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51-84-3

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51-84-3 Usage

Description

Acetylcholine is stored in vesicles in the presynaptic neuron. These fuse with presynaptic membrane upon stimulation by a nerve signal, thus, generating a pulse of neurotransmitter, which diffuses across the membrane. Acetylcholine may either bind reversibly to one of two different types of acetylcholine receptors on the postsynaptic membrane or be destroyed by the acetylcholine-hydrolyzing enzyme, acetylcholinesterase.

Uses

Different sources of media describe the Uses of 51-84-3 differently. You can refer to the following data:
1. neurotransmitter (ester of choline and acetic acid)
2. Acetylcholine is an endogenous neurotransmitter. It was the first neurotransmitter to be discovered. There are commercially available drugs that either block or mimic actions of acetylcholine. Commercial drugs used as cholinergic agonists mimic the action of acetylcholine (e.g. bethanechol, carbachol, and pilocarpine). Cholinesterase inhibitors cause accumulation of acetylcholine and stimulation of the central nervous system, glands, and muscles. Some nerve agents such as the gas Sarin and organophosphate pesticides are examples. Clinically, acetylcholinesterase inhibitors are employed to treat myasthenia gravis and Alzheimer’s disease. Acetylcholine receptor antagonists are antimuscarinic agents (atropine, scopolamine), ganglionic blockers (hexamethonium, mecamylamine), and neuromuscular blockers (tubocurarine, pancuronium, succinylcholine).

Brand name

Miochol (Novartis).

Biological Functions

The discovery that ACh was a transmitter in the peripheral nervous system formed the basis for the theory of neurotransmission. ACh is also a neurotransmitter in the mammalian brain; however, only a few cholinergic tracts have been clearly delineated.ACh is an excitatory neurotransmitter in the mammalian CNS.There is good evidence that ACh (among other neurotransmitters) is decreased in certain cognitive disorders, such as Alzheimer’s disease.

Biological Activity

Acetylcholine is a neurotransmitter found in the nervous systems of all animals. It is involved in the control of functions as diverse as locomotion, digestion, cardiac rate, “fight and flight” responses, secretion, learning and memory. Cholinergic dysfunction is associated with neuromuscular diseases such as myasthenia gravis and neurodegenerative disorders such as Alzheimer disease. Studies of acetylcholine and cholinergic neurotransmission have played a key role in the development of nearly all aspects of our current understanding of chemical synaptic transmission. In the early part of the twentieth century, pioneering physiological and neurochemical experiments resulted in establishing the principle that release of neuroactive compounds, such as acetylcholine, on to effector cells or other neurons forms the basis of most types of intercellular communication. In these early studies, application of acetylcholine could mimic the effects of nerve stimulation on muscle contraction, the rate of heart beating, etc., and the compound was thus identified as the first neurotransmitter substance. It was also noted that not all nerves released acetylcholine when stimulated, thus indicating specificity for the type of neurotransmitter substances present in particular neurons. Pharmacological work identified compounds, extracted primarily from plants, which differentially blocked the action of acetylcholine on particular types of effector cells, leading to the concept of receptor specificity. The quantal nature of neurotransmitter release was also first appreciated at cholinergic neuromuscular junctions. Finally, the nicotinic acetylcholine receptor was the first ligand-gated ion channel to have its amino acid sequence established. Acetylcholine is a simple ester of the quaternary amino alcohol choline and acetic acid. Acetylcholine is positively charged at physiological pH, is freely soluble in water (usually supplied as a bromide or chloride salt) and is subject to rapid hydrolysis in solution by heat or alkali. Nuclear magnetic resonance studies indicate considerable flexibility of the molecule in solution, and different conformations are thought to bind to different types of acetylcholine receptor.

