Acetylcholine

Base Information

• Chemical Name: Acetylcholine
• CAS No.: 51-84-3
• Molecular Formula: C7H16 N O2
• Molecular Weight: 146.21
• Hs Code.: 2923900090
• European Community (EC) Number: 200-128-9
• UNII: N9YNS0M02X
• DSSTox Substance ID: DTXSID8075334
• Nikkaji Number: J4.127K
• Wikipedia: Acetylcholine
• Wikidata: Q180623
• NCI Thesaurus Code: C77840
• RXCUI: 194
• Pharos Ligand ID: RN9JTC51H81M
• Metabolomics Workbench ID: 37488
• ChEMBL ID: CHEMBL667
• Mol file: 51-84-3.mol

Synonyms:2-(Acetyloxy)-N,N,N-trimethylethanaminium;Acetilcolina Cusi;Acetylcholine;Acetylcholine Bromide;Acetylcholine Chloride;Acetylcholine Fluoride;Acetylcholine Hydroxide;Acetylcholine Iodide;Acetylcholine L Tartrate;Acetylcholine L-Tartrate;Acetylcholine Perchlorate;Acetylcholine Picrate;Acetylcholine Picrate (1:1);Acetylcholine Sulfate (1:1);Bromide, Acetylcholine;Bromoacetylcholine;Chloroacetylcholine;Cusi, Acetilcolina;Fluoride, Acetylcholine;Hydroxide, Acetylcholine;Iodide, Acetylcholine;L-Tartrate, Acetylcholine;Miochol;Perchlorate, Acetylcholine

Chemical Property of Acetylcholine

Chemical Property:

• Refractive Index: 1.4500 (estimate)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 26.30000
• Density: g/cm³
• LogP: 0.25570
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 146.118103753
• Heavy Atom Count: 10
• Complexity: 115

Purity/Quality:

99% , ^*data from raw suppliers

Acetylcholine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)OCC[N+](C)(C)C
• Recent ClinicalTrials: Hot Flashes and Neurovascular Function in Women
• Recent NIPH Clinical Trials: The effect of the transdermal acetylcholine esterase inhibitors on frontal lobe function in Alzhemer's disease patients
• 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: neurotransmitter (ester of choline and acetic acid) 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).
• 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.
• 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.

Technology Process of Acetylcholine

There total 6 articles about Acetylcholine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

cholin hydroxide (123-41-1) + acetic acid (64-19-7,77671-22-8) → acetylcholine (51-84-3)

Guidance literature:

in Gegenwart eines Enzyms aus Schweineduenndarm-Presssaft;

Reference yield:

2-(dimethylamino)ethyl acetate (1421-89-2) + dimethyliodonium (24400-13-3) → acetylcholine (51-84-3) + methyl iodide (74-88-4)

Guidance literature:

at 25.85 ℃; Rate constant;

DOI:10.1021/ja982549s

Reference yield:

→ acetylcholine (51-84-3)

Guidance literature:

Acetylierung durch Cholin-Acetylase;

upstream raw materials:

cholin hydroxide

acetic acid

2-(dimethylamino)ethyl acetate

dimethyliodonium

Downstream raw materials:

betaine

dihydrogen peroxide

cholin hydroxide

acetic acid

Refernces

• 1、 Deakyne, Carol A.,Meot-Ner, Michael. "Ionic hydrogen bonds in bioenergetics. 4. Interaction energies of acetylcholine with aromatic and polar molecules". . p. 1546 - 1557. Retrieved 2007/10/03.