<?xml version="1.0" encoding="UTF-8"?>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 23:19:28 UTC</creation_date>
  <update_date>2020-04-22 15:16:37 UTC</update_date>
  <accession>BMDB0005973</accession>
  <secondary_accessions>
    <accession>BMDB05973</accession>
  </secondary_accessions>
  <name>Dimethyltryptamine</name>
  <description/>
  <synonyms>
    <synonym>2-(3-Indolyl)ethyldimethylamine</synonym>
    <synonym>3-(2-Dimethylaminoethyl)indole</synonym>
    <synonym>3-[2-(Dimethylamino)ethyl]indole</synonym>
    <synonym>DMT</synonym>
    <synonym>N,N-Dimethyl-1H-indole-3-ethylamine</synonym>
    <synonym>N,N Dimethyltryptamine</synonym>
    <synonym>(2-indol-3-Ylethyl)dimethylamine</synonym>
    <synonym>(Psychogenic)</synonym>
    <synonym>2-(1H-indol-3-yl)-N,N-Dimethylethanamine</synonym>
    <synonym>2-(1H-indol-3-yl)-N,N-Dimethylethanamine (acd/name 4.0)</synonym>
    <synonym>3-(2-(dimethylamino)Ethyl)-indole</synonym>
    <synonym>3-[2- (dimethylamino)Ethyl]-indole</synonym>
    <synonym>Dimethyltryptamine(DMT)</synonym>
    <synonym>Indolalkylamine der</synonym>
    <synonym>N,N-Dimethyl-1H-indole-3-ethanamine</synonym>
    <synonym>N,N-Dimethyl-1H-indole-3-ethanamine (9ci)</synonym>
    <synonym>N,N-Dimethyltryptamine</synonym>
    <synonym>N-(2-(1H-indol-3-yl)Ethyl)-N,N-dimethylamine (acd/name 4.0)</synonym>
    <synonym>Dimethyltryptamine</synonym>
  </synonyms>
  <chemical_formula>C12H16N2</chemical_formula>
  <average_molecular_weight>188.2688</average_molecular_weight>
  <monisotopic_moleculate_weight>188.131348522</monisotopic_moleculate_weight>
  <iupac_name>[2-(1H-indol-3-yl)ethyl]dimethylamine</iupac_name>
  <traditional_iupac>(psychogenic)</traditional_iupac>
  <cas_registry_number>61-50-7</cas_registry_number>
  <smiles>CN(C)CCC1=CNC2=CC=CC=C12</smiles>
  <inchi>InChI=1S/C12H16N2/c1-14(2)8-7-10-9-13-12-6-4-3-5-11(10)12/h3-6,9,13H,7-8H2,1-2H3</inchi>
  <inchikey>DMULVCHRPCFFGV-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tryptamines and derivatives. Tryptamines and derivatives are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Indoles and derivatives</class>
    <sub_class>Tryptamines and derivatives</sub_class>
    <direct_parent>Tryptamines and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>3-alkylindoles</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzenoids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Substituted pyrroles</alternative_parent>
      <alternative_parent>Trialkylamines</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-alkylindole</substituent>
      <substituent>Amine</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Indole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyrrole</substituent>
      <substituent>Substituted pyrrole</substituent>
      <substituent>Tertiary aliphatic amine</substituent>
      <substituent>Tertiary amine</substituent>
      <substituent>Tryptamine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>Indole alkaloids</external_descriptor>
      <external_descriptor>tryptamine alkaloid</external_descriptor>
      <external_descriptor>tryptamines</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>46 °C</value>
      <source/>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.41</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.05</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>17.16</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.55</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[2-(1H-indol-3-yl)ethyl]dimethylamine</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>188.2688</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>188.131348522</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CN(C)CCC1=CNC2=CC=CC=C12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C12H16N2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C12H16N2/c1-14(2)8-7-10-9-13-12-6-4-3-5-11(10)12/h3-6,9,13H,7-8H2,1-2H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>DMULVCHRPCFFGV-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>19.03</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>60.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>22.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</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>
    <property>
      <kind>number_of_rings</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>24516</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>27583</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99912</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>134223</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>141957</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>2324</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>2325</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>2326</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>55638</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>55639</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>55640</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>110829</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>110830</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>110831</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2665384</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2665385</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2665386</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3016719</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3016720</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3016721</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <drugbank_id>DB01488</drugbank_id>
  <foodb_id>FDB023795</foodb_id>
  <chemspider_id>5864</chemspider_id>
  <pubchem_compound_id>6089</pubchem_compound_id>
  <kegg_id>C08302</kegg_id>
  <chebi_id>28969</chebi_id>
  <knapsack_id>C00001407</knapsack_id>
  <pdbe_id/>
  <meta_cyc_id/>
  <phenol_explorer_compound_id/>
  <bigg_id/>
  <wikipedia_id>N,N-Dimethyltryptamine</wikipedia_id>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
