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Record Information
Creation Date2012-09-06 15:16:49 UTC
Update Date2017-03-02 21:33:17 UTC
Secondary Accession NumbersNone
Metabolite Identification
Common NameCarbachol
DescriptionCarbachol is only found in individuals that have used or taken this drug. It is a slowly hydrolyzed cholinergic agonist that acts at both muscarinic and nicotinic receptors. [PubChem]Carbachol is a parasympathomimetic that stimulates both muscarinic and nicotinic receptors. In topical ocular and intraocular administration its principal effects are miosis and increased aqueous humour outflow.
(2-Carbamoyloxyethyl)trimethylammonium chlorideChEBI
(2-Hydroxyethyl)trimethyl ammonium chloride carbamateChEBI
(2-Hydroxyethyl)trimethylammonium chloride carbamateChEBI
2-((Aminocarbonyl)oxy)-N,N,N-trimethylethanaminium chlorideChEBI
2-((Aminocarbonyl)oxy)-N,N,N-trimethylethanaminum chlorideChEBI
Carbachol chlorideChEBI
Choline carbamate chlorideChEBI
Choline chloride, carbamateChEBI
Choline chlorine carbamateChEBI
Karbamoylcholin chloridChEBI
(2-Hydroxyethyl)trimethyl ammonium chloride carbamic acidGenerator
(2-Hydroxyethyl)trimethylammonium chloride carbamic acidGenerator
Choline carbamic acid chlorideGenerator
Choline chloride, carbamic acidGenerator
Choline chlorine carbamic acidGenerator
Carbachol, isoptoMeSH
isopto CarbacholMeSH
Chemical FormulaC6H15ClN2O2
Average Molecular Weight182.649
Monoisotopic Molecular Weight182.082205441
IUPAC Name2-(trimethylazaniumyl)ethyl carbamate chloride
Traditional Namelentine chloride
CAS Registry Number51-83-2
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as tetraalkylammonium salts. These are organonitrogen compounds containing a quaternary ammonium substituted with four alkyl chains.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic nitrogen compounds
Sub ClassOrganonitrogen compounds
Direct ParentTetraalkylammonium salts
Alternative Parents
  • Tetraalkylammonium salt
  • Carboximidic acid derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Hydrochloride
  • Organic salt
  • Organic zwitterion
  • Organooxygen compound
  • Imine
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
StatusExpected but not Quantified
  • Drug
  • Analgesics, Non-Narcotic
  • Cardiotonic Agents
  • Cholinergic Agonists
  • Miotics
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
Experimental Properties
Melting Point210 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility9.48e-01 g/LNot Available
LogP-3.78Not Available
Predicted Properties
Water Solubility0.95 mg/mLALOGPS
pKa (Strongest Acidic)15.23ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area52.32 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity50.02 m3·mol-1ChemAxon
Polarizability16.02 Å3ChemAxon
Number of Rings0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00411
  • Not Applicable
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00411
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00411
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5626
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCarbachol
NuGOwiki LinkHMDB14555
Metagene LinkHMDB14555
METLIN IDNot Available
PubChem Compound5831
PDB IDNot Available
ChEBI ID3385
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available


General function:
Involved in metabolic process
Specific function:
Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory response.
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  1. Konrad RJ, Jolly YC, Major C, Wolf BA: Carbachol stimulation of phospholipase A2 and insulin secretion in pancreatic islets. Biochem J. 1992 Oct 1;287 ( Pt 1):283-90. [1417779 ]
  2. Enyedi P, Fredholm BB: Calcium-dependent enhancement by carbachol of the VIP-induced cyclic AMP accumulation in cat submandibular gland. Acta Physiol Scand. 1984 Apr;120(4):523-8. [6091414 ]
  3. Grosfils K, Gomez F, Dehaye JP: Inhibition by mepacrine and amylase secretion from intact and permeabilized rat pancreatic acini. Biochem Biophys Res Commun. 1992 Apr 15;184(1):408-13. [1373616 ]
  4. Ying Z, Tojo H, Nonaka Y, Okamoto M: Cloning and expression of phospholipase A2 from guinea pig gastric mucosa, its induction by carbachol and secretion in vivo. Eur J Biochem. 1993 Jul 1;215(1):91-7. [8344290 ]
  5. Strosznajder J, Strosznajder RP: Guanine nucleotides and fluoride enhance carbachol-mediated arachidonic acid release from phosphatidylinositol. Evidence for involvement of GTP-binding protein in phospholipase A2 activation. J Lipid Mediat. 1989 Jul-Aug;1(4):217-29. [2519894 ]
  6. Hirasawa N, Santini F, Beaven MA: Activation of the mitogen-activated protein kinase/cytosolic phospholipase A2 pathway in a rat mast cell line. Indications of different pathways for release of arachidonic acid and secretory granules. J Immunol. 1995 May 15;154(10):5391-402. [7730640 ]
  7. Strosznajder J, Samochocki M: Carbachol-stimulated release of arachidonic acid and eicosanoids from brain cortex synaptoneurosome lipids of adult and aged rats. Adv Exp Med Biol. 1992;318:251-8. [1636494 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
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  1. Weiner DM, Goodman MW, Colpitts TM, Feddock MA, Duggento KL, Nash NR, Levey AI, Brann MR: Functional screening of drug target genes: m1 muscarinic acetylcholine receptor phenotypes in degenerative dementias. Am J Pharmacogenomics. 2004;4(2):119-28. [15059034 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition
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  1. Peter JC, Wallukat G, Tugler J, Maurice D, Roegel JC, Briand JP, Hoebeke J: Modulation of the M2 muscarinic acetylcholine receptor activity with monoclonal anti-M2 receptor antibody fragments. J Biol Chem. 2004 Dec 31;279(53):55697-706. Epub 2004 Oct 14. [15485827 ]
  2. May LT, Lin Y, Sexton PM, Christopoulos A: Regulation of M2 muscarinic acetylcholine receptor expression and signaling by prolonged exposure to allosteric modulators. J Pharmacol Exp Ther. 2005 Jan;312(1):382-90. Epub 2004 Aug 27. [15333678 ]
  3. Sawatzky DA, Kingham PJ, Durcan N, McLean WG, Costello RW: Eosinophil-induced release of acetylcholine from differentiated cholinergic nerve cells. Am J Physiol Lung Cell Mol Physiol. 2003 Dec;285(6):L1296-304. Epub 2003 Aug 29. [12948933 ]
  4. Sterin-Borda L, Joensen L, Bayo-Hanza C, Esteva M, Borda E: Therapeutic use of muscarinic acetylcholine receptor peptide to prevent mice chagasic cardiac dysfunction. J Mol Cell Cardiol. 2002 Dec;34(12):1645-54. [12505062 ]
  5. Zuchner T, Schliebs R, Perez-Polo JR: Down-regulation of muscarinic acetylcholine receptor M2 adversely affects the expression of Alzheimer's disease-relevant genes and proteins. J Neurochem. 2005 Oct;95(1):20-32. [16181410 ]
General function:
Involved in extracellular ligand-gated ion channel activity
Specific function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane
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  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
  3. An MC, Lin W, Yang J, Dominguez B, Padgett D, Sugiura Y, Aryal P, Gould TW, Oppenheim RW, Hester ME, Kaspar BK, Ko CP, Lee KF: Acetylcholine negatively regulates development of the neuromuscular junction through distinct cellular mechanisms. Proc Natl Acad Sci U S A. 2010 Jun 8;107(23):10702-7. Epub 2010 May 24. [20498043 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]