A number of hydroxy analogues of the antimalarial drug primaquine [8-[(4-amino-1-methylbutyl)amino]-6-methoxyquinoline] were synthesized and characterized by 1H NMR and mass spectra. Several of the compounds were found to be active in forming methemoglobin in human erythrocytes, particularly in those from glucose-6-phosphate dehydrogenase (G6PD) deficient subjects. Decreased levels of glutathione (GSH) in G6PD-deficient erythrocytes were also found with compounds that were active methemoglobin formers.

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The duration of analgesia of the narcotics, methadone, morphine and codeine was prolonged by glucose treatment. This prolongation was associated with a decrease in in vitro metabolism of the narcotics. Chlorpromazine metabolism was not significantly inhibited by glucose treatment, indicating that glucose exerts some selectivity in the extent to which it inhibits various oxidative metabolic pathways.

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