U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C9H8N2
Molecular Weight 144.1732
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 4-AMINOQUINOLINE

SMILES

NC1=C2C=CC=CC2=NC=C1

InChI

InChIKey=FQYRLEXKXQRZDH-UHFFFAOYSA-N
InChI=1S/C9H8N2/c10-8-5-6-11-9-4-2-1-3-7(8)9/h1-6H,(H2,10,11)

HIDE SMILES / InChI

Approval Year

PubMed

PubMed

TitleDatePubMed
Continued cytoadherence of Plasmodium falciparum infected red blood cells after antimalarial treatment.
2010-02
Antimalarial activities of ferroquine conjugates with either glutathione reductase inhibitors or glutathione depletors via a hydrolyzable amide linker.
2009-12-01
Genetic basis of inherited macular dystrophies and implications for stem cell therapy.
2009-11
Synthesis and antimalarial activity of new chloroquine analogues carrying a multifunctional linear side chain.
2009-09-15
Synthesis of oxalamide and triazine derivatives as a novel class of hybrid 4-aminoquinoline with potent antiplasmodial activity.
2009-09-01
9-Aminoacridine inhibition of HIV-1 Tat dependent transcription.
2009-07-24
Interference with hemozoin formation represents an important mechanism of schistosomicidal action of antimalarial quinoline methanols.
2009-07-14
A comparative, randomized clinical trial of artemisinin/naphtoquine twice daily one day versus artemether/lumefantrine six doses regimen in children and adults with uncomplicated falciparum malaria in Côte d'Ivoire.
2009-07-03
Plasmodium berghei ANKA: selection of resistance to piperaquine and lumefantrine in a mouse model.
2009-07
In vivo and in vitro efficacy of amodiaquine against Plasmodium falciparum in an area of continued use of 4-aminoquinolines in East Africa.
2009-06-01
Synthesis of novel thiourea, thiazolidinedione and thioparabanic acid derivatives of 4-aminoquinoline as potent antimalarials.
2009-05-01
Replacement of the 4'-hydroxy group of amodiaquine and amopyroquine by aromatic and aliphatic substituents: synthesis and antimalarial activity.
2009-04
Field-adapted sampling of whole blood to determine the levels of amodiaquine and its metabolite in children with uncomplicated malaria treated with amodiaquine plus artesunate combination.
2009-03-30
Candidate selection and preclinical evaluation of N-tert-butyl isoquine (GSK369796), an affordable and effective 4-aminoquinoline antimalarial for the 21st century.
2009-03-12
Combining 4-aminoquinoline- and clotrimazole-based pharmacophores toward innovative and potent hybrid antimalarials.
2009-01-22
Comparative preclinical drug metabolism and pharmacokinetic evaluation of novel 4-aminoquinoline anti-malarials.
2009-01
Synthesis and bioevaluation of hybrid 4-aminoquinoline triazines as a new class of antimalarial agents.
2008-12-15
Antiplasmodial, beta-haematin inhibition, antitrypanosomal and cytotoxic activity in vitro of novel 4-aminoquinoline 2-imidazolines.
2008-12-07
Ferroquine, an ingenious antimalarial drug: thoughts on the mechanism of action.
2008-11-20
New chimeric antimalarials with 4-aminoquinoline moiety linked to a tetraoxane skeleton.
2008-10-09
Chronic urotensin II infusion enhances macrophage foam cell formation and atherosclerosis in apolipoprotein E-knockout mice.
2008-10
Synthesis and antimalarial activity of novel side chain modified antimalarial agents derived from 4-aminoquinoline.
2008-09
Synthesis and antimalarial activity of new amino analogues of amodiaquine.
2008-09
Design, synthesis and in vitro antitumor activity of 4-aminoquinoline and 4-aminoquinazoline derivatives targeting EGFR tyrosine kinase.
2008-08-15
Molecular epidemiology of drug-resistant malaria in western Kenya highlands.
2008-07-31
Antimalarial activity of novel pyrrolizidinyl derivatives of 4-aminoquinoline.
2008-07-01
Recovery of mouse neuromuscular junctions from single and repeated injections of botulinum neurotoxin A.
