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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:53 UTC

HMDB ID

HMDB0015154

Secondary Accession Numbers

HMDB15154

Metabolite Identification

Common Name

Bethanechol

Description

Bethanechol 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

COMPND    HMDB0015154
HETATM    1  C1  UNL     1       0.636  -0.617  -1.773  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.812  -0.474  -0.265  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.022   0.636   0.289  1.00  0.00           C  
HETATM    4  N1  UNL     1      -1.427   0.460   0.162  1.00  0.00           N1+
HETATM    5  C4  UNL     1      -1.853  -0.871   0.539  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.970   0.770  -1.124  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.068   1.374   1.123  1.00  0.00           C  
HETATM    8  O1  UNL     1       2.180  -0.107  -0.040  1.00  0.00           O  
HETATM    9  C7  UNL     1       3.046  -0.922   0.674  1.00  0.00           C  
HETATM   10  N2  UNL     1       4.386  -0.490   0.855  1.00  0.00           N  
HETATM   11  O2  UNL     1       2.594  -2.001   1.120  1.00  0.00           O  
HETATM   12  H1  UNL     1      -0.037  -1.450  -2.002  1.00  0.00           H  
HETATM   13  H2  UNL     1       1.620  -0.878  -2.256  1.00  0.00           H  
HETATM   14  H3  UNL     1       0.343   0.348  -2.233  1.00  0.00           H  
HETATM   15  H4  UNL     1       0.661  -1.441   0.214  1.00  0.00           H  
HETATM   16  H5  UNL     1       0.224   0.741   1.361  1.00  0.00           H  
HETATM   17  H6  UNL     1       0.287   1.583  -0.197  1.00  0.00           H  
HETATM   18  H7  UNL     1      -1.364  -1.672  -0.015  1.00  0.00           H  
HETATM   19  H8  UNL     1      -2.952  -0.951   0.304  1.00  0.00           H  
HETATM   20  H9  UNL     1      -1.743  -1.021   1.629  1.00  0.00           H  
HETATM   21  H10 UNL     1      -1.514   1.704  -1.546  1.00  0.00           H  
HETATM   22  H11 UNL     1      -1.988  -0.063  -1.836  1.00  0.00           H  
HETATM   23  H12 UNL     1      -3.053   1.050  -0.961  1.00  0.00           H  
HETATM   24  H13 UNL     1      -3.042   1.731   0.752  1.00  0.00           H  
HETATM   25  H14 UNL     1      -1.429   2.297   1.248  1.00  0.00           H  
HETATM   26  H15 UNL     1      -2.118   0.917   2.134  1.00  0.00           H  
HETATM   27  H16 UNL     1       4.777  -0.321   1.804  1.00  0.00           H  
HETATM   28  H17 UNL     1       5.014  -0.331   0.040  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    8   15
CONECT    3    4   16   17
CONECT    4    5    6    7
CONECT    5   18   19   20
CONECT    6   21   22   23
CONECT    7   24   25   26
CONECT    8    9
CONECT    9   10   11   11
CONECT   10   27   28
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2-Hydroxypropyl)trimethylammonium carbamate	ChEBI
2-(Carbamoyloxy)-N,N,N-trimethylpropan-1-aminium	ChEBI
2-Carbamoyloxypropyl-trimethylazanium	ChEBI
Amidopropyldimethylbetaine	ChEBI
Carbamoyl-beta-methylcholine	ChEBI
Carbamyl-beta-methylcholine	ChEBI
(2-Hydroxypropyl)trimethylammonium carbamic acid	Generator
Carbamoyl-b-methylcholine	Generator
Carbamoyl-β-methylcholine	Generator
Carbamyl-b-methylcholine	Generator
Carbamyl-β-methylcholine	Generator
Besacholine	HMDB
beta-Methyl carbachol chloride	HMDB
Bethaine choline chloride	HMDB
Bethanechol chloride	HMDB
BTC	HMDB
Carbamylmethylcholine chloride	HMDB
Chloride, bethanechol	HMDB
Organon brand OF bethanechol chloride	HMDB
PMSBethanechol chloride	HMDB
Duvoid	HMDB
Hermes, myo	HMDB
Myo hermes	HMDB
Myotonachol	HMDB
Roberts brand OF bethanechol chloride	HMDB
Glenwood brand OF bethanechol chloride	HMDB
Hamilton brand OF bethanechol chloride	HMDB
PMS-Bethanechol chloride	HMDB
Pharmascience brand OF bethanechol chloride	HMDB
Urocarb	HMDB
Bethanecol	HMDB
Myocholine	HMDB
Myotonine	HMDB
PMS Bethanechol chloride	HMDB
Urecholine	HMDB

Chemical Formula

C₇H₁₇N₂O₂

Average Molecular Weight

161.2221

Monoisotopic Molecular Weight

161.129002798

IUPAC Name

1-(trimethylazaniumyl)propan-2-yl carbamate

Traditional Name

bethanechol

CAS Registry Number

674-38-4

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 Key

NZUPCNDJBJXXRF-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.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Quaternary ammonium salts

Direct Parent

Tetraalkylammonium 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 Framework

