8-Aminoquinoline is the 8-amino derivative of

quinoline Quinoline is a heterocyclic aromatic organic compound with the chemical formula C9H7N. It is a colorless hygroscopic liquid with a strong odor. Aged samples, especially if exposed to light, become yellow and later brown. Quinoline is only sli ...

. Often abbreviated AQ, it is a pale yellow solid. It is structurally analogous to

8-hydroxyquinoline 8-Hydroxyquinoline (also known as oxine) is a chelate, chelating agent which has been used for the Quantitative analysis (chemistry), quantitative determination of metal ions. In aqueous solution 8-hydroxyquinoline has a pKa value of ca. 9.9 It r ...

Drug derivatives

The derivatives

primaquine Primaquine is a medication used to treat and prevent malaria and to treat ''Pneumocystis'' pneumonia. Specifically it is used for malaria due to ''Plasmodium vivax'' and '' Plasmodium ovale'' along with other medications and for prevention if oth ...

tafenoquine Tafenoquine, sold under the brand name Krintafel among others, is a medication used to prevent and to treat malaria. With respect to acute malaria, it is used together with other medications to prevent relapse by ''Plasmodium vivax''. It may be ...

and pamaquine have been tested for anti-

malaria Malaria is a mosquito-borne infectious disease that affects humans and other animals. Malaria causes symptoms that typically include fever, tiredness, vomiting, and headaches. In severe cases, it can cause jaundice, seizures, coma, or death. S ...

activity. Primaquine is still used routinely worldwide as part of the treatment of ''

Plasmodium vivax ''Plasmodium vivax'' is a protozoal parasite and a human pathogen. This parasite is the most frequent and widely distributed cause of recurring malaria. Although it is less virulent than ''Plasmodium falciparum'', the deadliest of the five huma ...

'' and ''

Plasmodium ovale ''Plasmodium ovale'' is a species of parasitic protozoon that causes tertian malaria in humans. It is one of several species of ''Plasmodium'' parasites that infect humans, including ''Plasmodium falciparum'' and ''Plasmodium vivax'' which are ...

'' malaria, although how it prevents malarial recurrences is not, at present, clear. Tafenoquine was approved for medical use in Australia and in the United States in 2018. Image:Primaquine.svg,

Primaquine Primaquine is a medication used to treat and prevent malaria and to treat ''Pneumocystis'' pneumonia. Specifically it is used for malaria due to ''Plasmodium vivax'' and '' Plasmodium ovale'' along with other medications and for prevention if oth ...

Image:Pamaquine.svg, Pamaquine Image:Tafenoquine.svg,

Tafenoquine Tafenoquine, sold under the brand name Krintafel among others, is a medication used to prevent and to treat malaria. With respect to acute malaria, it is used together with other medications to prevent relapse by ''Plasmodium vivax''. It may be ...

Directing group

The

amine In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen Hydrogen is the chemical element wi ...

functional group is amenable to formation of

amide In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a compound with the general formula , where R, R', and R″ represent organic groups or hydrogen atoms. The amide group is called a peptide bond when it i ...

s, and thus can serve as a directing group in organic synthesis.

Preparation

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. AQ can also be produced by amination of 8-chloroquinoline.

References

Abandoned drugs Antimalarial agents Quinolines {{antimicrobial-stub