Primaquine (CHEM022232)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:24:53 UTC
Update Date2016-11-09 01:17:27 UTC
Accession NumberCHEM022232
Identification
Common NamePrimaquine
ClassSmall Molecule
DescriptionAn N-substituted diamine that is pentane-1,4-diamine substituted by a 6-methoxyquinolin-8-yl group at the N(4) position. It is a drug used in the treatment of malaria and Pneumocystis pneumonia.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
6-Methoxy-8-(4-amino-1-methylbutylamino)quinolineChEBI
8-((4-Amino-1-methylbutyl)amino)-6-methoxyquinolineChEBI
8-(4-Amino-1-methylbutylamino)-6-methoxyquinolineChEBI
Neo-quipenylChEBI
PrimachinChEBI
PrimachinumChEBI
PrimaquinChEBI
PrimaquinaChEBI
PrimaquinumChEBI
KanaprimKegg
Diphosphate, primaquineMeSH
Phosphate, primaquineMeSH
PrimacinMeSH
Primaquine diphosphateMeSH
Primaquine phosphateMeSH
Boucher and muir brand OF primaquine phosphateMeSH, HMDB
Chemical FormulaC15H21N3O
Average Molecular Mass259.347 g/mol
Monoisotopic Mass259.168 g/mol
CAS Registry Number90-34-6
IUPAC NameN4-(6-methoxyquinolin-8-yl)pentane-1,4-diamine
Traditional NameN4-(6-methoxyquinolin-8-yl)pentane-1,4-diamine
SMILESCOC1=CC(NC(C)CCCN)=C2N=CC=CC2=C1
InChI IdentifierInChI=1S/C15H21N3O/c1-11(5-3-7-16)18-14-10-13(19-2)9-12-6-4-8-17-15(12)14/h4,6,8-11,18H,3,5,7,16H2,1-2H3
InChI KeyINDBQLZJXZLFIT-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aminoquinolines and derivatives. These are organic compounds containing an amino group attached to a quinoline ring system.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassAminoquinolines and derivatives
Direct ParentAminoquinolines and derivatives
Alternative Parents
Substituents
  • Aminoquinoline
  • Methoxyaniline
  • Anisole
  • Alkyl aryl ether
  • Secondary aliphatic/aromatic amine
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • Ether
  • Azacycle
  • Secondary amine
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Amine
  • Organic oxygen 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 Solubility0.056 g/LALOGPS
logP2.76ALOGPS
logP1.64ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)17.11ChemAxon
pKa (Strongest Basic)10.2ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area60.17 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity78.51 m³·mol⁻¹ChemAxon
Polarizability29.92 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001l-7390000000-20feb8c491df9e9e6f0dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-01r6-0970000000-a3b1021cda642a6141b8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-01p6-4290000000-d5f33ea098bbcd333ccfSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000l-9360000000-9f32d7ddbda48f0e2dc5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-002r-9530000000-5c70a8800c55df1915e7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-002r-9810000000-89e3b0e2b3cb4d1e9293Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00n0-5900000000-cbe196964f610f8bf1ffSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00o9-3900000000-6209d7be74ea608e7fc2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0190000000-32ab0ba382901a73b1c0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-002f-1690000000-82416f4c3f338eece150Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0920000000-65f7b4135f0db6eee15eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0900000000-17b7474db1209213f689Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0900000000-b2c7e131a6a25d115853Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-01r6-0970000000-a3b1021cda642a6141b8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-001i-2900000000-d3dfd1b72d458ffd07d7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-01p6-4290000000-314f515d08e6730a1df9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000l-9360000000-3933ab4d9c2c3918ecceSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-002r-9530000000-65625d68f98ae8f36ea0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-002r-7910000000-6c3e274b81107c5e98ebSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-000l-9360000000-239fc11ba8db0d498ff2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0090000000-045cb60c1f5b86235b8dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0296-4290000000-01a4b9c14070fa4302c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9730000000-42103ce07831ca6222a5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-1af4abbe157a64d54565Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1290000000-d23ff1647c1e20943a1cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-2930000000-c2b4d4e6f2d8325f4a71Spectrum
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 IDDB01087
HMDB IDHMDB0250792
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPrimaquine
Chemspider ID4739
ChEBI ID8405
PubChem Compound ID4908
Kegg Compound IDC07627
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10928454
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11303037
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=12036132
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=14917959
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=15494911
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=16537060
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=17253504
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=18930565
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=19114311
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=2210868
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=28279180
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=28289025
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=8920977