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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