Amodiaquine (CHEM022146)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:21:37 UTC
Update Date2016-11-09 01:17:26 UTC
Accession NumberCHEM022146
Identification
Common NameAmodiaquine
ClassSmall Molecule
DescriptionA 4-aminoquinoquinoline compound with anti-inflammatory properties.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
AmodiaquinaChEBI
AmodiaquinumChEBI
AmodiaquinHMDB
Amodiaquine usp24HMDB
Amodiaquine, ring-closedHMDB
CamoquinHMDB
FlavoquineHMDB
Hydrochloride, amodiaquineHMDB
Roussel brand OF amodiaquine hydrochlorideHMDB
AmodiachinHMDB
Amodiaquine hydrochlorideHMDB
CamoquineHMDB
Chemical FormulaC20H22ClN3O
Average Molecular Mass355.861 g/mol
Monoisotopic Mass355.145 g/mol
CAS Registry Number86-42-0
IUPAC Name4-[(7-chloroquinolin-4-yl)amino]-2-[(diethylamino)methyl]phenol
Traditional Nameamodiaquine
SMILESCCN(CC)CC1=C(O)C=CC(NC2=C3C=CC(Cl)=CC3=NC=C2)=C1
InChI IdentifierInChI=1S/C20H22ClN3O/c1-3-24(4-2)13-14-11-16(6-8-20(14)25)23-18-9-10-22-19-12-15(21)5-7-17(18)19/h5-12,25H,3-4,13H2,1-2H3,(H,22,23)
InChI KeyOVCDSSHSILBFBN-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 4-aminoquinolines. These are organic compounds containing an amino group attached to the 4-position of a quinoline ring system.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassAminoquinolines and derivatives
Direct Parent4-aminoquinolines
Alternative Parents
Substituents
  • Chloroquinoline
  • Haloquinoline
  • 4-aminoquinoline
  • Aminophenol
  • P-aminophenol
  • Phenylmethylamine
  • Benzylamine
  • Aniline or substituted anilines
  • Aminopyridine
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Aryl chloride
  • Monocyclic benzene moiety
  • Aryl halide
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • Tertiary amine
  • Tertiary aliphatic amine
  • Secondary amine
  • Azacycle
  • Amine
  • Organochloride
  • Organohalogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0088 g/LALOGPS
logP4.83ALOGPS
logP3.76ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)9.12ChemAxon
pKa (Strongest Basic)10.23ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area48.39 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity103.29 m³·mol⁻¹ChemAxon
Polarizability38.89 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-5039000000-deb48fd096e8eab87805Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03di-7009800000-7089f4eec8e0b64bba2cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0570-3940000000-2d4500c74767ebc68cf0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-001i-1390000000-e476bc93f0f2236bccdcSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0570-3940000000-2d4500c74767ebc68cf0Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-1390000000-e476bc93f0f2236bccdcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0039000000-62adbcf1b80da6582ca1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-1393000000-c73e48e7cfd7d390ddfaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kcs-2190000000-8de404d259f2e431ba08Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1009000000-c665029b31d3d0ae731bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-4119000000-d9ade9d08becc9d7fe95Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-9111000000-e7bdd6a9f825f1429a1eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a59-0089000000-228889052bdf8049fae3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0090000000-d45ee7ba1c5cd27865faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053r-0290000000-333fe4ea622efd6132beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0019000000-398809cbbc619aca8878Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f89-1089000000-3e1ecc2c9b62f8073845Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00lr-2290000000-6c33a84366a5268dd9ddSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00613
HMDB IDHMDB0014751
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDCQA
Wikipedia LinkAmodiaquine
Chemspider ID2080
ChEBI ID2674
PubChem Compound ID2165
Kegg Compound IDC07626
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Harrison AC, Kitteringham NR, Clarke JB, Park BK: The mechanism of bioactivation and antigen formation of amodiaquine in the rat. Biochem Pharmacol. 1992 Apr 1;43(7):1421-30.
2. Jewell H, Maggs JL, Harrison AC, O'Neill PM, Ruscoe JE, Park BK: Role of hepatic metabolism in the bioactivation and detoxication of amodiaquine. Xenobiotica. 1995 Feb;25(2):199-217.
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=11044276
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=11971651
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=17046445
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=17222819
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=18419816
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=18855526
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=19024339
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=19245687
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=26206402
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=26597254
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=26647924
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=26735991
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=26851641
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=26900802
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=26930583
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=27031231
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=8885219