<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 03:43:38 UTC</creation_date>
  <update_date>2026-08-19 12:46:38 UTC</update_date>
  <accession/>
  <common_name>Metoprolol</common_name>
  <class>SmallMolecule</class>
  <description>Metoprolol is an organic compound with the formula C15H25NO3 and an average molecular weight of 267.36 g/mol. Metoprolol belongs to the tyrosols and derivatives, a subclass of phenols within the organic compounds. It acts as an inhibitor of the Beta-1 adrenergic receptor (ADRB1), Beta-2 adrenergic receptor (ADRB2), and Beta-3 adrenergic receptor (ADRB3).

The compound is used as a treatment for high blood pressure (PMC10301436), heart failure (PMC11550835), hypertension (PMC11550835), atrial fibrillation (PMC1492602), arrhythmia (PMC9369816), and pheochromocytoma (PMC10074227). Recorded exposure routes include oral and intravenous administration.

Metoprolol is found in or released from 17 recorded sources. Within healthcare, pharmaceuticals, and veterinary products, it is identified as a beta blocking agent. It is also associated with food preservation in the category of food, food processing, and cookware, as well as drinking water and water supply. Other recorded sources include household cleaning and consumer products—specifically bleaching agents, cigar cigarettes, non electric simulated smoking devices, other smoking requisites, and perfumes within detergents and soaps—and electrical and electronic equipment, including antennas, conductors or conductive bodies characterised by the conductive materials, electric hearing aids, electric switches, and electrically stimulated smoking devices.</description>
  <categories/>
  <types/>
  <synonyms>
    <synonym>1-[4-(2-methoxyethyl)phenoxy]-3-[(propan-2-yl)amino]propan-2-ol</synonym>
  </synonyms>
  <chemical_formula>C15H25NO3</chemical_formula>
  <average_molecular_weight>267.3639</average_molecular_weight>
  <monisotopic_moleculate_weight>267.183443671</monisotopic_moleculate_weight>
  <iupac_name>1-[4-(2-methoxyethyl)phenoxy]-3-[(propan-2-yl)amino]propan-2-ol</iupac_name>
  <traditional_iupac>metoprolol</traditional_iupac>
  <cas_registry_number>51384-51-1</cas_registry_number>
  <smiles>COCCC1=CC=C(OCC(O)CNC(C)C)C=C1</smiles>
  <inchi>InChI=1S/C15H25NO3/c1-12(2)16-10-14(17)11-19-15-6-4-13(5-7-15)8-9-18-3/h4-7,12,14,16-17H,8-11H2,1-3H3</inchi>
  <inchikey>IUBSYMUCCVWXPE-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Phenols</class>
    <sub_class>Tyrosols and derivatives</sub_class>
    <direct_parent>Tyrosols and derivatives</direct_parent>
    <alternate_parents>
      <alternative_parent>1,2-aminoalcohols</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Dialkyl ethers</alternative_parent>
      <alternative_parent>Dialkylamines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenol ethers</alternative_parent>
      <alternative_parent>Phenoxy compounds</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>Aromatic homomonocyclic compound</substituent>
      <substituent>Dialkyl ether</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary aliphatic amine</substituent>
      <substituent>Secondary amine</substituent>
      <substituent>Tyrosol derivative</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>aromatic ether</descriptor>
      <descriptor>propanolamine</descriptor>
      <descriptor>secondary alcohol</descriptor>
      <descriptor>secondary amino compound</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Metoprolol Action Pathway</name>
      <smpdb_id>SMP0000302</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Metoprolol Action Pathway (New)</name>
      <smpdb_id>SMP0126213</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Metoprolol Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0142725</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>1.76</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.80</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.82</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>4.02e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.76</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>14.09</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.67</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>1-[4-(2-methoxyethyl)phenoxy]-3-[(propan-2-yl)amino]propan-2-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>267.3639</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>267.183443671</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>COCCC1=CC=C(OCC(O)CNC(C)C)C=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C15H25NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C15H25NO3/c1-12(2)16-10-14(17)11-19-15-6-4-13(5-7-15)8-9-18-3/h4-7,12,14,16-17H,8-11H2,1-3H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>IUBSYMUCCVWXPE-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>50.72</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>76.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>31.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>9</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:0x00007f7227958210&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB00264</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>4171</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>4027</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>