Mechanism of action

Acetylcholine functions primarily as a chemical neurotransmitter in the nervous systems of all animals. When a cholinergic neuron is excited, it releases transmitter into the synaptic cleft where it can bind to a number of different receptor proteins. The receptors for acetylcholine can be classified into two general categories based primarily on the actions of different plant alkaloids that affect their function: nicotinic (nicotine binding) or muscarinic (muscarine binding). Several different subtypes for each of these general receptor classes have been characterized. The receptor binding event can be transduced into opening of cationic or anionic ion channels or coupled to some other metabolic signal such as phospholipid turnover rates or activation of second-messenger systems. Both inhibitory or, more commonly, excitatory responses are induced in the neurons or effector cells which receive the neurotransmitter signal, making acetylcholine-mediated neurotransmission particularly versatile. In addition to the ubiquitous presence of acetylcholine in the nervous systems of all animals, it is also found in a limited number of plants, bacteria, fungi and protozoa. This widespread distribution in a variety of species most likely indicates the appearance of acetylcholine-metabolizing proteins fairly early in evolutionary history. In vertebrates, acetylcholine is also found in non-neuronal tissues such as primate placenta and sperm where its functional role, if any, remains unknown.

Clinical Use

The cholinergic system was the first neurotransmitter system shown to have a role in wakefulness and initiation of REM sleep. Because of the poor penetration of the cholinergic drugs into the CNS, the role of this system in sleep has relied on animal studies using microinjection into the brain, primarily in the area of the dorsal pontine tegmentum. Acetylcholine, cholinergic agonists (e.g., arecoline or bethanechol), and cholinesterase inhibitors are effective in the initiation of REM sleep from NREM sleep after microinjection. Conversely, administration of anticholinergic drugs (e.g., atropine or scopolamine) hinders the transition to REM sleep. Increase in the rate of discharge of these cholinergic cells (that activate the thalamus, cerebral cortex, and hippocampus) during REM sleep parallel the same pattern seen with arousal and alertness.

Environmental Fate

Cholinergic agents can increase the acetylcholine level at the synaptic junction and cause rapid firing of the postsynaptic membrane. Antiacetylcholinesterase agents block the acetylcholinesterase enzyme and thus increase the acetylcholine level in the synapse causing rapid firing of the postsynaptic membrane.

Metabolism

Acetylcholine in the synapse can bind with cholinergic receptors on the postsynaptic or presynaptic membranes to produce a response. Free acetylcholine that is not bound to a receptor is hydrolyzed by AChE. This hydrolysis is the physiologic mechanism for terminating the action of acetylcholine. Enough AChE is present in the synapse to hydrolyze approximately 3 × 108 molecules of acetylcholine in 1 millisecond; thus, adequate enzyme activity exists to hydrolyze all the acetylcholine (~3 × 106 molecules) released by one action potential. A number of useful therapeutic cholinomimetic agents have been developed based on the ability of the compounds to inhibit AChE; these agents are addressed later in this chapter.

Check Digit Verification of cas no

The CAS Registry Mumber 51-84-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 1 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 51-84:
(4*5)+(3*1)+(2*8)+(1*4)=43
43 % 10 = 3
So 51-84-3 is a valid CAS Registry Number.
InChI:InChI=1/C7H16NO2/c1-7(9)10-6-5-8(2,3)4/h5-6H2,1-4H3/q+1

51-84-3Synthetic route

cholin hydroxide
123-41-1

cholin hydroxide

acetic acid
64-19-7

acetic acid

acetylcholine
51-84-3

acetylcholine

Conditions
ConditionsYield
in Gegenwart eines Enzyms aus Schweineduenndarm-Presssaft;
In water at 20℃; for 24h;
2-(dimethylamino)ethyl acetate
1421-89-2

2-(dimethylamino)ethyl acetate

dimethyliodonium
24400-13-3

dimethyliodonium

A

acetylcholine
51-84-3

acetylcholine

B

methyl iodide
74-88-4

methyl iodide

Conditions
ConditionsYield
at 25.85℃; Rate constant;
methyl iodide
74-88-4

methyl iodide

acetic acid-<2-dimethyl-amino-ethyl ester>

acetic acid-<2-dimethyl-amino-ethyl ester>

acetylcholine
51-84-3

acetylcholine

Conditions
ConditionsYield
With diethyl ether Salze des O-Acetyl-cholins;
choline acetate

choline acetate

acetylcholine
51-84-3

acetylcholine

Conditions
ConditionsYield
at 100℃;
2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

