<?xml version="1.0" encoding="UTF-8"?>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 23:01:47 UTC</creation_date>
  <update_date>2020-04-22 15:11:27 UTC</update_date>
  <accession>BMDB0002832</accession>
  <secondary_accessions>
    <accession>BMDB02832</accession>
  </secondary_accessions>
  <name>Methylnoradrenaline</name>
  <description/>
  <synonyms>
    <synonym>alpha-Methylnorepinephrine</synonym>
    <synonym>alpha-Methylnoradrenaline</synonym>
    <synonym>a-Methylnorepinephrine</synonym>
    <synonym>Α-methylnorepinephrine</synonym>
    <synonym>a-Methylnoradrenaline</synonym>
    <synonym>Α-methylnoradrenaline</synonym>
    <synonym>(+-)-3,4-Dihydroxynorephedrine</synonym>
    <synonym>(+/-)-3,4-dihydroxynorephedrine</synonym>
    <synonym>3,4-Dihydrophenyl-1-amino-2-propanol-1</synonym>
    <synonym>Dihydroxyphenylpropanolamine</synonym>
    <synonym>Dioxynorepinephrine</synonym>
    <synonym>DL-a-Methylnorepinephrine</synonym>
    <synonym>DL-alpha-Methylnorepinephrine</synonym>
    <synonym>Isoadrenaline</synonym>
    <synonym>L-a-Methylnorepinephrine</synonym>
    <synonym>L-alpha-Methylnorepinephrine</synonym>
    <synonym>Levonordefrin</synonym>
    <synonym>Nordefrin</synonym>
    <synonym>Nordefrin hydrochloride, (r*,r*)-(+,-)-isomer</synonym>
    <synonym>Nordefrin, (r*,r*)-isomer</synonym>
    <synonym>3,4-Dihydroxynorephedrine</synonym>
    <synonym>Cobefrine</synonym>
    <synonym>Corbadrine</synonym>
    <synonym>Nordefrin tartrate, (r*,r*), (r*,r*) isomer</synonym>
    <synonym>4-(2-amino-1-Hydroxypropyl)-1,2-benzenediol</synonym>
    <synonym>4-(2-amino-1-Hydroxypropyl)-1,2-benzenediol hydrochloride, (r*,r*)-(+,-)-isomer</synonym>
    <synonym>4-(2-amino-1-Hydroxypropyl)-1,2-benzenediol hydrochloride, (r*,s*)-(+-)-isomer</synonym>
    <synonym>NeoCobefrin</synonym>
    <synonym>alpha Methylnoradrenaline</synonym>
    <synonym>3,4 Dihydroxynorephedrine</synonym>
    <synonym>4-(2-amino-1-Hydroxypropyl)-1,2-benzenediol, (r*,r*)-isomer</synonym>
    <synonym>4-(2-amino-1-Hydroxypropyl)-1,2-benzenediol, (r*,s*)-isomer</synonym>
    <synonym>Hydrochloride, nordefrin</synonym>
    <synonym>neo-Cobefrin</synonym>
    <synonym>Nordefrin hydrochloride</synonym>
    <synonym>Nordefrin tartrate, (r*,s*), (r*,r*) isomer</synonym>
    <synonym>Nordefrin, (r*,s*)-isomer</synonym>
    <synonym>alpha Methylnorepinephrine</synonym>
    <synonym>4-(2-amino-1-Hydroxypropyl)-1,2-benzenediol tartrate, (r*,s*), (r*,r*)-isomer</synonym>
    <synonym>Methylnorepinephrine</synonym>
    <synonym>Norephrine</synonym>
    <synonym>4-(2-amino-1-Hydroxypropyl)-1,2-benzenediol tartrate, (r*,r*), (r*,r*)-isomer</synonym>
    <synonym>neo Cobefrin</synonym>
    <synonym>Nordefrin hydrochloride, (r*,s*)-(+,-)-isomer</synonym>
  </synonyms>
  <chemical_formula>C9H13NO3</chemical_formula>
  <average_molecular_weight>183.2044</average_molecular_weight>
  <monisotopic_moleculate_weight>183.089543287</monisotopic_moleculate_weight>
  <iupac_name>4-(2-amino-1-hydroxypropyl)benzene-1,2-diol</iupac_name>
  <traditional_iupac>α methylnoradrenaline</traditional_iupac>
  <cas_registry_number>6539-57-7</cas_registry_number>
  <smiles>CC(N)C(O)C1=CC(O)=C(O)C=C1</smiles>
  <inchi>InChI=1S/C9H13NO3/c1-5(10)9(13)6-2-3-7(11)8(12)4-6/h2-5,9,11-13H,10H2,1H3</inchi>
  <inchikey>GEFQWZLICWMTKF-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Phenylpropanes</sub_class>
    <direct_parent>Phenylpropanes</direct_parent>
    <alternative_parents>
      <alternative_parent>1,2-aminoalcohols</alternative_parent>
      <alternative_parent>1-hydroxy-2-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>1-hydroxy-4-unsubstituted benzenoids</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Aromatic alcohols</alternative_parent>
      <alternative_parent>Catechols</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</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>Catechol</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenol</substituent>
      <substituent>Phenylpropane</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>catecholamine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>logp</kind>
      <value>-1.43</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.77</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.10</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-0.39</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>9.63</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-(2-amino-1-hydroxypropyl)benzene-1,2-diol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>183.2044</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>183.089543287</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CC(N)C(O)C1=CC(O)=C(O)C=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H13NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H13NO3/c1-5(10)9(13)6-2-3-7(11)8(12)4-6/h2-5,9,11-13H,10H2,1H3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>GEFQWZLICWMTKF-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>86.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>48.87</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>18.79</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>4</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>
    <property>
      <kind>number_of_rings</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>25309</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>38484</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>168949</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>322030</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>322031</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>322032</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>369817</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>369818</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>369819</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2800840</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2800841</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2800842</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2878667</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2878668</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2878669</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB023071</foodb_id>
  <chemspider_id>3780</chemspider_id>
  <pubchem_compound_id>3917</pubchem_compound_id>
  <pdbe_id/>
  <chebi_id>142891</chebi_id>
  <kegg_id>C17925</kegg_id>
  <drugbank_id/>
  <knapsack_id/>
  <phenol_explorer_compound_id/>
  <meta_cyc_id/>
  <bigg_id/>
  <wikipedia_id>Corbadrine</wikipedia_id>
  <metlin_id>1217</metlin_id>
  <synthesis_reference>Farrugia, M. T.; Hunter, W. H.; Kirk, G.  Preparation and pharmacological properties of y-corbasil.    Journal of Pharmacy and Pharmacology  (1969),  21(Suppl.),  199-205.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
