UNII:M73AI9718D

Names

[ CAS No. ]:
333-31-3

[ Name ]:
UNII:M73AI9718D

[Synonym ]:
2-Acetoxy-N,N,N-trimethyl-1-propanaminium bromide
METHYLCHOLINE BROMIDE
UNII:M73AI9718D
metacholine
ACETYL-B-METHYLCHOLINE BROMIDE
Acetyl-β-methylcholine bromide
Acetyl-beta-methylcholine bromide
O-Acetyl-β-methylcholine Bromide
MECHOLYL BROMIDE
ACETYL SS-METHYLCHOLINE BROMIDE
MFCD00011816
1-Propanaminium, 2-(acetyloxy)-N,N,N-trimethyl-, bromide (1:1)
Methacholine
2-acetoxy-n,n,n-trimethylpropan-1-aminium bromide
EINECS 206-372-2
1-Propanaminium, 2-(acetyloxy)-N,N,N-trimethyl-, bromide

Biological Activity

[Description]:

Methacholine (Acetyl-β-methylcholine) bromide is a potent muscarinic-3 (M3) agonist. Methacholine bromide acts directly on acetylcholine receptors on smooth muscle causing bronchoconstriction and airway narrowing. Methacholine bromide shows a high sensitivity to identify bronchial hyperresponsiveness (BHR). Methacholine bromide can be used to measure airway hyperresponsiveness (AHR) as a diagnostic aid in the assessment of individuals with asthma-like symptoms and normal resting expiratory flow rates[1][2][3][4].

[Related Catalog]:

Signaling Pathways >> Neuronal Signaling >> mAChR

Research Areas >> Cardiovascular Disease

Signaling Pathways >> GPCR/G Protein >> mAChR

[In Vivo]

Methacholine bromide (0.5 µg/kg plus 5 µg/kg/min for 30 min) induces bronchoconstriction in dogs[4]. Methacholine bromide (0.5 mg/kg; i.v.) induces bronchoconstriction was inhibited by bradykinin (4-40 µg/kg; i.v.) in a a dose-dependent manner in mouse[5]. Animal Model: 9-week female BALB/c mice[6] Dosage: 0.03, 0.1, 0.3, 1 mg/kg Administration: I.v Result: Induced severe bronchoconstriction.

[References]

[1]. Cohen J, et al. Relationship between airway responsiveness to neurokinin A and methacholine in asthma. Pulm Pharmacol Ther. 2005;18(3):171-176.

[2]. Anderson SD, et al. Comparison of mannitol and methacholine to predict exercise-induced bronchoconstriction and a clinical diagnosis of asthma. Respir Res. 2009;10(1):4. Published 2009 Jan 23.

[3]. Cockcroft DW. Methacholine challenge methods. Chest. 2008;134(4):678-680.

[4]. Kabara S, et al. Differential effects of thiopental on methacholine- and serotonin-induced bronchoconstriction in dogs. Br J Anaesth. 2003 Sep;91(3):379-84.

[5]. Folkerts G, et al. Bradykinin causes inhibition of methacholine-induced bronchoconstriction in vivo in mice. Naunyn Schmiedebergs Arch Pharmacol. 2001 Jul;364(1):53-8.

[6]. Vitorasso RL, et al. Methacholine dose response curve and acceptability criteria of respiratory mechanics modeling. Exp Lung Res. 2020 Feb-Mar;46(1-2):23-31.

Chemical & Physical Properties

[ Melting Point ]:
147-149ºC(lit.)

[ Molecular Formula ]:
C₈H₁₈BrNO₂

[ Molecular Weight ]:
240.138

[ Exact Mass ]:
239.052078

[ PSA ]:
26.30000

MSDS

Click to get detail MSDS

Safety Information

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
36/37/38

[ Safety Phrases ]:
26-36

[ HS Code ]:
2923900090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2923900090

[ Summary ]:
2923900090 other quaternary ammonium salts and hydroxides。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:6.5%。General tariff:30.0%