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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2021-09-14 15:20:33 UTC
HMDB IDHMDB0015154
Secondary Accession Numbers
  • HMDB15154
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
Data?1582753264
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
Chloride, bethanecholHMDB
Organon brand OF bethanechol chlorideHMDB
PMSBethanechol chlorideHMDB
DuvoidHMDB
Hermes, myoHMDB
Myo hermesHMDB
MyotonacholHMDB
Roberts brand OF bethanechol chlorideHMDB
Glenwood brand OF bethanechol chlorideHMDB
Hamilton brand OF bethanechol chlorideHMDB
PMS-Bethanechol chlorideHMDB
Pharmascience brand OF bethanechol chlorideHMDB
UrocarbHMDB
BethanecolHMDB
MyocholineHMDB
MyotonineHMDB
PMS Bethanechol chlorideHMDB
UrecholineHMDB
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 KeyNZUPCNDJBJXXRF-UHFFFAOYSA-O
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tetraalkylammonium salts. These are organonitrogen compounds containing a quaternary ammonium substituted with four alkyl chains.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassQuaternary ammonium salts
Direct ParentTetraalkylammonium salts
Alternative Parents
Substituents
  • Tetraalkylammonium salt
  • Carboximidic acid derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Imine
  • Amine
  • Organic cation
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point217 - 221 °C (chloride salt)Not Available
Boiling PointNot AvailableNot Available
Water Solubility0.31 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.31 g/LALOGPS
logP10(-2.8) g/LALOGPS
logP10(-4.1) g/LChemAxon
logS10(-2.8) g/LALOGPS
pKa (Strongest Acidic)15.34ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area52.32 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity54.44 m³·mol⁻¹ChemAxon
Polarizability17.73 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+137.22431661259
DarkChem[M-H]-133.9131661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BethanecholCC(C[N+](C)(C)C)OC(N)=O1978.4Standard polar33892256
BethanecholCC(C[N+](C)(C)C)OC(N)=O1070.7Standard non polar33892256
BethanecholCC(C[N+](C)(C)C)OC(N)=O1214.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Bethanechol,1TMS,isomer #1CC(C[N+](C)(C)C)OC(=O)N[Si](C)(C)C1304.7Semi standard non polar33892256
Bethanechol,1TMS,isomer #1CC(C[N+](C)(C)C)OC(=O)N[Si](C)(C)C1302.9Standard non polar33892256
Bethanechol,1TMS,isomer #1CC(C[N+](C)(C)C)OC(=O)N[Si](C)(C)C1587.0Standard polar33892256
Bethanechol,2TMS,isomer #1CC(C[N+](C)(C)C)OC(=O)N([Si](C)(C)C)[Si](C)(C)C1402.9Semi standard non polar33892256
Bethanechol,2TMS,isomer #1CC(C[N+](C)(C)C)OC(=O)N([Si](C)(C)C)[Si](C)(C)C1438.1Standard non polar33892256
Bethanechol,2TMS,isomer #1CC(C[N+](C)(C)C)OC(=O)N([Si](C)(C)C)[Si](C)(C)C1556.9Standard polar33892256
Bethanechol,1TBDMS,isomer #1CC(C[N+](C)(C)C)OC(=O)N[Si](C)(C)C(C)(C)C1534.8Semi standard non polar33892256
Bethanechol,1TBDMS,isomer #1CC(C[N+](C)(C)C)OC(=O)N[Si](C)(C)C(C)(C)C1531.6Standard non polar33892256
Bethanechol,1TBDMS,isomer #1CC(C[N+](C)(C)C)OC(=O)N[Si](C)(C)C(C)(C)C1705.1Standard polar33892256
Bethanechol,2TBDMS,isomer #1CC(C[N+](C)(C)C)OC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1856.8Semi standard non polar33892256
Bethanechol,2TBDMS,isomer #1CC(C[N+](C)(C)C)OC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1851.3Standard non polar33892256
Bethanechol,2TBDMS,isomer #1CC(C[N+](C)(C)C)OC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1744.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Bethanechol GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fu-9200000000-ce89fb005ab6417b98232017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bethanechol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bethanechol 10V, Positive-QTOFsplash10-03di-3900000000-3dba79e269dc8a5a99062017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bethanechol 20V, Positive-QTOFsplash10-0w2a-7900000000-5938fdfa6269132e896a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bethanechol 40V, Positive-QTOFsplash10-0h2g-9300000000-a630235eb0d4cfee2ba02017-09-01Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01019 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01019 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01019
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2280
KEGG Compound IDC06850
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBethanechol
METLIN IDNot Available
PubChem Compound2370
PDB IDNot Available
ChEBI ID3084
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:16953191 ]