8-Aminoquinoline

8-Aminoquinoline

Names
Preferred IUPAC name Quinolin-8-amine
Identifiers
CAS Number	578-66-5 Y
3D model ( JSmol )	Interactive image
ChEMBL	ChEMBL99932 Y
ChemSpider	10881 Y
ECHA InfoCard	100.008.572
PubChem CID	11359
UNII	U34EAV21TG Y
CompTox Dashboard (EPA)	DTXSID4060369
InChI InChI=1S/C9H8N2/c10-8-5-1-3-7-4-2-6-11-9(7)8/h1-6H,10H2 Y Key: WREVVZMUNPAPOV-UHFFFAOYSA-N Y
SMILES Nc1cccc2cccnc12
Properties
Chemical formula	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). Y verify (what is YN ?) Infobox references

8-Aminoquinoline is the 8-amino derivative of

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]

• 
  Primaquine
• 
  Pamaquine
• 
  Tafenoquine

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.

References