<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 05:02:43 UTC</creation_date>
  <update_date>2026-08-19 07:15:25 UTC</update_date>
  <accession/>
  <common_name>Metoclopramide</common_name>
  <class>SmallMolecule</class>
  <description>Metoclopramide is an organic compound with the formula C14H22ClN3O2 and an average molecular weight of 299.80 g/mol. Metoclopramide belongs to the aminophenyl ethers, a subclass of phenol ethers within the organic compounds. It has been recorded in 19 different sources, including healthcare, pharmaceuticals &amp; veterinary products (Propulsives), food, food processing &amp; cookware (Food Preservation, Preparation Of Vinegar), household cleaning &amp; consumer products (Cigar Cigarettes, Non Electric Simulated Smoking Devices, Other Smoking Requisites, Perfumes Within Detergents And Soaps, Soap Detergents, and 2 more), and electrical &amp; electronic equipment (Conductors Or Conductive Bodies Characterised By The Conductive Materials, Electric Hearing Aids, Electrically Stimulated Smoking Devices, Electrodes, Hybrid Capacitors, and 4 more). Recorded exposure routes for the compound include oral, nasal, intravenous, and intramuscular administration.

The compound interacts with four recorded protein targets, acting as an agonist/antagonist of the D(2) dopamine receptor (DRD2), 5-hydroxytryptamine receptor 4 (HTR4), 5-hydroxytryptamine receptor 3A (HTR3A), and Muscarinic acetylcholine receptor M1 (CHRM1). In terms of health effects, metoclopramide has a therapeutic effect on nausea (PMC11340200).</description>
  <categories/>
  <types/>
  <synonyms/>
  <chemical_formula>C14H22ClN3O2</chemical_formula>
  <average_molecular_weight>299.796</average_molecular_weight>
  <monisotopic_moleculate_weight>299.14005467</monisotopic_moleculate_weight>
  <iupac_name>4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzamide</iupac_name>
  <traditional_iupac>metoclopramide</traditional_iupac>
  <cas_registry_number>364-62-5</cas_registry_number>
  <smiles>CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC</smiles>
  <inchi>InChI=1S/C14H22ClN3O2/c1-4-18(5-2)7-6-17-14(19)10-8-11(15)12(16)9-13(10)20-3/h8-9H,4-7,16H2,1-3H3,(H,17,19)</inchi>
  <inchikey>TTWJBBZEZQICBI-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Phenol ethers</class>
    <sub_class>Aminophenyl ethers</sub_class>
    <direct_parent>Aminophenyl ethers</direct_parent>
    <alternate_parents>
      <alternative_parent>Alkyl aryl ethers</alternative_parent>
      <alternative_parent>Anisoles</alternative_parent>
      <alternative_parent>Aryl chlorides</alternative_parent>
      <alternative_parent>Carboximidic acids</alternative_parent>
      <alternative_parent>Chlorobenzenes</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Methoxyanilines</alternative_parent>
      <alternative_parent>Methoxybenzenes</alternative_parent>
      <alternative_parent>Organochlorides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Propargyl-type 1,3-dipolar organic compounds</alternative_parent>
      <alternative_parent>Trialkylamines</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Alkyl aryl ether</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminophenyl ether</substituent>
      <substituent>Aniline or substituted anilines</substituent>
      <substituent>Anisole</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Aryl chloride</substituent>
      <substituent>Aryl halide</substituent>
      <substituent>Carboximidic acid</substituent>
      <substituent>Carboximidic acid derivative</substituent>
      <substituent>Chlorobenzene</substituent>
      <substituent>Ether</substituent>
      <substituent>Halobenzene</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Methoxyaniline</substituent>
      <substituent>Methoxybenzene</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Organic 1,3-dipolar compound</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organochloride</substituent>
      <substituent>Organohalogen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Propargyl-type 1,3-dipolar organic compound</substituent>
      <substituent>Tertiary aliphatic amine</substituent>
      <substituent>Tertiary amine</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>benzamides</descriptor>
      <descriptor>monochlorobenzenes</descriptor>
      <descriptor>substituted aniline</descriptor>
      <descriptor>tertiary amino compound</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Metoclopramide - Dopamine Antagonist Action Pathway</name>
      <smpdb_id>SMP0126993</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Metoclopramide Serotonergic Smooth Muscle Contraction</name>
      <smpdb_id>SMP0127039</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Metoclopramide Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0143651</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>1.4</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.18</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.99</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>3.10e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>14.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>299.796</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>299.14005467</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C14H22ClN3O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C14H22ClN3O2/c1-4-18(5-2)7-6-17-14(19)10-8-11(15)12(16)9-13(10)20-3/h8-9H,4-7,16H2,1-3H3,(H,17,19)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>TTWJBBZEZQICBI-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>67.59</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>83.52</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>32.7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>7</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>4</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:0x00007f72826d62c0&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB01233</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>4168</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>4024</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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  </targets>
</compound>
