<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-25 18:24:53 UTC</creation_date>
  <update_date>2026-08-19 11:51:30 UTC</update_date>
  <accession/>
  <common_name>Primaquine</common_name>
  <class>SmallMolecule</class>
  <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).</description>
  <categories/>
  <types/>
  <synonyms/>
  <chemical_formula>C15H21N3O</chemical_formula>
  <average_molecular_weight>259.3467</average_molecular_weight>
  <monisotopic_moleculate_weight>259.168462309</monisotopic_moleculate_weight>
  <iupac_name>N4-(6-methoxyquinolin-8-yl)pentane-1,4-diamine</iupac_name>
  <traditional_iupac>N4-(6-methoxyquinolin-8-yl)pentane-1,4-diamine</traditional_iupac>
  <cas_registry_number>90-34-6</cas_registry_number>
  <smiles>COC1=CC(NC(C)CCCN)=C2N=CC=CC2=C1</smiles>
  <inchi>InChI=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>
  <inchikey>INDBQLZJXZLFIT-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Quinolines and derivatives</class>
    <sub_class>Aminoquinolines and derivatives</sub_class>
    <direct_parent>Aminoquinolines and derivatives</direct_parent>
    <alternate_parents>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methoxyanilines</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyridines and derivatives</alternative_parent>
      <alternative_parent>Secondary alkylarylamines</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminoquinoline</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Ether</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Methoxyaniline</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Pyridine</substituent>
      <substituent>Secondary aliphatic/aromatic amine</substituent>
      <substituent>Secondary amine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>N-substituted diamine</descriptor>
      <descriptor>aminoquinoline</descriptor>
      <descriptor>aromatic ether</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Primaquine Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0143510</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Primaquine Predicted Metabolism Pathway</name>
      <smpdb_id>SMP0174845</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>1.64</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.76</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.66</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>5.64e-02 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.64</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>17.11</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>10.2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>N4-(6-methoxyquinolin-8-yl)pentane-1,4-diamine</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>259.3467</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>259.168462309</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>COC1=CC(NC(C)CCCN)=C2N=CC=CC2=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C15H21N3O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=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</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>INDBQLZJXZLFIT-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>60.17</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>78.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>29.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <route_of_exposure/>
  <mechanism_of_toxicity/>
  <metabolism/>
  <toxicity/>
  <lethaldose/>
  <carcinogenicity/>
  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f7279756230&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB01087</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>4908</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>4739</chemspider_id>
  <kegg_id/>
  <uniprot_id/>
  <omim_id/>
  <chebi_id/>
  <biocyc_id/>
  <ctd_id/>
  <stitch_id/>
  <actor_id/>
  <pdb_id/>
  <wikipidia/>
  <general_references/>
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  </targets>
</compound>
