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 |