<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-06-03 13:48:19 UTC</creation_date>
  <update_date>2026-08-18 00:43:13 UTC</update_date>
  <accession/>
  <common_name>4-Bromo-2,5-Dimethoxyphenethylamine (2-CB)</common_name>
  <class>SmallMolecule</class>
  <description>4-Bromo-2,5-Dimethoxyphenethylamine (2-CB) belongs to the methoxybenzenes, a subclass of benzene and substituted derivatives within the organic compounds. This benzenoid compound has the chemical formula C10H14BrNO2 and an average molecular weight of 260.13 g/mol.

The compound has been identified in or released from 35 recorded sources. These include electrical and electronic equipment such as antennas, amplifiers, coils, auxiliary devices, and cores yokes or armatures, among 15 others. Within building and construction, it is found in floors, ceilings, roofs, fencing, and ladders, as well as two additional sources. In the category of food, food processing and cookware, it is associated with the processing of meats and fish, and the preparation of wine, sparkling wine, or vinegar. Additionally, it is found in household items such as watch chains and household cleaning and consumer products, specifically soap dispensers, tobacco pipes, and other smoking requisites.

Regarding its biological activity, 4-Bromo-2,5-Dimethoxyphenethylamine (2-CB) has two recorded protein targets. It acts as a partial agonist of the 5-hydroxytryptamine receptor 2C (HTR2C) and the 5-hydroxytryptamine receptor 2A (HTR2A).</description>
  <categories/>
  <types/>
  <synonyms/>
  <chemical_formula>C10H14BrNO2</chemical_formula>
  <average_molecular_weight>260.128</average_molecular_weight>
  <monisotopic_moleculate_weight>259.020791344</monisotopic_moleculate_weight>
  <iupac_name>2-(4-bromo-2,5-dimethoxyphenyl)ethan-1-amine</iupac_name>
  <traditional_iupac>bdmpea</traditional_iupac>
  <cas_registry_number>66142-81-2</cas_registry_number>
  <smiles>COC1=CC(Br)=C(OC)C=C1CCN</smiles>
  <inchi>InChI=1S/C10H14BrNO2/c1-13-9-6-8(11)10(14-2)5-7(9)3-4-12/h5-6H,3-4,12H2,1-2H3</inchi>
  <inchikey>YMHOBZXQZVXHBM-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Methoxybenzenes</sub_class>
    <direct_parent>Dimethoxybenzenes</direct_parent>
    <alternate_parents>
      <alternative_parent>2-arylethylamines</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Aryl bromides</alternative_parent>
      <alternative_parent>Bromobenzenes</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organobromides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenethylamines</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>2-arylethylamine</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Amine</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Aryl bromide</substituent>
      <substituent>Aryl halide</substituent>
      <substituent>Bromobenzene</substituent>
      <substituent>Dimethoxybenzene</substituent>
      <substituent>Ether</substituent>
      <substituent>Halobenzene</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organobromide</substituent>
      <substituent>Organohalogen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>P-dimethoxybenzene</substituent>
      <substituent>Phenethylamine</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>2-arylethylamine</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>1.84</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.99</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.12</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.99e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.84</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-(4-bromo-2,5-dimethoxyphenyl)ethan-1-amine</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>260.128</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>259.020791344</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>COC1=CC(Br)=C(OC)C=C1CCN</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C10H14BrNO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C10H14BrNO2/c1-13-9-6-8(11)10(14-2)5-7(9)3-4-12/h5-6H,3-4,12H2,1-2H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>YMHOBZXQZVXHBM-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>44.48</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>59.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>23.54</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</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/>
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  <lethaldose/>
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  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f7279244b20&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB01537</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>98527</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>88978</chemspider_id>
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</compound>
