<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2011-09-21 00:21:12 UTC</creation_date>
  <update_date>2015-10-09 22:31:29 UTC</update_date>
  <accession>FDB022891</accession>
  <name>Phenylephrine</name>
  <description>An alpha-adrenergic agonist used as a mydriatic, nasal decongestant, and cardiotonic agent (PubChem).
Phenylephrine is used as a decongestant, available as an oral medicine or as a nasal spray. Phenylephrine is not the most common over-the-counter (OTC) decongestant (wikipedia) [HMDB]</description>
  <synonyms>
    <synonym>(-)-m-Hydroxy-a-(methylaminomethyl)benzyl alcohol</synonym>
    <synonym>(-)-m-Hydroxy-alpha-(methylaminomethyl)benzyl alcohol</synonym>
    <synonym>(-)-m-Hydroxy-α-(methylaminomethyl)benzyl alcohol</synonym>
    <synonym>Adrianol</synonym>
    <synonym>Ak-Dilate</synonym>
    <synonym>Ak-Nefrin</synonym>
    <synonym>Alcon efrin</synonym>
    <synonym>Alconefrin Nasal Drops 12</synonym>
    <synonym>Alconefrin Nasal Drops 25</synonym>
    <synonym>Alconefrin Nasal Drops 50</synonym>
    <synonym>Alconefrin Nasal Spray 25</synonym>
    <synonym>Biomydrin</synonym>
    <synonym>Dilatair</synonym>
    <synonym>Dionephrine</synonym>
    <synonym>Doktors</synonym>
    <synonym>Duration</synonym>
    <synonym>Fenilefrina</synonym>
    <synonym>I-Phrine</synonym>
    <synonym>Isophrim</synonym>
    <synonym>Isophrin</synonym>
    <synonym>Isopto Frin</synonym>
    <synonym>L-(3-Hydroxyphenyl)-N-methylethanolamine</synonym>
    <synonym>m-Methylaminoethanolphenol</synonym>
    <synonym>m-Oxedrine</synonym>
    <synonym>m-Sympathol</synonym>
    <synonym>m-Sympatol</synonym>
    <synonym>m-Synephrine</synonym>
    <synonym>Mesaton</synonym>
    <synonym>Mesatone</synonym>
    <synonym>Mesatonum</synonym>
    <synonym>Metaoxedrin</synonym>
    <synonym>Metaoxedrine</synonym>
    <synonym>Metaoxedrinum</synonym>
    <synonym>Metasympatol</synonym>
    <synonym>Metasynephrine</synonym>
    <synonym>Mezaton</synonym>
    <synonym>Minims Phenylephrine</synonym>
    <synonym>Mydfrin</synonym>
    <synonym>Neo-Synephrine</synonym>
    <synonym>Neo-Synephrine Nasal Drops</synonym>
    <synonym>Neo-Synephrine Nasal Jelly</synonym>
    <synonym>Neo-Synephrine Nasal Spray</synonym>
    <synonym>Neo-Synephrine Pediatric Nasal Drops</synonym>
    <synonym>Neofrin</synonym>
    <synonym>Neophryn</synonym>
    <synonym>Neosynephrine</synonym>
    <synonym>Nostril</synonym>
    <synonym>Nostril Spray Pump</synonym>
    <synonym>Nostril Spray Pump Mild</synonym>
    <synonym>Ocu-Phrin Sterile Eye Drops</synonym>
    <synonym>Ocu-Phrin Sterile Ophthalmic Solution</synonym>
    <synonym>Ocugestrin</synonym>
    <synonym>Phenoptic</synonym>
    <synonym>Phenylephrinum</synonym>
    <synonym>Prefrin</synonym>
    <synonym>Prefrin Liquifilm</synonym>
    <synonym>Pyracort D</synonym>
    <synonym>R(-)-Mezaton</synonym>
    <synonym>R(-)-Phenylephrine</synonym>
    <synonym>Relief Eye Drops for Red Eyes</synonym>
    <synonym>Rhinall</synonym>
    <synonym>Spersaphrine</synonym>
    <synonym>Vicks Sinex</synonym>
    <synonym>Visadron</synonym>
  </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>
    <description> belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position.</description>
    <direct_parent>1-hydroxy-4-unsubstituted benzenoids</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Phenols</class>
    <sub_class>1-hydroxy-4-unsubstituted benzenoids</sub_class>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <alternative_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>
    </alternative_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>
    <external_descriptors>
      <external_descriptor>phenylethanolamines</external_descriptor>
      <external_descriptor>secondary amino compound</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <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>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <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>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1800</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>808</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>809</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>6713</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30225</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>30747</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38301</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>146247</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>1666</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>1667</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>1668</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>1861</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>10182</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>10183</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>10184</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>10185</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>10186</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>10187</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>10188</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>10189</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>10190</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>10191</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>10192</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>10193</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>10194</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>10195</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>10196</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>10197</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>10198</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>10199</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>10200</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>10201</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2022</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2023</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2024</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5732</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5733</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5734</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5735</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5736</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5737</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5738</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5739</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5740</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5741</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>5744</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>249255</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>249256</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>249257</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>269196</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>269197</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>269198</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438305</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438306</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438307</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438308</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>438309</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB02182</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce32635fa0&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32635de8&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32635c30&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32635a78&gt;</reference>
    <reference>#&lt;Reference:0x000055ce326358c0&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32635708&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32635550&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32635370&gt;</reference>
    <reference>#&lt;Reference:0x000055ce326351b8&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32635000&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32634e48&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32634c90&gt;</reference>
    <reference>#&lt;Reference:0x000055ce32634ad8&gt;</reference>
  </general_references>
  <foods>
  </foods>
  <flavors>
    <flavor>
      <name>bitter</name>
    </flavor>
  </flavors>
  <enzymes>
    <enzyme>
      <name>Alpha-2A adrenergic receptor</name>
      <uniprot_id>P08913</uniprot_id>
      <uniprot_name/>
      <gene_name>ADRA2A</gene_name>
    </enzyme>
    <enzyme>
      <name>Alpha-2B adrenergic receptor</name>
      <uniprot_id>P18089</uniprot_id>
      <uniprot_name/>
      <gene_name>ADRA2B</gene_name>
    </enzyme>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
