| Common Name |
Methacholine
| Description |
Methacholine acts as a non-selective muscarinic receptor agonist to stimliate the parasympathetic nervous system. It is most commonly used for diagnosing bronchial hyperreactivity, using the bronchial challenge test. Through this test, the drug causes bronchoconstriction and people with pre-existing airway hyperreactivity, such as asthmatics, will react to lower doses of drug.
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
Acetyl-beta-methylcholineChEBI
AcetylmethylcholineChEBI
MChChEBI
Acetyl-b-methylcholineGenerator
Acetyl-β-methylcholineGenerator
Acetyl-beta-methacholine chlorideMeSH
Methacholine chlorideMeSH
Roche brand OF methacholine chlorideMeSH
Acetyl 2 methylcholine chlorideMeSH
Acetyl beta methacholine chlorideMeSH
Acetyl-2-methylcholine chlorideMeSH
Methapharma brand OF methacholine chlorideMeSH
ProvokitMeSH
2-(Acetyloxy)-N,N,N-trimethyl-1-propanaminium chlorideMeSH
Chloride, methacholineMeSH
Lindopharm brand OF methacholine chlorideMeSH
Acetyl beta methylcholineMeSH
MecholineMeSH
MecholylMeSH
ProvocholineMeSH
| Chemical Formlia |
C8H18NO2
| Average Molecliar Weight |
160.234
| Monoisotopic Molecliar Weight |
160.133753825
| IUPAC Name |
[2-(acetyloxy)propyl]trimethylazanium
| Traditional Name |
methacholine
| CAS Registry Number |
55-92-5
| SMILES |
CC(C[N+](C)(C)C)OC(C)=O
| InChI Identifier |
InChI=1S/C8H18NO2/c1-7(11-8(2)10)6-9(3,4)5/h7H,6H2,1-5H3/q+1
| InChI Key |
NZWOPGCLSHLLPA-UHFFFAOYSA-N
| Chemical Taxonomy |
| Description |
This 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.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Organic nitrogen compounds
| Sub Class |
Organonitrogen compounds
| Direct Parent |
Tetraalkylammonium salts
| Alternative Parents |
Carboxylic acid esters
Monocarboxylic acids and derivatives
Organopnictogen compounds
Organic salts
Organic oxides
Hydrocarbon derivatives
Carbonyl compounds
Amines
Organic cations
| Substituents |
Tetraalkylammonium salt
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic salt
Organooxygen compound
Carbonyl group
Amine
Organic cation
Aliphatic acyclic compound
| Molecliar Framework |
Aliphatic acyclic compounds
| External Descriptors |
quaternary ammonium ion (CHEBI:6804 )
acetate ester (CHEBI:6804 )
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Drug
| Biofunction |
Not Available
| Application |
Pharmaceutical
| Cellliar locations |
Membrane
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.068 mg/mLALOGPS
logP-2.7ALOGPS
logP-3.8ChemAxon
logS-3.5ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity55.76 m3·mol-1ChemAxon
Polarizability18.43 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
Not Available
| Biological Properties |
| Cellliar Locations |
Membrane
| Biofluid Locations |
Blood
Urine
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06709
21059682
details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06709
21059682
details
|
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
DB06709
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
Not Available
| KNApSAcK ID |
Not Available
| Chemspider ID |
1916
| KEGG Compound ID |
C07471
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Methacholine
| NuGOwiki Link |
HMDB15654
| Metagene Link |
HMDB15654
| METLIN ID |
Not Available
| PubChem Compound |
1993
| PDB ID |
Not Available
| ChEBI ID |
6804
Product: Paroxetine (hydrochloride)
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
Not 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 Pi turnover
- Gene Name:
- CHRM3
- Uniprot ID:
- P20309
- Molecular weight:
- 66127.4
References
- Liu PS, Chen YY, Feng CK, Lin YH, Yu TC: Muscarinic acetylcholine receptors present in human osteoblast and bone tissue. Eur J Pharmacol. 2011 Jan 10;650(1):34-40. doi: 10.1016/j.ejphar.2010.09.031. Epub 2010 Oct 1. [PubMed:20888332 ]
- Fernandez-Rodriguez S, Broadley KJ, Ford WR, Kidd EJ: Increased muscarinic receptor activity of airway smooth muscle isolated from a mouse model of allergic asthma. Pulm Pharmacol Ther. 2010 Aug;23(4):300-7. doi: 10.1016/j.pupt.2010.03.001. Epub 2010 Mar 25. [PubMed:20347047 ]
- Liu T, Xie C, Chen X, Zhao F, Liu AM, Cho DB, Chong J, Yang PC: Role of muscarinic receptor activation in regulating immune cell activity in nasal mucosa. Allergy. 2010 Aug;65(8):969-77. doi: 10.1111/j.1398-9995.2009.02281.x. Epub 2009 Nov 27. [PubMed:19951374 ]
- Gosens R, Rieks D, Meurs H, Ninaber DK, Rabe KF, Nanninga J, Kolahian S, Halayko AJ, Hiemstra PS, Zuyderduyn S: Muscarinic M3 receptor stimulation increases cigarette smoke-induced IL-8 secretion by human airway smooth muscle cells. Eur Respir J. 2009 Dec;34(6):1436-43. doi: 10.1183/09031936.00045209. Epub 2009 May 21. [PubMed:19460789 ]
PMID: 15203132
