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Table 1 Identified metabolites from CYP2D6-mediated metabolism of primaquine and its enantiomers

From: Enantioselective metabolism of primaquine by human CYP2D6

Peak [M+H]+ RT Formula Remarks
260.13 1.5 C14H17N3O2 Oxidized product of 5-OH-PQ, preferentially generated from the (+)-primaquine (twice as much compared to (−)-primaquine)
261.16 8.7 C15H20N2O2 Oxidative deamination of primaquine and subsequent reduction to primaquine alcohol.
275.14 8.8 C15H18N2O3 Possibly terminal amine oxidation, with oxidation and quinone-imine formation on quinoline ring, predominantly formed from (−)-primaquine (2:1)
276.17 2.08 C15H21N3O2 Identified as 4-OH-PQ; Formed 5 times more predominantly with (−)-primaquine than (+)-primaquine
276.17 3.64 C15H21N3O2 Identified as 2-OH-PQ; Generated in the ratio 4:1 by (+)-primaquine vs (−)-primaquine
276.17 4.78 C15H21N3O2 Identified as 3-OH-PQ; Generated in the ratio 2:3 by (+)-primaquine and (−)-primaquine
290.15 3.42 C15H20N3O3 Putatively identified as dihydroxylated primaquine metabolite converted to quinone-imines, generated in the ratio 3:2 by (−)-primaquine and (+)-primaquine.
290.15 4.56 C15H20N3O3 Putatively identified as a dihydroxylated primaquine metabolite converted to quinone-imine; Generated more predominantly with (−)-primaquine, minimally with (±)-primaquine and not detected with (+)-primaquine
292.16 4.59 C15H21N3O3 Putatively identified as dihydroxyprimaquine; Generated with (−)-primaquine only
306.14 3.65 C15H20N3O4 Putatively identified as trihydroxylated primaquine converted to the quinone-imine; selectively generated with (+)-primaquine
308.16 1.4 C15H21N3O4 Putatively identified as trihydroxyprimaquine; detected in trace amount; more prominently generated with (+)-primaquine