<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-25 03:16:00 UTC</creation_date>
  <update_date>2026-08-19 16:50:17 UTC</update_date>
  <accession/>
  <common_name>Propranolol</common_name>
  <class>SmallMolecule</class>
  <description>Propranolol (C16H21NO2) is an organic compound with an average molecular weight of 259.34 g/mol. Propranolol belongs to the naphthalenes, a class of benzenoids within the organic compounds. It is used as a biological drug (PMC7753967) and is specifically utilized as a treatment for hypertension (PMC10384072). The compound acts as an antagonist for the Beta-1 adrenergic receptor (ADRB1), Beta-2 adrenergic receptor (ADRB2), Beta-3 adrenergic receptor (ADRB3), and the 5-hydroxytryptamine receptor 1A (HTR1A), among one other protein.

Propranolol is found in or released from 23 recorded sources. These include healthcare, pharmaceuticals, and veterinary products as beta blocking agents, as well as drinking water and water supply. Other sources include food, food processing and cookware—specifically the treatment of hops, food preservation, and fermentation processes for beer—and household cleaning and consumer products such as bleaching agents, perfumes within detergents and soaps, cigar cigarettes, non electric simulated smoking devices, and other smoking requisites. It is also associated with electrical and electronic equipment, including electrodes, electric hearing aids, antennas, conductors or conductive bodies characterised by the conductive materials, and electrically stimulated smoking devices. Recorded exposure routes for the compound include oral and intravenous administration.

Health effects associated with propranolol include increases in obesity (PMC11995813) and weight gain (PMC11995813). Additionally, it is associated with hypoglycemia, hypotension, bradycardia, and bronchospasm (PMC11172932).</description>
  <categories/>
  <types/>
  <synonyms/>
  <chemical_formula>C16H21NO2</chemical_formula>
  <average_molecular_weight>259.3434</average_molecular_weight>
  <monisotopic_moleculate_weight>259.157228921</monisotopic_moleculate_weight>
  <iupac_name>1-(naphthalen-1-yloxy)-3-[(propan-2-yl)amino]propan-2-ol</iupac_name>
  <traditional_iupac>propranolol</traditional_iupac>
  <cas_registry_number>525-66-6</cas_registry_number>
  <smiles>CC(C)NCC(O)COC1=CC=CC2=CC=CC=C12</smiles>
  <inchi>InChI=1S/C16H21NO2/c1-12(2)17-10-14(18)11-19-16-9-5-7-13-6-3-4-8-15(13)16/h3-9,12,14,17-18H,10-11H2,1-2H3</inchi>
  <inchikey>AQHHHDLHHXJYJD-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Naphthalenes</class>
    <sub_class/>
    <direct_parent>Naphthalenes</direct_parent>
    <alternate_parents>
      <alternative_parent>1,2-aminoalcohols</alternative_parent>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Dialkylamines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organopnictogen 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 homopolycyclic compound</substituent>
      <substituent>Ether</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Naphthalene</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Secondary aliphatic amine</substituent>
      <substituent>Secondary amine</substituent>
    </substituents>
    <molecular_framework>Aromatic homopolycyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>naphthalenes</descriptor>
      <descriptor>propanolamine</descriptor>
      <descriptor>secondary amine</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Propranolol Action Pathway</name>
      <smpdb_id>SMP0000307</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Propranolol B1-Adrenergic Cardiac Muscle Relaxation Action Pathway</name>
      <smpdb_id>SMP0126225</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Propranolol B2-Adrenergic Vasoconstriction Action Pathway</name>
      <smpdb_id>SMP0126650</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Propranolol Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0143020</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>2.58</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.03</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.51</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>7.94e-02 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.58</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-(naphthalen-1-yloxy)-3-[(propan-2-yl)amino]propan-2-ol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>259.3434</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>259.157228921</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(C)NCC(O)COC1=CC=CC2=CC=CC=C12</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C16H21NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C16H21NO2/c1-12(2)17-10-14(18)11-19-16-9-5-7-13-6-3-4-8-15(13)16/h3-9,12,14,17-18H,10-11H2,1-2H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>AQHHHDLHHXJYJD-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>41.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>76.83</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>29.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</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:0x00007f7267488f38&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB00571</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>4946</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>4777</chemspider_id>
  <kegg_id/>
  <uniprot_id/>
  <omim_id/>
  <chebi_id/>
  <biocyc_id/>
  <ctd_id/>
  <stitch_id/>
  <actor_id/>
  <pdb_id/>
  <wikipidia/>
  <general_references/>
  <targets>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0000172</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0000694</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0001012</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0000291</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0000797</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
  </targets>
</compound>
