<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2011-09-21 00:14:00 UTC</creation_date>
  <update_date>2025-11-19 02:41:41 UTC</update_date>
  <accession>FDB022439</accession>
  <name>Nornicotine</name>
  <description>An alkaloid extracted from tobacco and related to nicotine but having a lower toxicity: used as an agricultural and horticultural insecticide. [HMDB]</description>
  <synonyms>
    <synonym>(+-)-1'-demethyl-Nicotine</synonym>
    <synonym>(+-)-1'-Demethylnicotine</synonym>
    <synonym>(+-)-3-(2-Pyrrolidinyl)pyridine</synonym>
    <synonym>(+-)-Nornicotine</synonym>
    <synonym>(R,S)-Nornicotine</synonym>
    <synonym>(R)-3-(Pyrrolidin-2-yl)pyridine</synonym>
    <synonym>(S)-2-(3-Pyridyl)pyrrolidine</synonym>
    <synonym>2-(3-Pyridyl)pyrrolidine</synonym>
    <synonym>3-(2-Pyrrolidinyl)pyridine</synonym>
    <synonym>dl-Norcitine</synonym>
    <synonym>l-Nor-nicotine</synonym>
    <synonym>Nornicotin</synonym>
    <synonym>Nornicotine</synonym>
    <synonym>S-(-)-Nornicotine</synonym>
  </synonyms>
  <chemical_formula>C9H12N2</chemical_formula>
  <average_molecular_weight>148.205</average_molecular_weight>
  <monisotopic_moleculate_weight>148.100048394</monisotopic_moleculate_weight>
  <iupac_name>3-(pyrrolidin-2-yl)pyridine</iupac_name>
  <traditional_iupac>(+-)-nornicotine</traditional_iupac>
  <cas_registry_number>494-97-3</cas_registry_number>
  <smiles>C1CNC(C1)C1=CC=CN=C1</smiles>
  <inchi>InChI=1S/C9H12N2/c1-3-8(7-10-5-1)9-4-2-6-11-9/h1,3,5,7,9,11H,2,4,6H2</inchi>
  <inchikey>MYKUKUCHPMASKF-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrrolidinylpyridines. Pyrrolidinylpyridines are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring.</description>
    <direct_parent>Pyrrolidinylpyridines</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Pyridines and derivatives</class>
    <sub_class>Pyrrolidinylpyridines</sub_class>
    <molecular_framework>Aromatic heteromonocyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Dialkylamines</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Pyrrolidines</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Amine</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic heteromonocyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Pyrrolidine</substituent>
      <substituent>Pyrrolidinylpyridine</substituent>
      <substituent>Secondary aliphatic amine</substituent>
      <substituent>Secondary amine</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>Pyridine alkaloids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.66</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-0.76</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.60e+01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>0.78</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>10.21</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>3-(pyrrolidin-2-yl)pyridine</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>148.205</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>148.100048394</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>C1CNC(C1)C1=CC=CN=C1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C9H12N2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C9H12N2/c1-3-8(7-10-5-1)9-4-2-6-11-9/h1,3,5,7,9,11H,2,4,6H2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>MYKUKUCHPMASKF-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>24.92</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>44.36</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>16.66</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>1</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>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>146510</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>146511</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>146512</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>146513</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>146514</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>146515</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>146516</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>146517</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>146518</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>146519</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>146520</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>146521</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>146522</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>146523</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>146524</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>146525</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>146526</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>146527</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>146528</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>146529</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>1089</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>1090</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>1091</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>21286</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>32173</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99654</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>126690</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>173284</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>51672</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>51673</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>51674</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>152958</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>152959</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>152960</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441341</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441342</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441343</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441344</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>441345</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>444071</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>444072</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>444073</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>444074</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>444075</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>444076</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>444077</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>444078</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>444079</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2226584</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2228118</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2228940</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2229868</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2230517</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB01126</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>28313</chebi_id>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce31ea81c0&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31ea7f90&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31ea7d60&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31ea7b80&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31ea7950&gt;</reference>
  </general_references>
  <foods>
    <food>
      <name>Anatidae</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Anatidae</name_scientific>
      <ncbi_taxonomy_id>8830</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Beefalo</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Bos taurus X Bison bison</name_scientific>
      <ncbi_taxonomy_id>297284</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Bison</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Bison bison</name_scientific>
      <ncbi_taxonomy_id>9901</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Buffalo</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Bubalus bubalis</name_scientific>
      <ncbi_taxonomy_id>89462</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Cattle (Beef, Veal)</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Bos taurus</name_scientific>
      <ncbi_taxonomy_id>9913</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Chicken</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Gallus gallus</name_scientific>
      <ncbi_taxonomy_id>9031</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Columbidae (Dove, Pigeon)</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Columbidae</name_scientific>
      <ncbi_taxonomy_id>8930</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Deer</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Cervidae</name_scientific>
      <ncbi_taxonomy_id>9850</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Domestic goat</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Capra aegagrus hircus</name_scientific>
      <ncbi_taxonomy_id>9925</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Domestic pig</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Sus scrofa domestica</name_scientific>
      <ncbi_taxonomy_id>9825</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Elk</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Cervus canadensis</name_scientific>
      <ncbi_taxonomy_id>1574408</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Emu</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Dromaius novaehollandiae</name_scientific>
      <ncbi_taxonomy_id>8790</ncbi_taxonomy_id>
    </food>
    <food>
      <name>European rabbit</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Oryctolagus</name_scientific>
      <ncbi_taxonomy_id>9984</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Greylag goose</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Anser anser</name_scientific>
      <ncbi_taxonomy_id>8843</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Guinea hen</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Numida meleagris</name_scientific>
      <ncbi_taxonomy_id>8996</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Horse</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Equus caballus</name_scientific>
      <ncbi_taxonomy_id>9796</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Mallard duck</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Anas platyrhynchos</name_scientific>
      <ncbi_taxonomy_id>8839</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Mountain hare</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Lepus timidus</name_scientific>
      <ncbi_taxonomy_id>62621</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Mule deer</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Odocoileus</name_scientific>
      <ncbi_taxonomy_id>9871</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Ostrich</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Struthio camelus</name_scientific>
      <ncbi_taxonomy_id>8801</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Pheasant</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Phasianus colchicus</name_scientific>
      <ncbi_taxonomy_id>9054</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Quail</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Phasianidae</name_scientific>
      <ncbi_taxonomy_id>9005</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Rabbit</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Leporidae</name_scientific>
      <ncbi_taxonomy_id>9979</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Rock ptarmigan</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Lagopus muta</name_scientific>
      <ncbi_taxonomy_id>64668</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Sheep (Mutton, Lamb)</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Ovis aries</name_scientific>
      <ncbi_taxonomy_id>9940</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Squab</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Columba</name_scientific>
      <ncbi_taxonomy_id>8931</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Turkey</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Meleagris gallopavo</name_scientific>
      <ncbi_taxonomy_id>9103</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Velvet duck</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Melanitta fusca</name_scientific>
      <ncbi_taxonomy_id>371864</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Wild boar</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Sus scrofa</name_scientific>
      <ncbi_taxonomy_id>9823</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
