<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-25 18:24:11 UTC</creation_date>
  <update_date>2026-08-19 07:19:17 UTC</update_date>
  <accession/>
  <common_name>Rivastigmine</common_name>
  <class>SmallMolecule</class>
  <description>Rivastigmine is an organic compound with the formula C14H22N2O2 and an average molecular weight of 250.34 g/mol. Rivastigmine belongs to the phenoxy compounds, a subclass of benzene and substituted derivatives within the organic compounds. It is categorized within the superclass of benzenoids. This compound acts as an inhibitor of two protein targets: cholinesterase (BCHE) and acetylcholinesterase (ACHE). In terms of health effects, rivastigmine is used as a treatment for Alzheimer's disease (PMC4179059).

The compound is found in or released from 11 recorded sources. Within healthcare, pharmaceuticals, and veterinary products, it is utilized as anti-dementia drugs. Other recorded sources include household cleaning and consumer products, such as soap dispensers, other smoking requisites, and non electric simulated smoking devices. It is also associated with electrical and electronic equipment, including television systems, video games, antennas, amplifiers, and radio transmission systems. Additionally, it is linked to food, food processing, and cookware, specifically the preparation of wine or sparkling wine and the preparation of vinegar. Recorded exposure routes for rivastigmine include transdermal, topical, and oral administration.</description>
  <categories/>
  <types>
    <type>Human Neurotoxin</type>
  </types>
  <synonyms/>
  <chemical_formula>C14H22N2O2</chemical_formula>
  <average_molecular_weight>250.3367</average_molecular_weight>
  <monisotopic_moleculate_weight>250.168127958</monisotopic_moleculate_weight>
  <iupac_name>3-[(1S)-1-(dimethylamino)ethyl]phenyl N-ethyl-N-methylcarbamate</iupac_name>
  <traditional_iupac>exelon</traditional_iupac>
  <cas_registry_number>123441-03-2</cas_registry_number>
  <smiles>CCN(C)C(=O)OC1=CC=CC(=C1)[C@H](C)N(C)C</smiles>
  <inchi>InChI=1S/C14H22N2O2/c1-6-16(5)14(17)18-13-9-7-8-12(10-13)11(2)15(3)4/h7-11H,6H2,1-5H3/t11-/m0/s1</inchi>
  <inchikey>XSVMFMHYUFZWBK-NSHDSACASA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Phenoxy compounds</sub_class>
    <direct_parent>Phenoxy compounds</direct_parent>
    <alternate_parents>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Carbamate esters</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic carbonic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Trialkylamines</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Amine</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Carbamic acid ester</substituent>
      <substituent>Carbonic acid derivative</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Hydrocarbon derivative</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>Phenoxy compound</substituent>
      <substituent>Tertiary aliphatic amine</substituent>
      <substituent>Tertiary amine</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>carbamate ester</descriptor>
      <descriptor>tertiary amino compound</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Rivastigmine Action Pathway (new)</name>
      <smpdb_id>SMP0126688</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Rivastigmine Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0143419</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Rivastigmine Predicted Metabolism Pathway</name>
      <smpdb_id>SMP0174555</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>2.41</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.45</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.09</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>2.04e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.41</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>8.89</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>3-[(1S)-1-(dimethylamino)ethyl]phenyl N-ethyl-N-methylcarbamate</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>250.3367</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>250.168127958</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCN(C)C(=O)OC1=CC=CC(=C1)[C@H](C)N(C)C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C14H22N2O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C14H22N2O2/c1-6-16(5)14(17)18-13-9-7-8-12(10-13)11(2)15(3)4/h7-11H,6H2,1-5H3/t11-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>XSVMFMHYUFZWBK-NSHDSACASA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>32.78</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>73.37</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>28.53</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>0</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:0x00007f7225d90aa0&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB00989</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>77991</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>70377</chemspider_id>
  <kegg_id/>
  <uniprot_id/>
  <omim_id/>
  <chebi_id/>
  <biocyc_id/>
  <ctd_id/>
  <stitch_id/>
  <actor_id/>
  <pdb_id/>
  <wikipidia/>
  <general_references/>
  <targets>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id/>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0000426</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
    <target>
      <target_id>BE0002180</target_id>
      <mechanism_of_action/>
      <constants/>
      <references/>
    </target>
  </targets>
</compound>
