Acetylcholine chloride

Acetylcholine chloride Basic information
Product Name:Acetylcholine chloride
Synonyms:(2-Hydroxyethyl)trimethylammoniumchlorideacetate;2-(acetyloxy)-n,n,n-trimethyl-ethanaminiuchloride;ACETYLCHOLINE CHLORIDE;ACETYLCHOLINI CHLORIDUM;ACECOLINE;acecholin;acetylcholinehydrochloride;acetylcholiniumchloride
CAS:60-31-1
MF:C7H16ClNO2
MW:181.66
EINECS:200-468-8
Product Categories:Ammonium Chlorides (Quaternary);Quaternary Ammonium Compounds;ACECOLINE;A-AM;Bioactive Small Molecules;Building Blocks;C6 to C7;Carbonyl Compounds;Cell Biology;Chemical Synthesis;Esters;Organic Building Blocks;Intermediates & Fine Chemicals;Pharmaceuticals
Mol File:60-31-1.mol
Acetylcholine chloride Structure
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.
LogP-3.904 (est)
CAS DataBase Reference60-31-1(CAS DataBase Reference)
EPA Substance Registry SystemEthanaminium, 2-(acetyloxy)-N,N,N-trimethyl-, chloride (60-31-1)
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
ToxicityLD50 in mice, rats (mg/kg): 20, 22 i.v., 170, 250 s.c., 3000, 2500 i.p. (Molitor)
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
Acetylcholine chloride Usage And Synthesis
DescriptionAcetylcholine 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 PropertiesWhite or almost white crystalline powder or colourless crystals, very hygroscopic.
UsesAcetylcholine Chloride is a cholinergic.
UsesA cholinergic neurotransmitter that can induce the opening of calcium channels
Usesendogenous neurotransmitter at cholinergic synapses; amplifies sarcolemma action potential inducing muscle contractions
Usescholinergic, antiarrhythmic, miotic, vasodilator (peripheral)
DefinitionChEBI: The chloride salt of acetylcholine, and a parasympatomimetic drug.
Brand nameMiochol (Novartis).
General DescriptionACh 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 ActivityEndogenous neurotransmitter. Acts at nicotinic and muscarinic acetylcholine receptors.
Biochem/physiol ActionsAcetylcholine 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 UseAtropine 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 ProfilePoison 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).
storageDesiccate at RT
Purification MethodsIt 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.]
INDIUM(III) CHLORIDE TETRAHYDRATE Thulium chloride POLYETHYLENE, CHLORINATED LAUROYLCHOLINE CHLORIDE SUCCINYLCHOLINE CHLORIDE DIHYDRATE {ACETYLCHOLINE CHLORIDE--N/ ACETYLCHOLINE CHLORIDE, [ACETYL-1-14C] CHOLINE ACETYLCHOLINE BROMIDE MYRISTOYL CHOLINE CHLORIDE Acetoxyacetic acid SILICON TETRAACETATE BENZOYLCHOLINE CHLORIDE SUBERYLDICHOLINE DICHLORIDE DIMETHYLPHOSPHINOTHIOIC CHLORIDE Ferric chloride PALMITOYL-CHOLINE CHLORIDE 2-​[[(2-​ethylphenyl)​(2-​hydroxyethyl)​amino]​methyl]​-​3,​3-​difluoro-Propanenitrile

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