8-Aminoquinoline
Antimalarial drug precursor
From Wikipedia, the free encyclopedia
8-Aminoquinoline is the 8-amino derivative of quinoline. Often abbreviated AQ, it is a pale yellow solid. It is structurally analogous to 8-hydroxyquinoline.[2]
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| Names | |
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| Preferred IUPAC name
Quinolin-8-amine | |
| Identifiers | |
3D model (JSmol) |
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.008.572 |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C9H8N2 | |
| Molar mass | 144.177 g·mol−1 |
| Appearance | pale yellow solid |
| Density | 1.337 g/cm3[1] |
| Melting point | 65 °C (149 °F; 338 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Drug derivatives
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.[6][7]
Directing group
The amine functional group is amenable to formation of amides, and thus can serve as a directing group in organic synthesis.[8][9]
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.[10] AQ can also be produced by amination of 8-chloroquinoline.