Aliphatic acyclic compounds

External Descriptors

carbamate ester (CHEBI:3084 )
quaternary ammonium ion (CHEBI:3084 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015154)

Source

Exogenous

Exogenous (HMDB: HMDB0015154)

Process

Not Available

Role

Industrial application

Muscarinic agonist (HMDB: HMDB0015154)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	217 - 221 °C (chloride salt)	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.31 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.31 g/L	ALOGPS
logP	-2.8	ALOGPS
logP	-4.1	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	15.34	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	52.32 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	54.44 m³·mol⁻¹	ChemAxon
Polarizability	17.73 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	137.224	31661259
DarkChem	[M-H]-	133.91	31661259
DeepCCS	[M+H]+	136.553	30932474
DeepCCS	[M-H]-	133.836	30932474
DeepCCS	[M-2H]-	169.931	30932474
DeepCCS	[M+Na]+	145.312	30932474
AllCCS	[M+H]+	135.8	32859911
AllCCS	[M+H-H2O]+	132.1	32859911
AllCCS	[M+NH4]+	139.2	32859911
AllCCS	[M+Na]+	140.1	32859911
AllCCS	[M-H]-	146.4	32859911
AllCCS	[M+Na-2H]-	148.3	32859911
AllCCS	[M+HCOO]-	150.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bethanechol	CC(C[N+](C)(C)C)OC(N)=O	1978.4	Standard polar	33892256
Bethanechol	CC(C[N+](C)(C)C)OC(N)=O	1070.7	Standard non polar	33892256
Bethanechol	CC(C[N+](C)(C)C)OC(N)=O	1214.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Bethanechol,1TMS,isomer #1	CC(C[N+](C)(C)C)OC(=O)N[Si](C)(C)C	1304.7	Semi standard non polar	33892256
Bethanechol,1TMS,isomer #1	CC(C[N+](C)(C)C)OC(=O)N[Si](C)(C)C	1302.9	Standard non polar	33892256
Bethanechol,1TMS,isomer #1	CC(C[N+](C)(C)C)OC(=O)N[Si](C)(C)C	1587.0	Standard polar	33892256
Bethanechol,2TMS,isomer #1	CC(C[N+](C)(C)C)OC(=O)N([Si](C)(C)C)[Si](C)(C)C	1402.9	Semi standard non polar	33892256
Bethanechol,2TMS,isomer #1	CC(C[N+](C)(C)C)OC(=O)N([Si](C)(C)C)[Si](C)(C)C	1438.1	Standard non polar	33892256
Bethanechol,2TMS,isomer #1	CC(C[N+](C)(C)C)OC(=O)N([Si](C)(C)C)[Si](C)(C)C	1556.9	Standard polar	33892256
Bethanechol,1TBDMS,isomer #1	CC(C[N+](C)(C)C)OC(=O)N[Si](C)(C)C(C)(C)C	1534.8	Semi standard non polar	33892256
Bethanechol,1TBDMS,isomer #1	CC(C[N+](C)(C)C)OC(=O)N[Si](C)(C)C(C)(C)C	1531.6	Standard non polar	33892256
Bethanechol,1TBDMS,isomer #1	CC(C[N+](C)(C)C)OC(=O)N[Si](C)(C)C(C)(C)C	1705.1	Standard polar	33892256
Bethanechol,2TBDMS,isomer #1	CC(C[N+](C)(C)C)OC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1856.8	Semi standard non polar	33892256
Bethanechol,2TBDMS,isomer #1	CC(C[N+](C)(C)C)OC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1851.3	Standard non polar	33892256
Bethanechol,2TBDMS,isomer #1	CC(C[N+](C)(C)C)OC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	1744.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Bethanechol GC-MS (Non-derivatized) - 70eV, Positive	splash10-05fu-9200000000-ce89fb005ab6417b9823	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bethanechol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bethanechol 10V, Positive-QTOF	splash10-03di-3900000000-3dba79e269dc8a5a9906	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bethanechol 20V, Positive-QTOF	splash10-0w2a-7900000000-5938fdfa6269132e896a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bethanechol 40V, Positive-QTOF	splash10-0h2g-9300000000-a630235eb0d4cfee2ba0	2017-09-01	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01019	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01019	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01019

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2280

KEGG Compound ID

C06850

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bethanechol

METLIN ID

Not Available

PubChem Compound

2370

PDB ID

Not Available

ChEBI ID

3084

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Muscarinic acetylcholine receptor M2

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

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 ]
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 ]
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 ]
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 ]
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 ]

Showing metabocard for Bethanechol (HMDB0015154)

MOL for HMDB0015154 (Bethanechol)

3D MOL for HMDB0015154 (Bethanechol)

3D SDF for HMDB0015154 (Bethanechol)

3D-SDF for HMDB0015154 (Bethanechol)

PDB for HMDB0015154 (Bethanechol)

3D PDB for HMDB0015154 (Bethanechol)

SMILES for HMDB0015154 (Bethanechol)

INCHI for HMDB0015154 (Bethanechol)

Structure for HMDB0015154 (Bethanechol)

3D Structure for HMDB0015154 (Bethanechol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References