butanal ((M + H)+ = 151.06), after incubation of 2 mM NNN with enzyme sources, the NADPH regenerating system, and 5 mM Cu2+.