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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).
|
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]
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]
The amine functional group is amenable to formation of amides, and thus can serve as a directing group in organic synthesis. [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. [10] AQ can also be produced by amination of 8-chloroquinoline.
![]() | |
Names | |
---|---|
Preferred IUPAC name
Quinolin-8-amine | |
Identifiers | |
3D model (
JSmol)
|
|
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.008.572 |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
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).
|
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]
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]
The amine functional group is amenable to formation of amides, and thus can serve as a directing group in organic synthesis. [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. [10] AQ can also be produced by amination of 8-chloroquinoline.