<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 06:30:54 UTC</creation_date>
  <update_date>2026-08-19 05:15:20 UTC</update_date>
  <accession/>
  <common_name>Naphazoline</common_name>
  <class>SmallMolecule</class>
  <description>Naphazoline is an organic compound with the formula C14H14N2 and an average molecular weight of 210.28 g/mol. Naphazoline belongs to the naphthalenes, a class of benzenoids within the organic compounds.

The compound is associated with 16 recorded sources across several categories. In healthcare, pharmaceuticals, and veterinary products, it is found in nasal preparations as well as decongestants and antiallergics. It is also linked to food, food processing, and cookware, specifically in food preservation, the processing of meats and fish, and the preparation of sparkling wine or wine. Within household cleaning and consumer products, it is found in tobacco smoke filters, cigar cigarettes, other smoking requisites, and non-electric simulated smoking devices. Additionally, it is released from electrical and electronic equipment, including electric switches, electric hearing aids, hybrid capacitors, electrically stimulated smoking devices, and conductors or conductive bodies characterised by the conductive materials.

Naphazoline acts on three recorded protein targets, serving as an agonist of the Alpha-1A adrenergic receptor (ADRA1A), the Alpha-2A adrenergic receptor (ADRA2A), and the D(2) dopamine receptor (DRD2). Recorded exposure routes for the compound include topical, ophthalmic, and nasal application.</description>
  <categories/>
  <types/>
  <synonyms/>
  <chemical_formula>C14H14N2</chemical_formula>
  <average_molecular_weight>210.28</average_molecular_weight>
  <monisotopic_moleculate_weight>210.115698459</monisotopic_moleculate_weight>
  <iupac_name>2-[(naphthalen-2-yl)methyl]-4,5-dihydro-1H-imidazole</iupac_name>
  <traditional_iupac>2-(naphthalen-2-ylmethyl)-4,5-dihydro-1H-imidazole</traditional_iupac>
  <cas_registry_number>835-31-4</cas_registry_number>
  <smiles>C(C1=NCCN1)C1=CC2=CC=CC=C2C=C1</smiles>
  <inchi>InChI=1S/C14H14N2/c1-2-4-13-9-11(5-6-12(13)3-1)10-14-15-7-8-16-14/h1-6,9H,7-8,10H2,(H,15,16)</inchi>
  <inchikey>VIXRKFBKWOHVBR-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>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>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>2-imidazoline</substituent>
      <substituent>Amidine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Carboximidamide</substituent>
      <substituent>Carboxylic acid amidine</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Imidolactam</substituent>
      <substituent>Naphthalene</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organoheterocyclic compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
    </substituents>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <descriptors/>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Naphazoline Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0144084</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>2.19</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>3.45</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.76</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>3.68e-02 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.19</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>10.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-[(naphthalen-2-yl)methyl]-4,5-dihydro-1H-imidazole</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>210.28</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>210.115698459</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C(C1=NCCN1)C1=CC2=CC=CC=C2C=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C14H14N2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C14H14N2/c1-2-4-13-9-11(5-6-12(13)3-1)10-14-15-7-8-16-14/h1-6,9H,7-8,10H2,(H,15,16)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VIXRKFBKWOHVBR-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>24.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>65.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>23.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</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/>
  <metabolism/>
  <toxicity/>
  <lethaldose/>
  <carcinogenicity/>
  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f7279300640&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB06711</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>4436</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>4283</chemspider_id>
  <kegg_id/>
  <uniprot_id/>
  <omim_id/>
  <chebi_id/>
  <biocyc_id/>
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  <wikipidia/>
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</compound>
