You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2012-09-06 15:16:52 UTC
Update Date2016-02-11 01:33:48 UTC
HMDB IDHMDB15654
Secondary Accession NumbersNone
Metabolite Identification
Common NameMethacholine
DescriptionMethacholine acts as a non-selective muscarinic receptor agonist to stimulate 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
Thumb
Synonyms
ValueSource
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 FormulaC8H18NO2
Average Molecular Weight160.234
Monoisotopic Molecular Weight160.133753825
IUPAC Name[2-(acetyloxy)propyl]trimethylazanium
Traditional Namemethacholine
CAS Registry Number55-92-5
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 KeyInChIKey=NZWOPGCLSHLLPA-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic nitrogen compounds
Sub ClassOrganonitrogen compounds
Direct ParentTetraalkylammonium salts
Alternative Parents
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
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
BiofunctionNot Available
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
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 DB06709
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06709
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB06709
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID1916
KEGG Compound IDC07471
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethacholine
NuGOwiki LinkHMDB15654
Metagene LinkHMDB15654
METLIN IDNot Available
PubChem Compound1993
PDB IDNot Available
ChEBI ID6804
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 Pi turnover
Gene Name:
CHRM3
Uniprot ID:
P20309
Molecular weight:
66127.4
References
  1. 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. Epub 2010 Oct 1. [20888332 ]
  2. 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. Epub 2010 Mar 25. [20347047 ]
  3. 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. Epub 2009 Nov 27. [19951374 ]
  4. 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. Epub 2009 May 21. [19460789 ]