Primaquine (CED0003322)

Record Information
Version1.0
Creation Date2016-05-25 18:24:53 UTC
Update Date2026-08-19 11:51:30 UTC
Accession NumberCHEM022232
Identification
Common NamePrimaquine
ClassSmall Molecule
Description
Primaquine is an organic compound with the formula C15H21N3O and an average molecular weight of 259.35 g/mol. Primaquine belongs to the aminoquinolines and derivatives, a subclass of quinolines and derivatives within the organic compounds. This compound is associated with ten recorded sources across various categories. In the realm of healthcare, pharmaceuticals, and veterinary products, it is used as an antiprotozoal. It is also found in food preservation within food, food processing, and cookware. Other recorded sources include household cleaning and consumer products, specifically perfumes within detergents and soaps, as well as cigar cigarettes and other smoking requisites. Additionally, it is linked to electrical and electronic equipment, including antennas, conductors or conductive bodies characterised by the conductive materials, electrodes, fixed capacitors and their manufacture, and electrically stimulated smoking devices. The recorded route of exposure for this substance is oral. At the molecular level, primaquine interacts with two recorded protein targets. It acts as an inhibitor or other unknown modulator of Ribosyldihydronicotinamide dehydrogenase [quinone] (NQO2) and Keratin, type II cytoskeletal 7 (KRT7).
Contaminant TypeNot Available
Chemical Structure
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
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-001l-7390000000-20feb8c491df9e9e6f0dNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01r6-0970000000-a3b1021cda642a6141b8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01p6-4290000000-d5f33ea098bbcd333ccfNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000l-9360000000-9f32d7ddbda48f0e2dc5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-002r-9530000000-5c70a8800c55df1915e7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-002r-9810000000-89e3b0e2b3cb4d1e9293Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00n0-5900000000-cbe196964f610f8bf1ffNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00o9-3900000000-6209d7be74ea608e7fc2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0190000000-32ab0ba382901a73b1c0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-002f-1690000000-82416f4c3f338eece150Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0920000000-65f7b4135f0db6eee15eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0900000000-17b7474db1209213f689Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-b2c7e131a6a25d115853Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01r6-0970000000-a3b1021cda642a6141b8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-2900000000-d3dfd1b72d458ffd07d7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01p6-4290000000-314f515d08e6730a1df9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000l-9360000000-3933ab4d9c2c3918ecceNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-002r-9530000000-65625d68f98ae8f36ea0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-002r-7910000000-6c3e274b81107c5e98ebNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000l-9360000000-239fc11ba8db0d498ff2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-002r-9530000000-66a8c64ae0d2826daa85Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01p6-4290000000-05e96e2502ca45a6c972Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00o9-3900000000-87c340f434edae813a48Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00n0-6900000000-8242511cd828dfb6dee0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-002r-9810000000-b0173fb2e803b0f6daa8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-002f-1690000000-82416f4c3f338eece150Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0190000000-32ab0ba382901a73b1c0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-b2c7e131a6a25d115853Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0920000000-65f7b4135f0db6eee15eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0900000000-17b7474db1209213f689Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03dl-0090000000-045cb60c1f5b86235b8dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0296-4290000000-01a4b9c14070fa4302c3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9730000000-42103ce07831ca6222a5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0090000000-1af4abbe157a64d54565Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-1290000000-d23ff1647c1e20943a1cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-006x-2930000000-c2b4d4e6f2d8325f4a71Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0090000000-86ca91c8b7fa67befcd0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0290000000-9886761b4bf6d59fabc0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00xs-8960000000-57749e90f747723b5910Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0090000000-596336a0925de2c12618Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0190000000-233a64733a67ef6d306aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-008c-1900000000-7bcf9253c32b6c16d137Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
703.0Log mg/kg[400:1300]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
385AntiprotozoalsHealthcare, pharmaceuticals & veterinary productsNot Available
506AntennasElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
Pathways
2 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Serine hydroxymethyltransferase, mitochondrial structureClick to view 3D structureSerine hydroxymethyltransferase, mitochondrialP34897HumansPredicted (SEA)0.700643
Click to view 3D structureProtein RecAP9WHJ3Mycobacterium tuberculosisPredicted (SEA)48.3444
Alpha-2A adrenergic receptor structureClick to view 3D structureAlpha-2A adrenergic receptorP08913HumansPredicted (SEA)266.244
Muscarinic acetylcholine receptor M2 structureClick to view 3D structureMuscarinic acetylcholine receptor M2P08172HumansPredicted (SEA)169.633
Muscarinic acetylcholine receptor M3 structureClick to view 3D structureMuscarinic acetylcholine receptor M3P20309HumansPredicted (SEA)129.463
Histone-lysine N-methyltransferase, H3 lysine-36 specific structureClick to view 3D structureHistone-lysine N-methyltransferase, H3 lysine-36 specificQ96L73HumansPredicted (SEA)2.10193
Muscarinic acetylcholine receptor M4 structureClick to view 3D structureMuscarinic acetylcholine receptor M4P08173HumansPredicted (SEA)155.698
Muscarinic acetylcholine receptor M1 structureClick to view 3D structureMuscarinic acetylcholine receptor M1P11229HumansPredicted (SEA)229.032
Type-1 angiotensin II receptor structureClick to view 3D structureType-1 angiotensin II receptorP30556HumansPredicted (SEA)146.279
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)168.31
Thiosulfate sulfurtransferase structureClick to view 3D structureThiosulfate sulfurtransferaseQ16762HumansPredicted (SEA)0.856341
Click to view 3D structureSigma intracellular receptor 2Q5BJF2HumansPredicted (SEA)300.342
Sigma non-opioid intracellular receptor 1 structureClick to view 3D structureSigma non-opioid intracellular receptor 1Q99720HumansPredicted (SEA)546.268
Ferroportin structureClick to view 3D structureFerroportinQ9NP59HumansPredicted (SEA)7.55137
Kappa-type opioid receptor structureClick to view 3D structureKappa-type opioid receptorP41145HumansPredicted (SEA)590.097
D(3) dopamine receptor structureClick to view 3D structureD(3) dopamine receptorP35462HumansPredicted (SEA)671.294
Alpha-2C adrenergic receptor structureClick to view 3D structureAlpha-2C adrenergic receptorP18825HumansPredicted (SEA)343.315
Vascular endothelial growth factor receptor 2 structureClick to view 3D structureVascular endothelial growth factor receptor 2P35968HumansPredicted (SEA)1736.43
Dual specificity tyrosine-phosphorylation-regulated kinase 1A structureClick to view 3D structureDual specificity tyrosine-phosphorylation-regulated kinase 1AQ13627HumansPredicted (SEA)1240.53
Alpha-2B adrenergic receptor structureClick to view 3D structureAlpha-2B adrenergic receptorP18089HumansPredicted (SEA)358.029
Aurora kinase B structureClick to view 3D structureAurora kinase BQ96GD4HumansPredicted (SEA)1473.53
Tyrosine-protein kinase SYK structureClick to view 3D structureTyrosine-protein kinase SYKP43405HumansPredicted (SEA)1101.1
Ribosyldihydronicotinamide dehydrogenase [quinone] structureClick to view 3D structureRibosyldihydronicotinamide dehydrogenase [quinone]P16083HumansPredicted (SEA)2.56902
Cytochrome P450 1A2 structureClick to view 3D structureCytochrome P450 1A2P05177HumansPredicted (SEA)86.1791
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)122.768
Concentrations
Not Available
External Links
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