<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2011-09-21 00:18:17 UTC</creation_date>
  <update_date>2015-10-09 22:30:55 UTC</update_date>
  <accession>FDB022708</accession>
  <name>Verapamil</name>
  <description>A calcium channel blocker that is a class IV anti-arrhythmia agent. -- Pubchem; 
Calcium channel antagonists can be quite toxic. In the management of poisoning, early recognition is critical. Calcium channel antagonists are frequently prescribed, and the potential for serious morbidity and mortality with over dosage is significant. Ingestion of these agents should be suspected in any patient who presents in an overdose situation with unexplained hypotension and conduction abnormalities. The potential for toxicity should be noted in patients with underlying hepatic or renal dysfunction who are receiving therapeutic doses. (PMID 8213877) [HMDB]</description>
  <synonyms>
    <synonym>Akilen</synonym>
    <synonym>Anpec</synonym>
    <synonym>Apo-Verap</synonym>
    <synonym>Arpamyl LP</synonym>
    <synonym>Berkatens</synonym>
    <synonym>Calan</synonym>
    <synonym>Calan SR</synonym>
    <synonym>Calaptin</synonym>
    <synonym>Calaptin 240 SR</synonym>
    <synonym>Calcan</synonym>
    <synonym>Cardiabeltin</synonym>
    <synonym>Cardiagutt</synonym>
    <synonym>Cardibeltin</synonym>
    <synonym>Cardioprotect</synonym>
    <synonym>Caveril</synonym>
    <synonym>Civicor</synonym>
    <synonym>Civicor Retard</synonym>
    <synonym>Coraver</synonym>
    <synonym>Cordilox</synonym>
    <synonym>Cordilox SR</synonym>
    <synonym>Corpamil</synonym>
    <synonym>Covera-Hs</synonym>
    <synonym>D-365</synonym>
    <synonym>delta-365</synonym>
    <synonym>Dignover</synonym>
    <synonym>Dilacoran</synonym>
    <synonym>Dilacoran HTA</synonym>
    <synonym>Durasoptin</synonym>
    <synonym>Elthon</synonym>
    <synonym>Falicard</synonym>
    <synonym>Finoptin</synonym>
    <synonym>Flamon</synonym>
    <synonym>Geangin</synonym>
    <synonym>Harteze</synonym>
    <synonym>Hexasoptin</synonym>
    <synonym>Hexasoptin Retard</synonym>
    <synonym>Hormitol</synonym>
    <synonym>Ikacor</synonym>
    <synonym>Ikapress</synonym>
    <synonym>Inselon</synonym>
    <synonym>Iproveratril</synonym>
    <synonym>Isoptin</synonym>
    <synonym>Isoptin Retard</synonym>
    <synonym>Isoptin SR</synonym>
    <synonym>Isoptine</synonym>
    <synonym>Isoptino</synonym>
    <synonym>Isotopin</synonym>
    <synonym>Izoptin</synonym>
    <synonym>Jenapamil</synonym>
    <synonym>Lekoptin</synonym>
    <synonym>Lodixal</synonym>
    <synonym>Magotiron</synonym>
    <synonym>Manidon</synonym>
    <synonym>Manidon Retard</synonym>
    <synonym>Novapamyl LP</synonym>
    <synonym>Novo-Veramil</synonym>
    <synonym>Nu-Verap</synonym>
    <synonym>Ormil</synonym>
    <synonym>Praecicor</synonym>
    <synonym>Quasar</synonym>
    <synonym>Rapam</synonym>
    <synonym>Robatelan</synonym>
    <synonym>Securon</synonym>
    <synonym>Tarka</synonym>
    <synonym>Univer</synonym>
    <synonym>Univex</synonym>
    <synonym>Vasolan</synonym>
    <synonym>Vasomil</synonym>
    <synonym>Vasopten</synonym>
    <synonym>Vera-Sanorania</synonym>
    <synonym>Verabeta</synonym>
    <synonym>Veracaps SR</synonym>
    <synonym>Veracor</synonym>
    <synonym>Verahexal</synonym>
    <synonym>Veraloc</synonym>
    <synonym>Veramex</synonym>
    <synonym>Veramil</synonym>
    <synonym>Verapamil</synonym>
    <synonym>Verapamil Acis</synonym>
    <synonym>Verapamil AL</synonym>
    <synonym>Verapamil Atid</synonym>
    <synonym>Verapamil Basics</synonym>
    <synonym>Verapamil Ebewe</synonym>
    <synonym>Verapamil hcl</synonym>
    <synonym>Verapamil Henning</synonym>
    <synonym>Verapamil Injection</synonym>
    <synonym>Verapamil MSD</synonym>
    <synonym>Verapamil NM</synonym>
    <synonym>Verapamil NM Pharma</synonym>
    <synonym>Verapamil Nordic</synonym>
    <synonym>Verapamil PB</synonym>
    <synonym>Verapamil Riker</synonym>
    <synonym>Verapamil SR</synonym>
    <synonym>Verapamil Verla</synonym>
    <synonym>Verapamil-AbZ</synonym>
    <synonym>Verapamilo</synonym>
    <synonym>Verapamilum</synonym>
    <synonym>Verapin</synonym>
    <synonym>Verapress 240 SR</synonym>
    <synonym>Verasal</synonym>
    <synonym>Verasifar</synonym>
    <synonym>Veratensin</synonym>
    <synonym>Verdilac</synonym>
    <synonym>Verelan</synonym>
    <synonym>Verelan PM</synonym>
    <synonym>Verelan SR</synonym>
    <synonym>Veroptinstada</synonym>
    <synonym>Verpamil</synonym>
    <synonym>Vetrimil</synonym>
    <synonym>Vortac</synonym>
  </synonyms>
  <chemical_formula>C27H38N2O4</chemical_formula>
  <average_molecular_weight>454.6016</average_molecular_weight>
  <monisotopic_moleculate_weight>454.283157714</monisotopic_moleculate_weight>
  <iupac_name>2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile</iupac_name>
  <traditional_iupac>veraβ</traditional_iupac>
  <cas_registry_number>52-53-9</cas_registry_number>
  <smiles>COC1=C(OC)C=C(CCN(C)CCCC(C#N)(C(C)C)C2=CC(OC)=C(OC)C=C2)C=C1</smiles>
  <inchi>InChI=1S/C27H38N2O4/c1-20(2)27(19-28,22-10-12-24(31-5)26(18-22)33-7)14-8-15-29(3)16-13-21-9-11-23(30-4)25(17-21)32-6/h9-12,17-18,20H,8,13-16H2,1-7H3</inchi>
  <inchikey>SGTNSNPWRIOYBX-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phenylbutylamines. Phenylbutylamines are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine.</description>
    <direct_parent>Phenylbutylamines</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Phenylbutylamines</sub_class>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Dimethoxybenzenes</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Nitriles</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenethylamines</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Phenylpropanes</alternative_parent>
