<?xml version="1.0" encoding="UTF-8"?>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-10-03 18:32:52 UTC</creation_date>
  <update_date>2020-04-22 15:48:37 UTC</update_date>
  <accession>BMDB0012128</accession>
  <secondary_accessions>
    <accession>BMDB12128</accession>
  </secondary_accessions>
  <name>(R)-Amphetamine</name>
  <description/>
  <synonyms>
    <synonym>(-)-Amphetamine</synonym>
    <synonym>(-)-Phenylisopropylamine</synonym>
    <synonym>(R)-alpha-Methylbenzeneethanamine</synonym>
    <synonym>(R)-alpha-Methylphenethylamine</synonym>
    <synonym>Levamfetamine</synonym>
    <synonym>Levamphetamine</synonym>
    <synonym>(R)-a-Methylbenzeneethanamine</synonym>
    <synonym>(R)-Α-methylbenzeneethanamine</synonym>
    <synonym>(R)-a-Methylphenethylamine</synonym>
    <synonym>(R)-Α-methylphenethylamine</synonym>
    <synonym>Amfetamine</synonym>
    <synonym>Amphetamine</synonym>
    <synonym>Amphetamine sulfate</synonym>
    <synonym>Amphetamine sulfate (2:1)</synonym>
    <synonym>Centramina</synonym>
    <synonym>Desoxynorephedrin</synonym>
    <synonym>Fenamine</synonym>
    <synonym>Levoamphetamine</synonym>
    <synonym>Mydrial</synonym>
    <synonym>Phenamine</synonym>
    <synonym>Phenopromin</synonym>
    <synonym>Sulfate, amphetamine</synonym>
    <synonym>Thyramine</synonym>
    <synonym>L Amphetamine</synonym>
    <synonym>Levo amphetamine</synonym>
    <synonym>Levo-amphetamine</synonym>
    <synonym>(R)-a-Methyl-benzeneethanamine</synonym>
    <synonym>(R)-alpha-Methyl-benzeneethanamine</synonym>
    <synonym>(R)-Phenaminum</synonym>
    <synonym>(R)-Phenylisopropylamine</synonym>
    <synonym>L-(R)-Amphetamine</synonym>
    <synonym>L-a-Methylphenethylamine</synonym>
    <synonym>L-alpha-Methylphenethylamine</synonym>
    <synonym>L-Amphetamine</synonym>
    <synonym>Miquel brand OF amfetamine sulfate</synonym>
  </synonyms>
  <chemical_formula>C9H13N</chemical_formula>
  <average_molecular_weight>135.2062</average_molecular_weight>
  <monisotopic_moleculate_weight>135.104799421</monisotopic_moleculate_weight>
  <iupac_name>(2R)-1-phenylpropan-2-amine</iupac_name>
  <traditional_iupac>(-)-amphetamine</traditional_iupac>
  <cas_registry_number>156-34-3</cas_registry_number>
  <smiles>C[C@@H](N)CC1=CC=CC=C1</smiles>
  <inchi>InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3/t8-/m1/s1</inchi>
  <inchikey>KWTSXDURSIMDCE-MRVPVSSYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Phenethylamines</sub_class>
    <direct_parent>Amphetamines and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monoalkylamines</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenylpropanes</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Amine</substituent>
      <substituent>Amphetamine or derivatives</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenylpropane</substituent>
      <substituent>Primary aliphatic amine</substituent>
      <substituent>Primary amine</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>amphetamine</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.85</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.89</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.8</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>10.01</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2R)-1-phenylpropan-2-amine</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>135.2062</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>135.104799421</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[C@@H](N)CC1=CC=CC=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C9H13N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3/t8-/m1/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>KWTSXDURSIMDCE-MRVPVSSYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>26.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>43.71</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.18</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>1</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>
    <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::MsIr</type>
      <spectrum_id>14</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>2631</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>2632</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>2633</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>17913</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>146884</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305689</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305690</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>305691</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>349147</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>349148</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>349149</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2705705</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2705706</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2705707</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3003747</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3003748</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>3003749</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>95398</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>95399</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>95400</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>95401</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>95402</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>95403</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>95404</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>95405</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>95406</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>95407</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>95408</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>95409</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>95410</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>95411</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>95412</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>95413</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>95414</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>95415</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>95416</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>95417</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB028792</foodb_id>
  <chemspider_id>30477</chemspider_id>
  <pubchem_compound_id>32893</pubchem_compound_id>
  <kegg_id>C07514</kegg_id>
  <chebi_id>42724</chebi_id>
  <pdbe_id>FRD</pdbe_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id>CPD-7659</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
