<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-25 18:22:30 UTC</creation_date>
  <update_date>2026-08-18 12:08:14 UTC</update_date>
  <accession/>
  <common_name>Methoxamine</common_name>
  <class>SmallMolecule</class>
  <description>Methoxamine is an organic compound with the formula C11H17NO3 and an average molecular weight of 211.26 g/mol. Methoxamine belongs to the methoxybenzenes, a subclass of benzene and substituted derivatives within the organic compounds.

This compound is associated with six recorded sources, including healthcare, pharmaceuticals, and veterinary products specifically as cardiac stimulants excluding cardiac glycosides. It is also found in food preservation, perfumes within detergents and soaps, and electrical and electronic equipment such as television systems, electrically stimulated smoking devices, and conductors or conductive bodies characterised by the conductive materials. Recorded exposure routes for the substance include intravenous and intramuscular administration.

At the molecular level, methoxamine acts on three recorded protein targets. It functions as an agonist and binder of the Alpha-1A adrenergic receptor (ADRA1A), the Alpha-1B adrenergic receptor (ADRA1B), and the Alpha-1D adrenergic receptor (ADRA1D).</description>
  <categories/>
  <types/>
  <synonyms/>
  <chemical_formula>C11H17NO3</chemical_formula>
  <average_molecular_weight>211.2576</average_molecular_weight>
  <monisotopic_moleculate_weight>211.120843415</monisotopic_moleculate_weight>
  <iupac_name>2-amino-1-(2,5-dimethoxyphenyl)propan-1-ol</iupac_name>
  <traditional_iupac>methoxamine</traditional_iupac>
  <cas_registry_number>390-28-3</cas_registry_number>
  <smiles>COC1=CC(C(O)C(C)N)=C(OC)C=C1</smiles>
  <inchi>InChI=1S/C11H17NO3/c1-7(12)11(13)9-6-8(14-2)4-5-10(9)15-3/h4-7,11,13H,12H2,1-3H3</inchi>
  <inchikey>WJAJPNHVVFWKKL-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>1,2-aminoalcohols</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Aromatic alcohols</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Phenylpropanes</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>1,2-aminoalcohol</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Amine</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic alcohol</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Dimethoxybenzene</substituent>
      <substituent>Ether</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>P-dimethoxybenzene</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Phenylpropane</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>amphetamines</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Methoxamine Drug Metabolism</name>
      <smpdb_id>SMP0130840</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Methoxamine Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0143167</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>0.57</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.41</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.36</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>9.21e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.57</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>13.61</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-amino-1-(2,5-dimethoxyphenyl)propan-1-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>211.2576</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>211.120843415</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>COC1=CC(C(O)C(C)N)=C(OC)C=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C11H17NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C11H17NO3/c1-7(12)11(13)9-6-8(14-2)4-5-10(9)15-3/h4-7,11,13H,12H2,1-3H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WJAJPNHVVFWKKL-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>64.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>57.84</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>22.81</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</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:0x00007f7225feb688&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB00723</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>6082</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>5857</chemspider_id>
  <kegg_id/>
  <uniprot_id/>
  <omim_id/>
  <chebi_id/>
  <biocyc_id/>
  <ctd_id/>
  <stitch_id/>
  <actor_id/>
  <pdb_id/>
  <wikipidia/>
  <general_references/>
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</compound>
