<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-25 18:22:44 UTC</creation_date>
  <update_date>2026-08-19 02:02:46 UTC</update_date>
  <accession/>
  <common_name>Prilocaine</common_name>
  <class>SmallMolecule</class>
  <description>Prilocaine is an organic compound with the chemical formula C13H20N2O and an average molecular weight of 220.31 g/mol. Prilocaine belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. It acts as an inhibitor of the sodium channel protein type 5 subunit alpha (SCN5A).

The substance is identified in eleven recorded sources. Within healthcare, pharmaceuticals, and veterinary products, it is used as an anesthetic. It is also associated with food preservation in food, food processing, and cookware. Other recorded sources include household cleaning and consumer products—specifically perfumes within detergents and soaps, tobacco smoke filters, cigar cigarettes, other smoking requisites, and non-electric simulated smoking devices—as well as electrical and electronic equipment, including video games, electric hearing aids, electrically stimulated smoking devices, and conductors or conductive bodies characterised by the conductive materials.

Exposure to prilocaine occurs through multiple recorded routes. These include intravenous, intramuscular, subcutaneous, and intra-articular infiltration, as well as oral, dental, periodontal, submucosal, topical, and cutaneous administration.</description>
  <categories/>
  <types>
    <type>Human Neurotoxin</type>
  </types>
  <synonyms/>
  <chemical_formula>C13H20N2O</chemical_formula>
  <average_molecular_weight>220.3107</average_molecular_weight>
  <monisotopic_moleculate_weight>220.157563272</monisotopic_moleculate_weight>
  <iupac_name>N-(2-methylphenyl)-2-(propylamino)propanamide</iupac_name>
  <traditional_iupac>prilocaine</traditional_iupac>
  <cas_registry_number>721-50-6</cas_registry_number>
  <smiles>CCCNC(C)C(=O)NC1=CC=CC=C1C</smiles>
  <inchi>InChI=1S/C13H20N2O/c1-4-9-14-11(3)13(16)15-12-8-6-5-7-10(12)2/h5-8,11,14H,4,9H2,1-3H3,(H,15,16)</inchi>
  <inchikey>MVFGUOIZUNYYSO-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic acids and derivatives</super_class>
    <class>Carboxylic acids and derivatives</class>
    <sub_class>Amino acids, peptides, and analogues</sub_class>
    <direct_parent>Alpha amino acid amides</direct_parent>
    <alternate_parents>
      <alternative_parent>Alanine and derivatives</alternative_parent>
      <alternative_parent>Anilides</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Dialkylamines</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>N-arylamides</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Toluenes</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Alanine or derivatives</substituent>
      <substituent>Alpha-amino acid amide</substituent>
      <substituent>Amine</substituent>
      <substituent>Anilide</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>N-arylamide</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Secondary aliphatic amine</substituent>
      <substituent>Secondary amine</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Toluene</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>amino acid amide</descriptor>
      <descriptor>monocarboxylic acid amide</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Prilocaine Action Pathway</name>
      <smpdb_id>SMP0000401</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Prilocaine Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0143193</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>2.68</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.87</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.83</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>3.26e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.68</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>13.51</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.82</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>N-(2-methylphenyl)-2-(propylamino)propanamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>220.3107</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>220.157563272</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCCNC(C)C(=O)NC1=CC=CC=C1C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C13H20N2O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C13H20N2O/c1-4-9-14-11(3)13(16)15-12-8-6-5-7-10(12)2/h5-8,11,14H,4,9H2,1-3H3,(H,15,16)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>MVFGUOIZUNYYSO-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>41.13</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>67.86</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>25.98</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>5</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</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:0x00007f86bb258660&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB00750</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>4906</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>4737</chemspider_id>
  <kegg_id/>
  <uniprot_id/>
  <omim_id/>
  <chebi_id/>
  <biocyc_id/>
  <ctd_id/>
  <stitch_id/>
  <actor_id/>
  <pdb_id/>
  <wikipidia/>
  <general_references/>
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      <target_id>BE0000197</target_id>
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  </targets>
</compound>
