<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2011-09-21 00:18:15 UTC</creation_date>
  <update_date>2015-10-09 22:30:54 UTC</update_date>
  <accession>FDB022706</accession>
  <name>Imipramine</name>
  <description>The prototypical tricyclic antidepressant. It has been used in major depression, dysthymia, bipolar depression, attention deficit disorders, agoraphobia, and panic disorders. It has less sedative effect than some other members of this therapeutic group. -- Pubchem; Imipramine (sold as Antideprin, Janimine, Tofranil) is an antidepressant medication, a tricyclic antidepressant of the dibenzazepine group, mainly used in the treatment of clinical depression and enuresis. -- Wikipedia [HMDB]</description>
  <synonyms>
    <synonym>10,11-dihydro-N,N-Dimethyl-5H-dibenz[b,F]azepine-5-propanamine</synonym>
    <synonym>3-(5H-DIBENZO[b,F]azepin-5-yl)-N,N-dimethylpropan-1-amine</synonym>
    <synonym>5-[3-(dimethylamino)Propyl]-10,11-dihydro-5H-dibenz[b,F]azepine</synonym>
    <synonym>Antideprin</synonym>
    <synonym>Berkomine</synonym>
    <synonym>Chimoreptin</synonym>
    <synonym>Declomipramine</synonym>
    <synonym>Dimipressin</synonym>
    <synonym>DPID</synonym>
    <synonym>Dyna-Zina</synonym>
    <synonym>Dynaprin</synonym>
    <synonym>Eupramin</synonym>
    <synonym>Feinalmin</synonym>
    <synonym>Imavate</synonym>
    <synonym>Imidobenzyle</synonym>
    <synonym>Imilanyle</synonym>
    <synonym>Imipramin</synonym>
    <synonym>Imipramine</synonym>
    <synonym>Imipraminum</synonym>
    <synonym>Imizine</synonym>
    <synonym>Irmin</synonym>
    <synonym>Janimine</synonym>
    <synonym>Lofepramine</synonym>
    <synonym>Melipramin</synonym>
    <synonym>Melipramine</synonym>
    <synonym>N-(g-Dimethylaminopropyl)iminodibenzyl</synonym>
    <synonym>N-(gamma-Dimethylaminopropyl)iminodibenzyl</synonym>
    <synonym>N-(γ-dimethylaminopropyl)iminodibenzyl</synonym>
    <synonym>Psychoforin</synonym>
    <synonym>Surmontil</synonym>
    <synonym>Surplix</synonym>
    <synonym>Teperine</synonym>
    <synonym>Timolet</synonym>
    <synonym>Tofranil</synonym>
    <synonym>Tofranil base</synonym>
    <synonym>Tofranil-Pm</synonym>
    <synonym>Trimipramine Maleate</synonym>
  </synonyms>
  <chemical_formula>C19H24N2</chemical_formula>
  <average_molecular_weight>280.4073</average_molecular_weight>
  <monisotopic_moleculate_weight>280.193948778</monisotopic_moleculate_weight>
  <iupac_name>(3-{2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-2-yl}propyl)dimethylamine</iupac_name>
  <traditional_iupac>(3-{2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-2-yl}propyl)dimethylamine</traditional_iupac>
  <cas_registry_number>50-49-7</cas_registry_number>
  <smiles>CN(C)CCCN1C2=CC=CC=C2CCC2=CC=CC=C12</smiles>
  <inchi>InChI=1S/C19H24N2/c1-20(2)14-7-15-21-18-10-5-3-8-16(18)12-13-17-9-4-6-11-19(17)21/h3-6,8-11H,7,12-15H2,1-2H3</inchi>
  <inchikey>BCGWQEUPMDMJNV-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as dibenzazepines. Dibenzazepines are compounds with two benzene rings connected by an azepine ring. Azepine is an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom.</description>
    <direct_parent>Dibenzazepines</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Benzazepines</class>
    <sub_class>Dibenzazepines</sub_class>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Alkyldiarylamines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Azepines</alternative_parent>
      <alternative_parent>Benzenoids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Trialkylamines</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alkyldiarylamine</substituent>
      <substituent>Amine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Azepine</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Dibenzazepine</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Tertiary aliphatic amine</substituent>
      <substituent>Tertiary aliphatic/aromatic amine</substituent>
      <substituent>Tertiary amine</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>a small molecule</external_descriptor>
      <external_descriptor>dibenzoazepine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.53</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.63</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>6.64e-02 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>4.28</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>9.2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>(3-{2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-2-yl}propyl)dimethylamine</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>280.4073</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>280.193948778</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CN(C)CCCN1C2=CC=CC=C2CCC2=CC=CC=C12</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C19H24N2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C19H24N2/c1-20(2)14-7-15-21-18-10-5-3-8-16(18)12-13-17-9-4-6-11-19(17)21/h3-6,8-11H,7,12-15H2,1-2H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>BCGWQEUPMDMJNV-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>6.48</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>90.61</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>33.39</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>0</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>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>177</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1752</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1692</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>6635</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27631</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99707</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>132486</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>140220</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1705</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1706</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1707</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5465</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>248832</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>248833</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>248834</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>268773</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>268774</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>268775</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441054</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2242305</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2242854</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2243544</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2244427</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2245666</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2246529</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2247768</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2248629</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2249090</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2249308</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2249737</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2250694</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2251720</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2352976</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB01848</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>5881</chebi_id>
  <biocyc_id/>
  <het_id>IXX</het_id>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
  </general_references>
  <foods>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
    <enzyme>
      <name>Adenosine receptor A1</name>
      <uniprot_id>P30542</uniprot_id>
      <uniprot_name/>
      <gene_name>ADORA1</gene_name>
    </enzyme>
    <enzyme>
      <name>UDP-glucuronosyltransferase 1-4</name>
      <uniprot_id>P22310</uniprot_id>
      <uniprot_name/>
      <gene_name>UGT1A4</gene_name>
    </enzyme>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
