4-Aminoquinoline

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4-Aminoquinoline is a form of aminoquinoline with the amino group at the 4-position of the quinoline. The compound has been used as a precursor for the synthesis of its derivatives. [1]

A variety of derivatives of 4-aminoquinoline are antimalarial agents useful in treating erythrocytic plasmodial infections.[2] Examples include amodiaquine, chloroquine, and hydroxychloroquine. Other uses for the derivatives are: anti-asthmatic, antibacterial, anti-fungal, anti-malarial, antiviral and anti-inflammatory agents.[1]

A patent application for 4-aminoquinoline compounds was filed in 2002 and published in 2005.[3]

4-Aminoquinoline
 
 
Names
IUPAC name
Quinolin-4-amine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C9H8N2/c10-8-5-6-11-9-4-2-1-3-7(8)9/h1-6H,(H2,10,11)  Y
    Key: FQYRLEXKXQRZDH-UHFFFAOYSA-N  Y
  • InChI=1S/C9H8N2/c10-8-5-6-11-9-4-2-1-3-7(8)9/h1-6H,(H2,10,11)
  • n1ccc(c2ccccc12)N
Properties
C9H8N2
Molar mass 144.177 g·mol−1
Appearance Powder to crystalline, White/Yellow/Orange
Melting point 151.0 to 155.0 °C
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Causes skin and serious eye irritation
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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References

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  1. ^ a b Al-Ahmary, Khairia M.; Alenezi, Maha S.; Habeeb, Moustafa M. (2016-08-01). "Synthesis, spectroscopic and DFT theoretical studies on the hydrogen bonded charge transfer complex of 4-aminoquinoline with chloranilic acid". Journal of Molecular Liquids. 220: 166–182. doi:10.1016/j.molliq.2016.04.074. ISSN 0167-7322.
  2. ^ Bosak, Anita; Opsenica, Dejan M.; Šinko, Goran; Zlatar, Matija; Kovarik, Zrinka (2019-08-01). "Structural aspects of 4-aminoquinolines as reversible inhibitors of human acetylcholinesterase and butyrylcholinesterase". Chemico-Biological Interactions. 308: 101–109. doi:10.1016/j.cbi.2019.05.024. ISSN 0009-2797.
  3. ^ DeVita, Robert; Chang, Lehua (13 January 2005). "4-Aminoquinoline Compounds" (PDF). United States Patent Application Publication.{{cite news}}: CS1 maint: url-status (link)

Extra References

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"4-Aminoquinoline 578-68-7 | TCI America". www.tcichemicals.com. Retrieved 2020-03-06.