      <alternative_parent>Trialkylamines</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Amine</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Carbonitrile</substituent>
      <substituent>Dimethoxybenzene</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Methoxybenzene</substituent>
      <substituent>Nitrile</substituent>
      <substituent>O-dimethoxybenzene</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenethylamine</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Phenylbutylamine</substituent>
      <substituent>Phenylpropane</substituent>
      <substituent>Tertiary aliphatic amine</substituent>
      <substituent>Tertiary amine</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>aromatic ether</external_descriptor>
      <external_descriptor>nitrile</external_descriptor>
      <external_descriptor>polyether</external_descriptor>
      <external_descriptor>tertiary amino compound</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>5.23</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.06</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>3.94e-03 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>5.04</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>9.68</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>454.6016</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>454.283157714</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>COC1=C(OC)C=C(CCN(C)CCCC(C#N)(C(C)C)C2=CC(OC)=C(OC)C=C2)C=C1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C27H38N2O4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C27H38N2O4/c1-20(2)27(19-28,22-10-12-24(31-5)26(18-22)33-7)14-8-15-29(3)16-13-21-9-11-23(30-4)25(17-21)32-6/h9-12,17-18,20H,8,13-16H2,1-7H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>SGTNSNPWRIOYBX-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>63.95</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>132.65</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>51.7</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>13</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>6</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::NmrTwoD</type>
      <spectrum_id>1694</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25919</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>122410</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>126312</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>133613</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>141347</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>640</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1754</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1711</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1712</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1713</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5476</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5477</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5478</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5479</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5480</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5481</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5482</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5483</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5484</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5485</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>264744</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>264745</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>264746</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>284673</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>284674</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>284675</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441374</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441375</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441376</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441377</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441378</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>442323</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB01850</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce33334710&gt;</reference>
    <reference>#&lt;Reference:0x000055ce33334558&gt;</reference>
    <reference>#&lt;Reference:0x000055ce333343a0&gt;</reference>
    <reference>#&lt;Reference:0x000055ce333341e8&gt;</reference>
    <reference>#&lt;Reference:0x000055ce33334030&gt;</reference>
    <reference>#&lt;Reference:0x000055ce33333e28&gt;</reference>
    <reference>#&lt;Reference:0x000055ce33333c70&gt;</reference>
    <reference>#&lt;Reference:0x000055ce33333ab8&gt;</reference>
    <reference>#&lt;Reference:0x000055ce33333900&gt;</reference>
    <reference>#&lt;Reference:0x000055ce33333748&gt;</reference>
    <reference>#&lt;Reference:0x000055ce33333590&gt;</reference>
    <reference>#&lt;Reference:0x000055ce333333d8&gt;</reference>
    <reference>#&lt;Reference:0x000055ce33333220&gt;</reference>
    <reference>#&lt;Reference:0x000055ce33333068&gt;</reference>
    <reference>#&lt;Reference:0x000055ce33332eb0&gt;</reference>
    <reference>#&lt;Reference:0x000055ce33332cf8&gt;</reference>
    <reference>#&lt;Reference:0x000055ce33332b40&gt;</reference>
    <reference>#&lt;Reference:0x000055ce33332988&gt;</reference>
    <reference>#&lt;Reference:0x000055ce333327a8&gt;</reference>
    <reference>#&lt;Reference:0x000055ce333325f0&gt;</reference>
    <reference>#&lt;Reference:0x000055ce33332438&gt;</reference>
    <reference>#&lt;Reference:0x000055ce33332280&gt;</reference>
  </general_references>
  <foods>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