2008-07-01
Heterogeneous distribution of Plasmodium falciparum drug resistance haplotypes in subsets of the host population.
2008-05-06
The usefulness of twenty-four molecular markers in predicting treatment outcome with combination therapy of amodiaquine plus sulphadoxine-pyrimethamine against falciparum malaria in Papua New Guinea.
2008-04-19
Antimalarial dual drugs based on potent inhibitors of glutathione reductase from Plasmodium falciparum.
2008-03-13
Sulfadoxine-pyrimethamine-based combinations for malaria: a randomised blinded trial to compare efficacy, safety and selection of resistance in Malawi.
2008-02-13
Synthesis and in vitro cytotoxicity evaluation of 4-aminoquinoline derivatives.
2008-02
[Urotensin II promotes atherosclerosis].
2008-01
Pharmacodynamic interaction between 4-aminoquinolines and retinol in Plasmodium falciparum in vitro.
2008
Bis-quinolinium cyclophanes: highly potent and selective non-peptidic blockers of the apamin-sensitive Ca2+-activated K+ channel.
2008
Metallocene antimalarials: the continuing quest.
2008
Simultaneous determination of amodiaquine and its active metabolite in human blood by ion-pair liquid chromatography-tandem mass spectrometry.
2007-12-01
Chloroquine ototoxicity.
2007-11
In vitro activity of ferroquine (SSR 97193) against Plasmodium falciparum isolates from the Thai-Burmese border.
2007-06-27
Activity of piperaquine and other 4-aminoquinoline antiplasmodial drugs against chloroquine-sensitive and resistant blood-stages of Plasmodium falciparum. Role of beta-haematin inhibition and drug concentration in vacuolar water- and lipid-phases.
2007-06-15
Different pH requirements are associated with divergent inhibitory effects of chloroquine on human and avian influenza A viruses.
2007-05-03
Response to malaria epidemics in Africa.
2007-05
Plasmodium falciparum Na+/H+ exchanger activity and quinine resistance.
2007-05
Exploration of rate-limiting conformational state for 5-[(7-chloro-4-quinolinyl)amino]-3-[(alkylamino)methyl][1,1'-biphenyl]-2-ols and N(omega)-oxides (tebuquine analogues) for antimalarial activity using molecular shape analysis and molecular field analysis studies.
2007-04-12
Synthesis and antimalarial activity of new isotebuquine analogues.
2007-02-22
Intermittent preventive treatment for malaria in pregnancy in Africa: what's new, what's needed?
2007-02-16
Synthesis and antimalarial activity of side chain modified 4-aminoquinoline derivatives.
2007-01-25
Fujita-Ban QSAR analysis and CoMFA study of quinoline antagonists of immunostimulatory CpG-oligodeoxynucleotides.
2007-01-01
[Ocular toxicity due to 4-aminoquinoline derivatives].
2006-11-08
The use of antirheumatic disease drugs during pregnancy.
2006-11
Patents
Name Type Language
4-AMINOQUINOLINE
VANDF  
Systematic Name English
4-AMINOQUINOLINE [VANDF]
Preferred Name English
QUINOLINE, 4-AMINO-
Systematic Name English
4-QUINOLYLAMINE
Systematic Name English
4-QUINOLINAMINE
Systematic Name English
Code System Code Type Description
FDA UNII
GTE5P5L97N
Created by admin on Mon Mar 31 18:41:28 GMT 2025 , Edited by admin on Mon Mar 31 18:41:28 GMT 2025
PRIMARY
MESH
C001920
Created by admin on Mon Mar 31 18:41:28 GMT 2025 , Edited by admin on Mon Mar 31 18:41:28 GMT 2025
PRIMARY
CAS
578-68-7
Created by admin on Mon Mar 31 18:41:28 GMT 2025 , Edited by admin on Mon Mar 31 18:41:28 GMT 2025
PRIMARY
PUBCHEM
68476
Created by admin on Mon Mar 31 18:41:28 GMT 2025 , Edited by admin on Mon Mar 31 18:41:28 GMT 2025
PRIMARY
EPA CompTox
DTXSID70206491
Created by admin on Mon Mar 31 18:41:28 GMT 2025 , Edited by admin on Mon Mar 31 18:41:28 GMT 2025
PRIMARY
WIKIPEDIA
4-AMINOQUINOLINE
Created by admin on Mon Mar 31 18:41:28 GMT 2025 , Edited by admin on Mon Mar 31 18:41:28 GMT 2025
PRIMARY