8-Aminoquinoline

[2] The derivatives primaquine, tafenoquine and pamaquine have been tested for anti-malaria activity.

[3][4] Primaquine is still used routinely worldwide as part of the treatment of Plasmodium vivax and Plasmodium ovale malaria, although how it prevents malarial recurrences is not, at present, clear.

[5] Tafenoquine was approved for medical use in Australia and in the United States in 2018.

[8][9] The original synthesis of AQ involved nitration of quinoline to give a mixture of the 5- and 8-nitroderivatives, which were separated by distillation and sublimation.

Reduction of the 8-nitro isomer with tin powder in the presence of hydrochloric acid gave the amines.