Methacholine (CED0002462)

Record Information
Version1.0
Creation Date2016-05-25 18:29:55 UTC
Update Date2026-08-24 18:01:22 UTC
Accession NumberCHEM022361
Identification
Common NameMethacholine
ClassSmall Molecule
Description
Methacholine is an organic compound with the chemical formula C8H18NO2 and an average molecular weight of 160.23 g/mol. Methacholine belongs to the quaternary ammonium salts, a subclass of organonitrogen compounds within the organic compounds. This compound is associated with nine recorded sources, including electrical and electronic equipment such as electrodes, conductive bodies characterized by conductive materials, and electrically stimulated smoking devices. It is also found in household cleaning and consumer products, specifically pipe accessories, tobacco smoke filters, and non-electric simulated smoking devices. Additionally, it is identified in food preservation within food, food processing and cookware, in indoor air via air, dust and atmospheric transport, and as unclassified diagnostic agents within healthcare, pharmaceuticals and veterinary products. The recorded routes of exposure for methacholine are respiratory and inhalation. In terms of biological activity, methacholine interacts with five recorded protein targets. It acts as an agonist for the muscarinic acetylcholine receptors M1 (CHRM1), M2 (CHRM2), M3 (CHRM3), and M4 (CHRM4), as well as one other protein.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
Acetyl-beta-methylcholineChEBI
AcetylmethylcholineChEBI
MChChEBI
Acetyl-b-methylcholineGenerator
Acetyl-β-methylcholineGenerator
Acetyl-beta-methacholine chlorideHMDB
Methacholine chlorideHMDB
Roche brand OF methacholine chlorideHMDB
Acetyl 2 methylcholine chlorideHMDB
Acetyl beta methacholine chlorideHMDB
Acetyl-2-methylcholine chlorideHMDB
Methapharma brand OF methacholine chlorideHMDB
ProvokitHMDB
2-(Acetyloxy)-N,N,N-trimethyl-1-propanaminium chlorideHMDB
Chloride, methacholineHMDB
Lindopharm brand OF methacholine chlorideHMDB
Acetyl beta methylcholineHMDB
MecholineHMDB
MecholylHMDB
ProvocholineHMDB
Chemical FormulaC8H18NO2
Average Molecular Mass160.234 g/mol
Monoisotopic Mass160.134 g/mol
CAS Registry Number55-92-5
IUPAC Name[2-(acetyloxy)propyl]trimethylazanium
Traditional Namemethacholine
SMILESCC(C[N+](C)(C)C)OC(C)=O
InChI IdentifierInChI=1S/C8H18NO2/c1-7(11-8(2)10)6-9(3,4)5/h7H,6H2,1-5H3/q+1
InChI KeyNZWOPGCLSHLLPA-UHFFFAOYSA-N
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
  • 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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.068 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity55.76 m³·mol⁻¹ChemAxon
Polarizability18.43 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0pb9-9300000000-58ac206c8375cdba4dbeNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-1900000000-6dcde9ec782ba8c520edNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0j4i-4900000000-0fae01014a0c2794d4f4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udj-9600000000-bcea3e3a42888cb235a2Not AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
1034.0Log mg/kg[580:1800]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
19Indoor airAir, dust & atmospheric transportNot Available
233BrushesPersonal care & cosmeticsNot Available
411Unclassified diagnostic agentsHealthcare, pharmaceuticals & veterinary productsNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
596AcaricidesAgriculture & land managementNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
Pathways
4 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Muscarinic acetylcholine receptor M4 structureClick to view 3D structureMuscarinic acetylcholine receptor M4P08173HumansPredicted (SEA)13.8572
Muscarinic acetylcholine receptor M2 structureClick to view 3D structureMuscarinic acetylcholine receptor M2P08172HumansPredicted (SEA)17.6718
Click to view 3D structureMuscarinic acetylcholine receptor M1P08482Rattus norvegicusPredicted (SEA)13.8572
Click to view 3D structureMuscarinic acetylcholine receptor M2P10980Rattus norvegicusPredicted (SEA)13.7015
Click to view 3D structureMuscarinic acetylcholine receptor M4P08485Rattus norvegicusPredicted (SEA)3.58106
Click to view 3D structureMuscarinic acetylcholine receptor M3P08483Rattus norvegicusPredicted (SEA)4.9045
Click to view 3D structureMitochondrial carnitine/acylcarnitine carrier proteinO43772HumansPredicted (SEA)2.02408
Muscarinic acetylcholine receptor M1 structureClick to view 3D structureMuscarinic acetylcholine receptor M1P11229HumansPredicted (SEA)358.807
Muscarinic acetylcholine receptor M3 structureClick to view 3D structureMuscarinic acetylcholine receptor M3P20309HumansPredicted (SEA)262.352
Muscarinic acetylcholine receptor M5 structureClick to view 3D structureMuscarinic acetylcholine receptor M5P08912HumansPredicted (SEA)295.516
Click to view 3D structureCarnitine O-palmitoyltransferase 2, mitochondrialP23786HumansPredicted (SEA)93.4969
Click to view 3D structureShort transient receptor potential channel 4Q9QUQ5Mus musculusPredicted (SEA)1437.02
Click to view 3D structure1-deoxy-D-xylulose-5-phosphate synthaseB7UJP3Escherichia coli O127:H6 (strain E2348/69 / EPEC)Predicted (SEA)4.82665
Click to view 3D structureArabinose 5-phosphate isomerase KdsDQ5NGP7Francisella tularensis subsp. tularensis (strain SCHU S4 / Schu 4)Predicted (SEA)1.40129
Click to view 3D structure6-phosphogluconate dehydrogenase, decarboxylatingP00349Ovis ariesPredicted (SEA)3.03612
Aminopeptidase N structureClick to view 3D structureAminopeptidase NP04825Escherichia coli (strain K12)Predicted (SEA)15.1806
Click to view 3D structureMuscarinic acetylcholine receptor M3Q8VH26Cavia porcellusPredicted (SEA)1374.04
Click to view 3D structureAcetylcholinesteraseP21836Mus musculusPredicted (SEA)2642.28
72 kDa type IV collagenase structureClick to view 3D structure72 kDa type IV collagenaseP08253HumansPredicted (SEA)6314.19
Matrix metalloproteinase-9 structureClick to view 3D structureMatrix metalloproteinase-9P14780HumansPredicted (SEA)5837.91
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)5900.5
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)5973.84
Matrix metalloproteinase-14 structureClick to view 3D structureMatrix metalloproteinase-14P50281HumansPredicted (SEA)5568.63
Carnitine O-palmitoyltransferase 1, liver isoform structureClick to view 3D structureCarnitine O-palmitoyltransferase 1, liver isoformP50416HumansPredicted (SEA)2955.39
Interstitial collagenase structureClick to view 3D structureInterstitial collagenaseP03956HumansPredicted (SEA)6104.31
Concentrations
Not Available
External Links
DrugBank IDDB06709
HMDB IDHMDB0015654
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMethacholine
Chemspider ID1916
ChEBI ID6804
PubChem Compound ID1993
Kegg Compound IDC07471
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12128066
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15275856
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=15694846
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=16477439
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=18775882
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=19589828
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22826043
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22981792
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23429803
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=8124805
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=8420242