<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-26 02:27:27 UTC</creation_date>
  <update_date>2026-04-05 17:28:18 UTC</update_date>
  <accession/>
  <common_name>xi-Norepinephrine</common_name>
  <class>SmallMolecule</class>
  <description>xi-Norepinephrine is an organic compound with the formula C8H11NO3 and an average molecular weight of 169.18 g/mol. xi-Norepinephrine belongs to the benzenediols, a subclass of phenols within the organic compounds.

This compound is found in or released from 27 recorded sources across several categories. Within electrical and electronic equipment, it is associated with amplifiers, antennas, auxiliary devices, electric hearing aids, and conductors or conductive bodies characterised by the conductive materials. In the context of household cleaning and consumer products, it is linked to cigar cigarettes, non electric simulated smoking devices, other smoking requisites, pipe accessories, and perfumes within detergents and soaps, among four other sources. Regarding food, food processing and cookware, the compound is identified in food preservation, the preparation of vinegar, and fermentation processes for beer. Additionally, it is found in building and construction materials, specifically ladders and ceilings.</description>
  <categories/>
  <types/>
  <synonyms/>
  <chemical_formula>C8H11NO3</chemical_formula>
  <average_molecular_weight>169.1778</average_molecular_weight>
  <monisotopic_moleculate_weight>169.073893223</monisotopic_moleculate_weight>
  <iupac_name>4-[(1R)-2-amino-1-hydroxyethyl]benzene-1,2-diol</iupac_name>
  <traditional_iupac>norepinephrine</traditional_iupac>
  <cas_registry_number>586-17-4</cas_registry_number>
  <smiles>NCC(O)C1=CC(O)=C(O)C=C1</smiles>
  <inchi>InChI=1S/C8H11NO3/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3,8,10-12H,4,9H2</inchi>
  <inchikey>SFLSHLFXELFNJZ-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Phenols</class>
    <sub_class>Benzenediols</sub_class>
    <direct_parent>Catechols</direct_parent>
    <alternate_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>Benzene and substituted derivatives</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>
    </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>Catechol</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>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>Adrenalines</descriptor>
      <descriptor>Biogenic amines</descriptor>
      <descriptor>noradrenaline</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways/>
  <state/>
  <appearance/>
  <experimental_properties/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-0.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>9.5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-[(1R)-2-amino-1-hydroxyethyl]benzene-1,2-diol</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>169.1778</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>169.073893223</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>NCC(O)C1=CC(O)=C(O)C=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C8H11NO3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C8H11NO3/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3,8,10-12H,4,9H2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>SFLSHLFXELFNJZ-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>44.46</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.96</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>
  </predicted_properties>
  <route_of_exposure/>
  <mechanism_of_toxicity/>
  <metabolism/>
  <toxicity/>
  <lethaldose/>
  <carcinogenicity/>
  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f72262fb198&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id/>
  <hmdb_id/>
  <pubchem_compound_id>951</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>926</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>
