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A2251

Sigma-Aldrich

Acetyl-β-methylcholine chloride

≥98% (TLC), powder

Synonym(s):

(2-Acetoxypropyl)trimethylammonium chloride, Methacholine chloride

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About This Item

Linear Formula:
CH3COOCH(CH3)CH2N(Cl)(CH3)3
CAS Number:
62-51-1
Molecular Weight:
195.69
Beilstein/REAXYS Number:
4162373
EC Number:
200-537-2
MDL number:
MFCD00011817
UNSPSC Code:
12352211
PubChem Substance ID:
24277821
NACRES:
NA.25

Quality Level

100

assay

≥98% (TLC)

form

powder

mp

171-173 °C (lit.)

solubility

H2O: 50 mg/mL (solutions undergo rapid, pH-dependent decomposition at pH > 6.)

storage temp.

−20°C

SMILES string

[Cl-].CC(C[N+](C)(C)C)OC(C)=O

InChI

1S/C8H18NO2.ClH/c1-7(11-8(2)10)6-9(3,4)5;/h7H,6H2,1-5H3;1H/q+1;/p-1

InChI key

JHPHVAVFUYTVCL-UHFFFAOYSA-M

Gene Information

human ... CHRM1(1128) , CHRM2(1129) , CHRM3(1131) , CHRM4(1132) , CHRM5(1133)

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Application

Acetyl-β-methylcholine (methacholine), an analog of acetylcholine, is use as a receptor agonist to study processes such as airway hyperresponsiveness associated with asthma.

Biochem/physiol Actions

Metabolically stable analog of acetylcholine; muscarinic agonist. Its ability to constrict airway smooth muscle is used to assess bronchial reactivity in the laboratory and clinically.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Mina Youssef et al.
The Journal of pharmacology and experimental therapeutics, 373(3), 476-487 (2020-04-11)
Zona pellucida binding protein 2 (Zpbp2) and ORMDL sphingolipid biosynthesis regulator 3 (Ormdl3), mapped downstream of Zpbp2, were identified as two genes associated with airway hyper-responsiveness (AHR). Ormdl3 gene product has been shown to regulate the biosynthesis of ceramides. Allergic
Bing Han et al.
PloS one, 6(2), e17236-e17236 (2011-03-02)
The great advances of nanomaterials have brought out broad important applications, but their possible nanotoxicity and risks have not been fully understood. It is confirmed that exposure of environmental particulate matter (PM), especially ultrafine PM, are responsible for many lung
J G Martin et al.
Canadian journal of physiology and pharmacology, 70(4), 597-601 (1992-04-01)
Airway responsiveness to methacholine and other bronchoconstrictors is highly variable within and among species. The aim of the experiments in this report was to evaluate the importance of the quantity of airway smooth muscle as a determinant of intra- and
Sue R Downie et al.
Journal of applied physiology (Bethesda, Md. : 1985), 114(6), 770-777 (2013-02-02)
The forced oscillation technique (FOT) and multiple-breath nitrogen washout (MBNW) are noninvasive tests that are potentially sensitive to peripheral airways, with MBNW indexes being especially sensitive to heterogeneous changes in ventilation. The objective was to study methacholine-induced changes in the
Martijn C Nawijn et al.
PloS one, 8(2), e55307-e55307 (2013-02-09)
Asthma is a chronic inflammatory disease of the airways characterized by variable airway obstruction and airway hyperresponsiveness (AHR). The T regulatory (Treg) cell subset is critically important for the regulation of immune responses. Adoptive transfer of Treg cells has been
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