<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 04:28:32 UTC</creation_date>
  <update_date>2026-08-19 17:11:05 UTC</update_date>
  <accession/>
  <common_name>Oxymetazoline</common_name>
  <class>SmallMolecule</class>
  <description>Oxymetazoline is an organic compound with the formula C16H24N2O and an average molecular weight of 260.37 g/mol. Oxymetazoline belongs to the xylenes, a subclass of benzene and substituted derivatives within the organic compounds.

This compound is found in or released from 16 recorded sources. These include healthcare, pharmaceuticals, and veterinary products such as decongestants, antiallergics, nasal preparations, and dermatological preparations. It is also associated with household cleaning and consumer products, specifically perfumes within detergents and soaps, soap detergents, cigar cigarettes, other smoking requisites, and non electric simulated smoking devices. Additionally, it is linked to electrical and electronic equipment, including electrodes, power cables, hybrid capacitors, electric hearing aids, and electrically stimulated smoking devices. Other recorded sources include food preservation within food, food processing, and cookware, as well as stairs and ramps within building and construction. Recorded exposure routes for oxymetazoline include oral, nasal, topical, and ophthalmic pathways.

At the molecular level, oxymetazoline interacts with 10 recorded protein targets. It acts as an agonist or partial agonist of the Alpha-1A adrenergic receptor (ADRA1A), as well as the Alpha-2A (ADRA2A), Alpha-2B (ADRA2B), and Alpha-2C (ADRA2C) adrenergic receptors, among six other proteins.</description>
  <categories/>
  <types/>
  <synonyms/>
  <chemical_formula>C16H24N2O</chemical_formula>
  <average_molecular_weight>260.3746</average_molecular_weight>
  <monisotopic_moleculate_weight>260.1888634</monisotopic_moleculate_weight>
  <iupac_name>6-tert-butyl-3-(4,5-dihydro-1H-imidazol-2-ylmethyl)-2,4-dimethylphenol</iupac_name>
  <traditional_iupac>oxymetazoline</traditional_iupac>
  <cas_registry_number>1491-59-4</cas_registry_number>
  <smiles>CC1=CC(=C(O)C(C)=C1CC1=NCCN1)C(C)(C)C</smiles>
  <inchi>InChI=1S/C16H24N2O/c1-10-8-13(16(3,4)5)15(19)11(2)12(10)9-14-17-6-7-18-14/h8,19H,6-7,9H2,1-5H3,(H,17,18)</inchi>
  <inchikey>WYWIFABBXFUGLM-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Xylenes</sub_class>
    <direct_parent>Xylenols</direct_parent>
    <alternate_parents>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Carboxamidines</alternative_parent>
      <alternative_parent>Carboximidamides</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Imidazolines</alternative_parent>
      <alternative_parent>Imidolactams</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Ortho cresols</alternative_parent>
      <alternative_parent>Para cresols</alternative_parent>
      <alternative_parent>Phenylpropanes</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
      <alternative_parent>m-Xylenes</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>2-imidazoline</substituent>
      <substituent>Amidine</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carboximidamide</substituent>
      <substituent>Carboxylic acid amidine</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>M-xylene</substituent>
      <substituent>O-cresol</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>P-cresol</substituent>
      <substituent>Phenol</substituent>
      <substituent>Phenylpropane</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Xylenol</substituent>
    </substituents>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>carboxamidine</descriptor>
      <descriptor>imidazolines</descriptor>
      <descriptor>phenols</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Oxymetazoline Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0143367</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>3.03</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.70</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.70</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>5.15e-02 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>3.03</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>10.91</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>10.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>6-tert-butyl-3-(4,5-dihydro-1H-imidazol-2-ylmethyl)-2,4-dimethylphenol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>260.3746</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>260.1888634</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC1=CC(=C(O)C(C)=C1CC1=NCCN1)C(C)(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C16H24N2O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C16H24N2O/c1-10-8-13(16(3,4)5)15(19)11(2)12(10)9-14-17-6-7-18-14/h8,19H,6-7,9H2,1-5H3,(H,17,18)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>WYWIFABBXFUGLM-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>44.62</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>79.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>30.64</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>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:0x00007f72251f7e50&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB00935</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>4636</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>4475</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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  </targets>
</compound>