choline acetate

choline acetate

acetylcholine
51-84-3

acetylcholine

Conditions
ConditionsYield
With lead(IV) acetate; acetic acid at 20℃;
acetylcholine
51-84-3

acetylcholine

betaine
107-43-7

betaine

Conditions
ConditionsYield
With potassium permanganate; sulfuric acid
acetylcholine
51-84-3

acetylcholine

cholin hydroxide
123-41-1

cholin hydroxide

Conditions
ConditionsYield
bei der Spaltung durch ein im Presssaft aus Schweineduenndarm enthaltenes Enzym;
acetylcholine
51-84-3

acetylcholine

A

choline
62-49-7

choline

B

acetic acid
64-19-7

acetic acid

Conditions
ConditionsYield
Hydrolysis;
With water; acetylcholinesterase In acetonitrile Inert atmosphere; Enzymatic reaction;
acetylcholine
51-84-3

acetylcholine

dihydrogen peroxide
7722-84-1

dihydrogen peroxide

p,p'-diaminobiphenyl
92-87-5

p,p'-diaminobiphenyl

4-amino-4'-nitrobiphenyl
1211-40-1

4-amino-4'-nitrobiphenyl

Conditions
ConditionsYield
in alkal.Loesung;
acetylcholine
51-84-3

acetylcholine

choline
62-49-7

choline

Conditions
ConditionsYield
With acetylcholinesterase Enzyme kinetics;
With acetylcholinesterase In aq. buffer at 37℃; pH=9; Temperature; pH-value; Concentration; Enzymatic reaction;
With immobilized acetylcholinesterase Kinetics; Flow reactor; Enzymatic reaction;
With water In aq. phosphate buffer; dimethyl sulfoxide Kinetics; Catalytic behavior; Reagent/catalyst;
With acetylcholine esterase In aq. buffer at 37℃; Enzymatic reaction;
acetylcholine
51-84-3

acetylcholine

cucurbit[7]uril

cucurbit[7]uril

C7H16NO2(1+)*C42H42N28O14

C7H16NO2(1+)*C42H42N28O14

Conditions
ConditionsYield
In water
acetylcholine
51-84-3

acetylcholine

A

cholin hydroxide
123-41-1

cholin hydroxide

B

acetic acid
64-19-7

acetic acid

Conditions
ConditionsYield
With water at 80℃; pH=4.6; Kinetics; aq. acetate buffer;
acetylcholine
51-84-3

acetylcholine

A

betaine
107-43-7

betaine

B

dihydrogen peroxide
7722-84-1

dihydrogen peroxide

Conditions
ConditionsYield
Stage #1: acetylcholine With acetylcholinesterase In aq. buffer at 37℃; pH=9; Enzymatic reaction;
Stage #2: With choline oxidase In aq. buffer at 37℃; pH=9; Concentration; pH-value; Temperature; Enzymatic reaction;
acetylcholine
51-84-3

acetylcholine

C69H72N4O9
1419183-56-4

C69H72N4O9

C69H72N4O9*C7H16NO2(1+)

C69H72N4O9*C7H16NO2(1+)

Conditions
ConditionsYield
In methanol
acetylcholine
51-84-3

acetylcholine

C57H66N4O9
1217438-75-9

C57H66N4O9

C57H66N4O9*C7H16NO2(1+)

C57H66N4O9*C7H16NO2(1+)

Conditions
ConditionsYield
In methanol Activation energy;

51-84-3Relevant articles and documents

Solubility of acyclovir in nontoxic and biodegradable ionic liquids: COSMO-RS prediction and experimental verification

Lotfi, Meysam,Moniruzzaman, Muhammad,Sivapragasam, Magaret,Kandasamy, Shalini,Abdul Mutalib,Alitheen, Noorjahan Banu,Goto, Masahiro

, p. 124 - 131 (2017)

The pharmaceutical industry faces a challenge to find potential solvents for drug molecules that are sparingly soluble in water and conventional organic solvents. Recently, ionic liquids (ILs) have attracted great attention as pharmaceutical solvents owin

Enzymatic synthesis of a compound with acetylcholine-like biological

NACHMANSOHN,HESTRIN,VORIPAIEFF

, p. 875 - 877 (2007/12/05)

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