60-31-1 Usage
Description
Acetylcholine chloride, also known as ACh chloride, is a parasympathomimetic drug and the chloride salt of acetylcholine. It is a neurotransmitter that binds to nicotinic and muscarinic acetylcholine receptors (AChRs) in the central and peripheral nervous systems. ACh chloride exerts a powerful stimulant effect on the parasympathetic nervous system and is involved in motor function at the neuromuscular junction, as well as in the parasympathetic and sympathetic nervous systems. It also plays a role 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. It is a white or almost white crystalline powder or colorless crystals, very hygroscopic.
Uses
1. Used in Pharmaceutical Industry:
Acetylcholine chloride is used as a cholinergic agent for its ability to exert a powerful stimulant effect on the parasympathetic nervous system. It is also used as an antiarrhythmic, miotic, and vasodilator (peripheral) due to its various physiological effects.
2. Used in Neuromuscular Research:
Acetylcholine chloride is used as an endogenous neurotransmitter at cholinergic synapses for amplifying sarcolemma action potential, inducing muscle contractions, and studying the function of acetylcholine in various biological processes.
3. Used in Cardiology:
Acetylcholine chloride is used as a cardiac depressant for its negative chronotropic effect, which causes a decrease in heart rate, and its negative inotropic action on heart muscle, producing a decrease in the force of myocardial contractions.
4. Used in Pulmonary Research:
Acetylcholine chloride is used to increase alveolar fluid clearance in a dose-dependent manner and enhance Na+/K+-ATPase activity, effects which are blocked by atropine, in a mouse model of pulmonary edema.
5. Used in Protein Aggregation Research:
Acetylcholine chloride is used to inhibit peptide aggregation of p53 mutants in vitro at micromolar concentrations, providing insights into protein misfolding and aggregation-related diseases.
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 60-31-1 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 0 respectively; the second part has 2 digits, 3 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 60-31:
(4*6)+(3*0)+(2*3)+(1*1)=31
31 % 10 = 1
So 60-31-1 is a valid CAS Registry Number.
InChI:InChI=1/C7H16NO2.ClH/c1-7(9)10-6-5-8(2,3)4;/h5-6H2,1-4H3;1H/q+1;/p-1
60-31-1Relevant articles and documents
Inhibition of Choline Acetate Hydrolysis in the Presence of a Macrocyclic Polyphenolate
Schneider, Hans-Joerg,Schneider, Ulrich
, p. 1613 - 1615 (1987)
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Modular incorporation of 1-benzyltryptophan into dipeptide hosts that bind acetylcholine in pure water
Beshara, Cory S.,Hof, Fraser
experimental part, p. 1009 - 1016 (2011/02/16)
Proteins that recognize and bind quaternary ammonium ions depend on " aromatic-cage " structural motifs that use multiple aromatic residues to engage the side chain's ammonium cation. We introduce herein the use of 1-benzyltryp- tophan (Trp(Bn)) residues as synthetic, unnatural partial analogues of natural aromatic cages. We demonstrate the modular incorporation of these building blocks into simple dipeptide hosts and show that they are capable of binding quaternary ammonium ions in buffered water and in chloroform.
Binding of acetylcholine and tetramethylammonium to flexible cyclophane receptors: Improving on binding ability by optimizing host's geometry
Sarri, Paolo,Venturi, Francesca,Cuda, Francesco,Roelens, Stefano
, p. 3654 - 3661 (2007/10/03)
The structure of a cyclophanic tetraester (1), previously employed for investigations on the cation-π interaction, has been optimized to better accommodate acetylcholine (ACh) and tetramethylammonium (TMA) guests. Following indications from molecular modeling calculations, a flexible cyclophane receptor of significantly improved binding properties has been obtained by removing the four carbonyl groups of the parent host. 2,11,20,29-Tetraoxa[3.3.3.3]paracyclophane (2) was prepared by an improved procedure, which was conveniently devised to avoid the formation of contiguous cyclooligomers that caused serious separation issues. Association of 2 with TMA picrate was measured in CDCl3 at T = 296 K by 1H NMR titrations and compared to binding data obtained for a set of reference hosts, including the parent tetraester 1, the corresponding cyclophanic tetraamine, the open-chain counterpart of 2, and its cyclooligomers from pentamer to octamer. Binding enhancements ranging from 15-fold (with respect to the tetraester and the tetraamine) to over 80-fold (with respect to the open-chain tetraether) were achieved by geometry optimization of the host. Binding of 2 to ACh and TMA was investigated for a variety of counterions. A constant binding free energy increment of nearly 8 kJ mol-1 with respect to 1 was observed, independent from the anion and irrespective of the different structure of the cationic guests. Results showed that the electrostatic inhibiting contribution of the counterion to the cation's binding is a characteristic constant of each anion. The value of -ΔG° = 44.9 kJ mol-1 extrapolated for TMA in the absence of a counterion indicates that 28-34 kJ mol-1 of binding free energy are lost in ion pairing.