<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2026-03-27 00:28:49 UTC</creation_date>
  <update_date>2026-08-23 07:19:52 UTC</update_date>
  <accession/>
  <common_name>Carbamylcholine</common_name>
  <class>SmallMolecule</class>
  <description>Carbamylcholine is an organic compound with the formula C6H15N2O2 and an average molecular weight of 147.20 g/mol. Carbamylcholine belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds.

This compound is identified as an agonist for five protein targets, including the muscarinic acetylcholine receptors M1 (CHRM1), M2 (CHRM2), and M3 (CHRM3), as well as the neuronal acetylcholine receptor subunit alpha-2 (CHRNA2) and one other protein. Its recorded exposure routes include ophthalmic, intraocular, oral, and subcutaneous administration.

Carbamylcholine is found in or released from 18 recorded sources across several categories. In healthcare, pharmaceuticals, and veterinary products, it is used in miotics, antiglaucoma preparations, and parasympathomimetics. Within the food, food processing, and cookware category, it is associated with food preservation. It is also found in household cleaning and consumer products, specifically in soap detergents, bleaching agents, perfumes within detergents and soaps, tobacco smoke filters, and non-electric simulated smoking devices. Additionally, it is listed in relation to electrical and electronic equipment, including discharge lamps, antennas, conductors or conductive bodies characterised by the conductive materials, electrically stimulated smoking devices, and electric hearing aids, among four other sources. Finally, it is recorded as being present in building and construction materials, specifically ladders.</description>
  <categories/>
  <types>
    <type>Human Neurotoxin</type>
  </types>
  <synonyms>
    <synonym>2-((Aminocarbonyl)oxy)-N,N,N-trimethylethanaminium</synonym>
    <synonym>2-(Carbamoyloxy)-N,N,N-trimethylethanaminium</synonym>
    <synonym>2-aminocarbonyloxyethyl-trimethyl-azanium</synonym>
    <synonym>2-carbamoyloxyethyl-trimethyl-ammonium</synonym>
    <synonym>2-carbamoyloxyethyl-trimethylammonium</synonym>
    <synonym>2-carbamoyloxyethyl-trimethylazanium</synonym>
    <synonym>2-[(AMINOCARBONYL)OXY]-N,N,N-TRIMETHYLETHAMINIUM</synonym>
    <synonym>2-[Hydroxy(imino)methoxy]-N,N,N-trimethylethanaminium</synonym>
    <synonym>BPBio1_001055</synonym>
    <synonym>BSPBio_000959</synonym>
    <synonym>BSPBio_001927</synonym>
    <synonym>Carbachol</synonym>
    <synonym>Carbachol USP27</synonym>
    <synonym>Carbacholin</synonym>
    <synonym>Carbamoylcholine</synonym>
    <synonym>CARBAMYL-CHOLINE</synonym>
    <synonym>Carbamylcholine cation</synonym>
    <synonym>CARBASTAT</synonym>
    <synonym>Carbastat intraocular</synonym>
    <synonym>CarbastatÃ‚Â®</synonym>
    <synonym>Carbocholin</synonym>
    <synonym>Carboptic</synonym>
    <synonym>CarbopticÃ‚Â®</synonym>
    <synonym>CAS-51-83-2</synonym>
    <synonym>CB</synonym>
    <synonym>CCE</synonym>
    <synonym>Choline chlorine carbamate</synonym>
    <synonym>Choline, carbonate (ester)</synonym>
    <synonym>Doryl (pharmaceutical)</synonym>
    <synonym>Ethanaminium, 2-((aminocarbonyl)oxy)-N,N,N-trimethyl-</synonym>
    <synonym>Ethanaminium, 2-(hydroxyiminomethoxy)-N,N,N-trimethyl-</synonym>
    <synonym>Ethanaminium, 2-[(aminocarbonyl)oxy]-N,N,N-trimethyl-</synonym>
    <synonym>IDI1_000725</synonym>
    <synonym>Isopto Carbachol</synonym>
    <synonym>Lentine</synonym>
    <synonym>Lopac0_000243</synonym>
    <synonym>NCGC00163219-01</synonym>
    <synonym>Prestwick2_000880</synonym>
    <synonym>Prestwick3_000880</synonym>
    <synonym>Spectrum5_000934</synonym>
    <synonym>UNII-54Z8M50D6Q</synonym>
    <synonym>UNII:54Z8M50D6Q</synonym>
  </synonyms>
  <chemical_formula>C6H15N2O2</chemical_formula>
  <average_molecular_weight>147.197</average_molecular_weight>
  <monisotopic_moleculate_weight>147.113353</monisotopic_moleculate_weight>
  <iupac_name>2-(trimethylazaniumyl)ethyl carbamate</iupac_name>
  <traditional_iupac>lentine</traditional_iupac>
  <cas_registry_number>462-58-8</cas_registry_number>
  <smiles>C[N+](C)(C)CCOC(N)=O</smiles>
  <inchi>InChI=1S/C6H14N2O2/c1-8(2,3)4-5-10-6(7)9/h4-5H2,1-3H3,(H-,7,9)/p+1</inchi>
  <inchikey>VPJXQGSRWJZDOB-UHFFFAOYSA-O</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>Carbamate esters</direct_parent>
    <alternate_parents>
      <alternative_parent>Amines</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 cations</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic salts</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Tetraalkylammonium salts</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Amine</substituent>
      <substituent>Carbamic acid ester</substituent>
      <substituent>Carbonic acid derivative</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic cation</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic salt</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Quaternary ammonium salt</substituent>
      <substituent>Tetraalkylammonium salt</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <descriptors/>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Carbachol Drug Metabolism Pathway</name>
      <smpdb_id>SMP0145443</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>-4.6</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.95</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-2.41</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>7.06e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>-4.6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>15.23</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>2-(trimethylazaniumyl)ethyl carbamate</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>147.197</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>147.113353</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C[N+](C)(C)CCOC(N)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C6H15N2O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C6H14N2O2/c1-8(2,3)4-5-10-6(7)9/h4-5H2,1-3H3,(H-,7,9)/p+1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>VPJXQGSRWJZDOB-UHFFFAOYSA-O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>52.32</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>50.02</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>16.08</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>4</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>1</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:0x00007f3bb014f5a8&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB00411</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>2551</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>2454</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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</compound>
