<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-25 18:12:38 UTC</creation_date>
  <update_date>2026-05-14 16:37:17 UTC</update_date>
  <accession/>
  <common_name>Phenylephrine</common_name>
  <class>SmallMolecule</class>
  <description>Phenylephrine is an organic compound with the formula C9H13NO2 and an average molecular weight of 167.21 g/mol. Phenylephrine belongs to the 1-hydroxy-4-unsubstituted benzenoids, a subclass of phenols within the organic compounds. It is recorded as an agonist for the D(2) dopamine receptor (DRD2) as well as the Alpha-1A, Alpha-1B, and Alpha-1D adrenergic receptors (ADRA1A, ADRA1B, and ADRA1D).

The compound is found in or released from 24 recorded sources across several categories. Within healthcare, pharmaceuticals, and veterinary products, it is used in nasal preparations, decongestants and antiallergics, mydriatics and cycloplegics, vasoprotectives, and cardiac stimulants excluding cardiac glycosides. In the context of food and food processing, it is associated with food preservation, the preparation of vinegar, and fermentation processes for beer. It is also found in drinking water, ceilings, and various household cleaning and consumer products, including perfumes within detergents and soaps, tobacco product cases, cigar cigarettes, non electric simulated smoking devices, and other smoking requisites. Additionally, it is found in electrical and electronic equipment, such as electrodes, electrically stimulated smoking devices, electric hearing aids, communication cables or conductors, and conductors or conductive bodies characterised by the conductive materials. Recorded exposure routes for phenylephrine include oral, nasal, ophthalmic, intraocular, auricular, intravenous, intramuscular, subcutaneous, rectal, respiratory, topical, and irrigation.</description>
  <categories/>
  <types/>
  <synonyms/>
  <chemical_formula>C9H13NO2</chemical_formula>
  <average_molecular_weight>167.205</average_molecular_weight>
  <monisotopic_moleculate_weight>167.094628665</monisotopic_moleculate_weight>
  <iupac_name>3-[(1R)-1-hydroxy-2-(methylamino)ethyl]phenol</iupac_name>
  <traditional_iupac>phenylephrine</traditional_iupac>
  <cas_registry_number>59-42-7</cas_registry_number>
  <smiles>CNC[C@H](O)C1=CC(O)=CC=C1</smiles>
  <inchi>InChI=1S/C9H13NO2/c1-10-6-9(12)7-3-2-4-8(11)5-7/h2-5,9-12H,6H2,1H3/t9-/m0/s1</inchi>
  <inchikey>SONNWYBIRXJNDC-VIFPVBQESA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Phenols</class>
    <sub_class>1-hydroxy-4-unsubstituted benzenoids</sub_class>
    <direct_parent>1-hydroxy-4-unsubstituted benzenoids</direct_parent>
    <alternate_parents>
      <alternative_parent>1,2-aminoalcohols</alternative_parent>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Aromatic alcohols</alternative_parent>
      <alternative_parent>Benzene and substituted derivatives</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>1-hydroxy-2-unsubstituted benzenoid</substituent>
      <substituent>1-hydroxy-4-unsubstituted benzenoid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Amine</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic alcohol</substituent>
      <substituent>Aromatic homomonocyclic compound</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>Secondary alcohol</substituent>
      <substituent>Secondary aliphatic amine</substituent>
      <substituent>Secondary amine</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>phenylethanolamines</descriptor>
      <descriptor>secondary amino compound</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Phenylephrine Action Pathway</name>
      <smpdb_id>SMP0125242</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Phenylephrine Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0142845</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>-0.07</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.69</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.88</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.20e+01 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>9.07</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-[(1R)-1-hydroxy-2-(methylamino)ethyl]phenol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>167.205</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>167.094628665</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CNC[C@H](O)C1=CC(O)=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H13NO2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H13NO2/c1-10-6-9(12)7-3-2-4-8(11)5-7/h2-5,9-12H,6H2,1H3/t9-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SONNWYBIRXJNDC-VIFPVBQESA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>52.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>47.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>18.2</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>3</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:0x00007f7224703030&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB00388</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>6041</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>5818</chemspider_id>
  <kegg_id/>
  <uniprot_id/>
  <omim_id/>
  <chebi_id/>
  <biocyc_id/>
  <ctd_id/>
  <stitch_id/>
  <actor_id/>
  <pdb_id/>
  <wikipidia/>
  <general_references/>
  <targets>
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  </targets>
</compound>
