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Record Information
Version3.6
Creation Date2012-09-06 15:16:51 UTC
Update Date2016-02-11 01:31:40 UTC
HMDB IDHMDB15154
Secondary Accession NumbersNone
Metabolite Identification
Common NameBethanechol
DescriptionBethanechol is a synthetic ester structurally and pharmacologically related to acetylcholine. A slowly hydrolyzed muscarinic agonist with no nicotinic effects, bethanechol is generally used to increase smooth muscle tone, as in the GI tract following abdominal surgery or in urinary retention in the absence of obstruction. It may cause hypotension, cardiac rate changes, and bronchial spasms. [PubChem]
Structure
Thumb
Synonyms
ValueSource
(2-Hydroxypropyl)trimethylammonium carbamateChEBI
2-(Carbamoyloxy)-N,N,N-trimethylpropan-1-aminiumChEBI
2-Carbamoyloxypropyl-trimethylazaniumChEBI
AmidopropyldimethylbetaineChEBI
Carbamoyl-beta-methylcholineChEBI
Carbamyl-beta-methylcholineChEBI
(2-Hydroxypropyl)trimethylammonium carbamic acidGenerator
Carbamoyl-b-methylcholineGenerator
Carbamoyl-β-methylcholineGenerator
Carbamyl-b-methylcholineGenerator
Carbamyl-β-methylcholineGenerator
BesacholineHMDB
beta-Methyl carbachol chlorideHMDB
Bethaine choline chlorideHMDB
Bethanechol chlorideHMDB
BTCHMDB
Carbamylmethylcholine chlorideHMDB
Chemical FormulaC7H17N2O2
Average Molecular Weight161.2221
Monoisotopic Molecular Weight161.129002798
IUPAC Name1-(trimethylazaniumyl)propan-2-yl carbamate
Traditional Namebethanechol
CAS Registry Number674-38-4
SMILES
CC(C[N+](C)(C)C)OC(N)=O
InChI Identifier
InChI=1S/C7H16N2O2/c1-6(11-7(8)10)5-9(2,3)4/h6H,5H2,1-4H3,(H-,8,10)/p+1
InChI KeyInChIKey=NZUPCNDJBJXXRF-UHFFFAOYSA-O
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cholines. These are organic compounds containing a N,N,N-trimethylethanolammonium cation.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassQuaternary ammonium salts
Sub ClassCholines
Direct ParentCholines
Alternative Parents
Substituents
  • Choline
  • Hydrocarbon derivative
  • Organooxygen compound
  • Amine
  • Organic cation
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Muscarinic Agonists
  • Parasympathomimetics
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point217 - 221 °C (chloride salt)Not Available
Boiling PointNot AvailableNot Available
Water Solubility3.11e-01 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.31 mg/mLALOGPS
logP-2.8ALOGPS
logP-4.1ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)15.34ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area52.32 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity54.44 m3·mol-1ChemAxon
Polarizability17.73 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01019
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01019
  • Not Applicable
details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-6 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-3 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01019
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2280
KEGG Compound IDC06850
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBethanechol
NuGOwiki LinkHMDB15154
Metagene LinkHMDB15154
METLIN IDNot Available
PubChem Compound2370
PDB IDNot Available
ChEBI ID3084
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

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
Gene Name:
CHRM2
Uniprot ID:
P08172
Molecular weight:
51714.6
References
  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. Agrawal A, Hila A, Tutuian R, Mainie I, Castell DO: Bethanechol improves smooth muscle function in patients with severe ineffective esophageal motility. J Clin Gastroenterol. 2007 Apr;41(4):366-70. [17413603 ]
  4. Buranakarl C, Kijtawornrat A, Angkanaporn K, Komolvanich S, Bovee KC: Effects of bethanechol on canine urinary bladder smooth muscle function. Res Vet Sci. 2001 Dec;71(3):175-81. [11798291 ]
  5. Cruzblanca H: An M2-like muscarinic receptor enhances a delayed rectifier K+ current in rat sympathetic neurones. Br J Pharmacol. 2006 Oct;149(4):441-9. Epub 2006 Sep 4. [16953191 ]