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Acetylcholine chloride

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Acetylcholine chloride Basic information

Product Name:
Acetylcholine chloride
Synonyms:
  • (2-Hydroxyethyl)trimethylammoniumchlorideacetate
  • 2-(acetyloxy)-n,n,n-trimethyl-ethanaminiuchloride
  • ACETYLCHOLINE CHLORIDE
  • ACETYLCHOLINI CHLORIDUM
  • ACH
  • ACECOLINE
  • acecholin
  • acetylcholinehydrochloride
CAS:
60-31-1
MF:
C7H16ClNO2
MW:
181.66
EINECS:
200-468-8
Product Categories:
  • Ammonium Chlorides (Quaternary)
  • Quaternary Ammonium Compounds
  • A-AM
  • Bioactive Small Molecules
  • Building Blocks
  • ACECOLINE
  • C6 to C7
  • Carbonyl Compounds
  • Cell Biology
  • Chemical Synthesis
  • Esters
  • Organic Building Blocks
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
Mol File:
60-31-1.mol
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Acetylcholine chloride Chemical Properties

Melting point:
146-150 °C (lit.)
Density 
1.1235 (rough estimate)
refractive index 
1.5560 (estimate)
storage temp. 
room temp
solubility 
H2O: 0.1 g/mL, clear, colorless
form 
Crystalline Powder
color 
White
Water Solubility 
Soluble IN COLD WATER
Sensitive 
Hygroscopic
Merck 
14,87
BRN 
3571875
Stability:
Stable. Substances to be avoided include strong oxidizing agents. Protect from moisture - very hygroscopic.
CAS DataBase Reference
60-31-1(CAS DataBase Reference)
EPA Substance Registry System
Ethanaminium, 2-(acetyloxy)-N,N,N-trimethyl-, chloride (60-31-1)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-37/39-36
WGK Germany 
2
RTECS 
FZ9800000
3-8-10-21
TSCA 
Yes
HazardClass 
IRRITANT
HS Code 
29379000
Toxicity
LD50 in mice, rats (mg/kg): 20, 22 i.v., 170, 250 s.c., 3000, 2500 i.p. (Molitor)

MSDS

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Acetylcholine chloride Usage And Synthesis

Description

Acetylcholine is a neurotransmitter that binds to nicotinic and muscarinic acetylcholine receptors (AChRs) in the central and peripheral nervous systems. It mediates motor function at the neuromuscular junction but also has functions in the parasympathetic and sympathetic nervous systems. It is involved in learning and memory through actions at nicotinic AChRs in the CNS. The actions of acetylcholine are terminated primarily via the action of acetylcholinesterase, which breaks it down into acetate and choline. Acetylcholine (chloride) mimics the effects of acetylcholine and has been used to determine the function of acetylcholine in various biological processes. Acetylcholine (chloride) inhibits peptide aggregation of p53 mutants in vitro at micromolar concentrations. It increases alveolar fluid clearance in a dose-dependent manner and enhances Na+/K+-ATPase activity, effects which are blocked by atropine , in a mouse model of pulmonary edema.

Chemical Properties

White or almost white crystalline powder or colourless crystals, very hygroscopic.

Uses

Acetylcholine Chloride is a cholinergic.

Uses

cholinergic, antiarrhythmic, miotic, vasodilator (peripheral)

Uses

endogenous neurotransmitter at cholinergic synapses; amplifies sarcolemma action potential inducing muscle contractions

Uses

A cholinergic neurotransmitter that can induce the opening of calcium channels

Definition

ChEBI: The chloride salt of acetylcholine, and a parasympatomimetic drug.

brand name

Miochol (Novartis).

General Description

ACh chloride exerts a powerfulstimulant effect on the parasympathetic nervous system.Attempts have been made to use it as a cholinergic agent,but its duration of action is too short for sustained effects,because of rapid hydrolysis by esterases and lack of specificitywhen administered for systemic effects. It is a cardiacdepressant and an effective vasodilator. Stimulation of thevagus and the parasympathetic nervous system produces atonic action on smooth muscle and induces a flow from thesalivary and lacrimal glands. Its cardiac-depressant effectresults from (a) a negative chronotropic effect that causes adecrease in heart rate and (b) a negative inotropic action onheart muscle that produces a decrease in the force of myocardialcontractions.

Biological Activity

Endogenous neurotransmitter. Acts at nicotinic and muscarinic acetylcholine receptors.

Biochem/physiol Actions

Acetylcholine chloride, injected at 20 mg/kg body weight, reduces mortality and plasma proinflammatory cytokines in mice with experimentally-induced sepsis . The cholinergic anti-inflammatory mechanism is probably mediated by interaction of acetylcholine with α7n cholinoreceptor on monocytes, macrophages, and neutrophils, which decreases the levels of proinflammatory cytokines such as TNF-α, IL-1β, and IL-6.

Clinical Use

Atropine blocks the depressant effect of ACh on cardiacmuscle and its production of peripheral vasodilation (i.e.,muscarinic effects) but does not affect the skeletal musclecontraction (i.e., nicotinic effect) produced.ACh chloride is a hygroscopic powder that is available inan admixture with mannitol to be dissolved in sterile waterfor injection shortly before use. It is a short-acting mioticwhen introduced into the anterior chamber of the eye and isespecially useful after cataract surgery during the placementof sutures. When applied topically to the eye, it has littletherapeutic value because of poor corneal penetration andrapid hydrolysis by AChE.

Safety Profile

Poison by subcutaneous, intravenous, and parenteral routes. Moderately toxic by ingestion. When heated to decomposition it emits very toxic fumes of NOx, and Cl-. A cholinergic agent. See also CHOLINE ACETATE (ESTER).

Purification Methods

It is very soluble in H2O (>10%), and is very hygroscopic. If pasty, dry it in a vacuum desiccator over H2SO4 until a solid residue is obtained. Dissolve this in absolute EtOH, filter it and add dry Et2O, when the hydrochloride separates. Collect by filtration and store it under very dry conditions. [Jones & Major J Am Chem Soc 52 307 1930.] The chloroplatinate crystallises from hot H2O in yellow needles and can be recrystallised from 50% EtOH, m 242-244o [Dudley Biochem J 23 1069 1929]; other m given is 256-257o. The perchlorate crystallises from EtOH as prisms m 116-117o. [J Am Pharm Assocn 36 272 1947, Beilstein 4 IV 1446.]

Acetylcholine chloride Preparation Products And Raw materials

Raw materials

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