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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4) Show 4 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:39 UTC

HMDB ID

HMDB0014555

Secondary Accession Numbers

HMDB14555

Metabolite Identification

Common Name

Carbachol

Description

Carbachol, also known as miostat or carbastat, belongs to the class of organic compounds known as carbamate esters. Carbamate esters are compounds containing an ester of carbamic acid with the general structure R2NC(=O)OR' (R' not H). They are esters of carbamic acids. Carbachol is an extremely weak acidic (essentially neutral) compound (based on its pKa). Carbachol is a potentially toxic compound. 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. Carbachol 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.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Miostat	HMDB
Carbastat	HMDB
Carbocholine	MeSH
Carboptic	MeSH
Carbamoylcholine	MeSH
Carbachol, isopto	MeSH
Isopto carbachol	MeSH
Carbacholine	MeSH
Carbamann	MeSH
Jestryl	MeSH
Doryl	MeSH
Carbachol	ChEMBL, MeSH
Carbamylcholine	MeSH

Chemical Formula

C₆H₁₅N₂O₂

Average Molecular Weight

147.1955

Monoisotopic Molecular Weight

147.113352734

IUPAC Name

2-(trimethylazaniumyl)ethyl carbamate

Traditional Name

lentine

CAS Registry Number

51-83-2

SMILES

C[N+](C)(C)CCOC(N)=O

InChI Identifier

InChI=1S/C6H14N2O2/c1-8(2,3)4-5-10-6(7)9/h4-5H2,1-3H3,(H-,7,9)/p+1

InChI Key

VPJXQGSRWJZDOB-UHFFFAOYSA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carbamate esters. Carbamate esters are compounds containing an ester of carbamic acid with the general structure R2NC(=O)OR' (R' not H). They are esters of carbamic acids.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Carbamate esters

Alternative Parents

Substituents

Quaternary ammonium salt
Carbamic acid ester
Tetraalkylammonium salt
Carbonic acid derivative
Amine
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organic salt
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic cation
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014555)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	210 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.95 g/L	Not Available
LogP	-3.78	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.95 g/L	ALOGPS
logP	-3	ALOGPS
logP	-4.6	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	15.23	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	50.02 m³·mol⁻¹	ChemAxon
Polarizability	16.08 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]+	132.724	31661259
DarkChem	[M-H]-	125.312	31661259
DeepCCS	[M+H]+	132.033	30932474
DeepCCS	[M-H]-	129.651	30932474
DeepCCS	[M-2H]-	165.385	30932474
DeepCCS	[M+Na]+	140.553	30932474
AllCCS	[M+H]+	131.6	32859911
AllCCS	[M+H-H2O]+	127.8	32859911
AllCCS	[M+NH4]+	135.1	32859911
AllCCS	[M+Na]+	136.1	32859911
AllCCS	[M-H]-	142.8	32859911
AllCCS	[M+Na-2H]-	144.9	32859911
AllCCS	[M+HCOO]-	147.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Carbachol	C[N+](C)(C)CCOC(N)=O	1957.9	Standard polar	33892256
Carbachol	C[N+](C)(C)CCOC(N)=O	1052.3	Standard non polar	33892256
Carbachol	C[N+](C)(C)CCOC(N)=O	1225.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Carbachol,1TMS,isomer #1	C[N+](C)(C)CCOC(=O)N[Si](C)(C)C	1322.3	Semi standard non polar	33892256
Carbachol,1TMS,isomer #1	C[N+](C)(C)CCOC(=O)N[Si](C)(C)C	1308.4	Standard non polar	33892256
Carbachol,1TMS,isomer #1	C[N+](C)(C)CCOC(=O)N[Si](C)(C)C	1580.8	Standard polar	33892256
Carbachol,2TMS,isomer #1	C[N+](C)(C)CCOC(=O)N([Si](C)(C)C)[Si](C)(C)C	1419.8	Semi standard non polar	33892256
Carbachol,2TMS,isomer #1	C[N+](C)(C)CCOC(=O)N([Si](C)(C)C)[Si](C)(C)C	1419.2	Standard non polar	33892256
Carbachol,2TMS,isomer #1	C[N+](C)(C)CCOC(=O)N([Si](C)(C)C)[Si](C)(C)C	1505.3	Standard polar	33892256
Carbachol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)OCC[N+](C)(C)C	1544.1	Semi standard non polar	33892256
Carbachol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)OCC[N+](C)(C)C	1522.5	Standard non polar	33892256
Carbachol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)OCC[N+](C)(C)C	1687.3	Standard polar	33892256
Carbachol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)OCC[N+](C)(C)C)[Si](C)(C)C(C)(C)C	1841.1	Semi standard non polar	33892256
Carbachol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)OCC[N+](C)(C)C)[Si](C)(C)C(C)(C)C	1850.9	Standard non polar	33892256
Carbachol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)OCC[N+](C)(C)C)[Si](C)(C)C(C)(C)C	1688.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Carbachol 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 - Carbachol 10V, Positive-QTOF	splash10-0002-3900000000-152e1eeb42e760a5302f	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbachol 20V, Positive-QTOF	splash10-01p5-9400000000-c6a000b4a0f0d81fef83	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbachol 40V, Positive-QTOF	splash10-01ox-9000000000-193d125ef600d3c64093	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbachol 10V, Positive-QTOF	splash10-01q1-9200000000-f18a0c7a14c29af72a56	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbachol 20V, Positive-QTOF	splash10-03du-9000000000-523aec251c0842a0de1b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Carbachol 40V, Positive-QTOF	splash10-01ow-9000000000-aca9ef45c4530c483eb3	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	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 DB00411	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00411	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Carbachol

METLIN ID

Not Available

PubChem Compound

2551

PDB ID

Not Available

ChEBI ID

Not Available

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. Cytosolic phospholipase A2

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.
Gene Name:: PLA2G4A
Uniprot ID:: P47712
Molecular weight:: 85210.19

References

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. [PubMed:1417779 ]
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. [PubMed:6091414 ]
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. [PubMed:1373616 ]
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. [PubMed:8344290 ]
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. [PubMed:2519894 ]
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. [PubMed:7730640 ]
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. [PubMed:1636494 ]

Enzyme Details

2. Muscarinic acetylcholine receptor M1

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
Gene Name:: CHRM1
Uniprot ID:: P11229
Molecular weight:: 51420.4

References

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. [PubMed:15059034 ]

Enzyme Details

3. 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

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. [PubMed:15485827 ]
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. [PubMed:15333678 ]
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. [PubMed:12948933 ]
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. [PubMed:12505062 ]
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. [PubMed:16181410 ]

Enzyme Details

4. Neuronal acetylcholine receptor subunit alpha-2

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
Gene Name:: CHRNA2
Uniprot ID:: Q15822
Molecular weight:: 59764.8

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 ]
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. doi: 10.1073/pnas.1004956107. Epub 2010 May 24. [PubMed:20498043 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Carbachol (HMDB0014555)

MOL for HMDB0014555 (Carbachol)

3D MOL for HMDB0014555 (Carbachol)

3D SDF for HMDB0014555 (Carbachol)

3D-SDF for HMDB0014555 (Carbachol)

PDB for HMDB0014555 (Carbachol)

3D PDB for HMDB0014555 (Carbachol)

SMILES for HMDB0014555 (Carbachol)

INCHI for HMDB0014555 (Carbachol)

Structure for HMDB0014555 (Carbachol)

3D Structure for HMDB0014555 (Carbachol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References

References

References