<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-06-03 11:14:14 UTC</creation_date>
  <update_date>2026-08-18 11:18:40 UTC</update_date>
  <accession/>
  <common_name>3,4-methylenedioxymethamphetamine</common_name>
  <class>SmallMolecule</class>
  <description>3,4-methylenedioxymethamphetamine is an organic compound with the formula C11H15NO2 and an average molecular weight of 193.24 g/mol. 3,4-methylenedioxymethamphetamine belongs to the benzodioxoles, a class of organoheterocyclic compounds within the organic compounds.

The compound is found in or released from 38 recorded sources. These include household cleaning and consumer products such as soap detergents, bleaching agents, tobacco smoke filters, cigar cigarettes, and non electric simulated devices for simulated smoking. It is also associated with food, food processing and cookware, specifically processing meats, food preservation, and fermentation processes for beer. Other sources include drinking water and water supply, as well as building and construction materials such as floors, ceilings, roofs, fencing, and stairs and ramps. Additionally, it is found in electrical and electronic equipment, including antennas, amplifiers, communication cables or conductors, auxiliary devices, and conductors or conductive bodies characterised by the conductive materials, among 19 other sources. The recorded exposure route for this compound is oral.

At the molecular level, 3,4-methylenedioxymethamphetamine interacts with seven recorded protein targets. It acts as an agonist, inhibitor, or negative modulator of the sodium-dependent serotonin transporter (SLC6A4), the sodium-dependent dopamine transporter (SLC6A3), the synaptic vesicular amine transporter (SLC18A2), and the 5-hydroxytryptamine receptor 2A (HTR2A), as well as three other proteins. Regarding health effects, the compound is associated with depression (PMC5996082) and dizziness (PMC5996082).</description>
  <categories/>
  <types>
    <type>Human Neurotoxin</type>
  </types>
  <synonyms/>
  <chemical_formula>C11H15NO2</chemical_formula>
  <average_molecular_weight>193.2423</average_molecular_weight>
  <monisotopic_moleculate_weight>193.110278729</monisotopic_moleculate_weight>
  <iupac_name>[1-(2H-1,3-benzodioxol-5-yl)propan-2-yl](methyl)amine</iupac_name>
  <traditional_iupac>MDMA</traditional_iupac>
  <cas_registry_number>42542-10-9</cas_registry_number>
  <smiles>CNC(C)CC1=CC2=C(OCO2)C=C1</smiles>
  <inchi>InChI=1S/C11H15NO2/c1-8(12-2)5-9-3-4-10-11(6-9)14-7-13-10/h3-4,6,8,12H,5,7H2,1-2H3</inchi>
  <inchikey>SHXWCVYOXRDMCX-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Benzodioxoles</class>
    <sub_class/>
    <direct_parent>Benzodioxoles</direct_parent>
    <alternate_parents>
      <alternative_parent>Acetals</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Benzenoids</alternative_parent>
      <alternative_parent>Dialkylamines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Oxacyclic compounds</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Acetal</substituent>
      <substituent>Amine</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Benzodioxole</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Oxacycle</substituent>
      <substituent>Secondary aliphatic amine</substituent>
      <substituent>Secondary amine</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>amphetamines</descriptor>
      <descriptor>benzodioxoles</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways/>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>1.86</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.65</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.78</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>3.22e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>10.14</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>[1-(2H-1,3-benzodioxol-5-yl)propan-2-yl](methyl)amine</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>193.2423</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>193.110278729</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CNC(C)CC1=CC2=C(OCO2)C=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C11H15NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C11H15NO2/c1-8(12-2)5-9-3-4-10-11(6-9)14-7-13-10/h3-4,6,8,12H,5,7H2,1-2H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SHXWCVYOXRDMCX-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>30.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>54.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>21.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</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>
  </predicted_properties>
  <route_of_exposure/>
  <mechanism_of_toxicity/>
  <metabolism/>
  <toxicity/>
  <lethaldose/>
  <carcinogenicity/>
  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f72271c9300&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB01454</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>1615</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>1556</chemspider_id>
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  <wikipidia/>
  <general_references/>
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</compound>
