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Methacholine chloride

Methacholine chloride structure

CAS No:
62-51-1
Formula:
C8H18NO2.Cl
Chemical Name:
Methacholine chloride
Synonyms:
1-Propanaminium,2-(acetyloxy)-N,N,N-trimethyl-,chloride (1:1);(2-Hydroxypropyl)trimethylammonium chloride acetate;Ammonium,(2-hydroxypropyl)trimethyl-,chloride,acetate;1-Propanaminium,2-(acetyloxy)-N,N,N-trimethyl-,chloride;(2-Acetoxypropyl)trimethylammonium chloride;Acetyl-β-methylcholine chloride;O-Acetyl-β-methylcholine chloride;Amechol;Methacholine chloride;Trimethyl-β-acetoxypropylammonium chloride;Mecholyl;β-Methylacetylcholine chloride;Mecholine chloride;(±)-Acetyl-β-methylcholine chloride;DL-Acetyl-β-methylcholine chloride;Provocholine;Arkofix NDC;2410-07-3
Categories:
Organic Chemistry > Amides

Description

Methacholine chloride is a synthetic choline ester that acts as a non-selective muscarinic receptor agonist in the parasympathetic nervous system.

Methacholine chloride is a quaternary ammonium salt. It contains a methacholine.|Methacholine Chloride is the chloride salt form of methacholine, a direct-acting cholinergic muscarinic agonist with bronchoconstrictive, miotic, vasodilator, and cardiac vagomimetic activity. Methacholine chloride acts directly on the muscarinic receptors in the heart, eye, and lung, thereby producing parasympathomimetic effects.|A quaternary ammonium parasympathomimetic agent with the muscarinic actions of ACETYLCHOLINE. It is hydrolyzed by ACETYLCHOLINESTERASE at a considerably slower rate than ACETYLCHOLINE and is more resistant to hydrolysis by nonspecific CHOLINESTERASES so that its actions are more prolonged. It is used as a parasympathomimetic bronchoconstrictor agent and as a diagnostic aid for bronchial asthma. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1116)

Methacholine chloride Basic Attributes

Molecular Weight：

195.69

Exact Mass：

195.102600

EC Number：

200-537-2

NSC Number：

757090

DSSTox ID：

DTXSID7023271

NCI Thesaurus Code：

C47607

HScode：

29239000

Characteristics

PSA：

26.3

Appearance：

powder

Density：

1.1028 (rough estimate)

Melting Point：

172 °C

Refractive Index：

1.5790 (estimate)

Water Solubility：

H2O: almost transparency;H2O: 50 mg/mL, clear, colorless

Storage Conditions：

2-8°C

Toxicity：

Oral-rat LD50: 750 mg/kg; Oral-Mouse LD50: 740 mg/kg

Flammability characteristics：

Flammable; decomposes by heating to release toxic chloride and nitrogen oxide fumes

Collision Cross Section：

134.8 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

22-36/37/38

safety instructions：

26-36

RTECS Number：

BR5250000

Marks：

Storage features：

Warehouse ventilated, low temperature and dry

Stability/Shelf Life：

Unstable - moisture sensitive. Incompatible with oxidizing agents.

Precautionary statement(s)：

P301 + P312 + P330-P305 + P351 + P338

Hazard Statements：

H302-H315-H319-H335

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 42 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Toxicity class：

moderately toxic

Drug Information

Drug Indication：

Diagnosis of asthma

MeSH：

Agents causing the narrowing of the lumen of a bronchus or bronchiole. (See all compounds classified as Bronchoconstrictor Agents.)|Drugs that mimic the effects of parasympathetic nervous system activity. Included here are drugs that directly stimulate muscarinic receptors and drugs that potentiate cholinergic activity, usually by slowing the breakdown of acetylcholine (CHOLINESTERASE INHIBITORS). Drugs that stimulate both sympathetic and parasympathetic postganglionic neurons (GANGLIONIC STIMULANTS) are not included here. (See all compounds classified as Parasympathomimetics.)|Agents causing contraction of the pupil of the eye. Some sources use the term miotics only for the parasympathomimetics but any drug used to induce miosis is included here. (See all compounds classified as Miotics.)|Drugs that bind to and activate muscarinic cholinergic receptors (RECEPTORS, MUSCARINIC). Muscarinic agonists are most commonly used when it is desirable to increase smooth muscle tone, especially in the GI tract, urinary bladder and the eye. They may also be used to reduce heart rate. (See all compounds classified as Muscarinic Agonists.)

MeSH Entry Terms：

2-(Acetyloxy)-N,N,N-trimethyl-1-propanaminium Chloride

Methacholine chloride Use and Manufacturing

Uses

antihypertensive, antianginal

Manufacturing Info：

1-Propanaminium, 2-(acetyloxy)-N,N,N-trimethyl-, chloride (1:1): ACTIVE

Use Classification：

Human Drugs -> EU pediatric investigation plans|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:195.69
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:195.1026065
Monoisotopic Mass:195.1026065
Topological Polar Surface Area:26.3
Heavy Atom Count:12
Complexity:138
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes