CHEBI:15355 - acetylcholine

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name acetylcholine
ChEBI ID CHEBI:15355
Definition Actylcholine is an ester of acetic acid and choline, which acts as a neurotransmitter.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:40559, CHEBI:2416, CHEBI:12686, CHEBI:13715, CHEBI:22197
Supplier Information ChemicalBook:CB0895802, eMolecules:1985299, ZINC000003079336
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Acetylcholine (ACh) is an organic compound that functions in the brain and body of many types of animals (including humans) as a neurotransmitter. Its name is derived from its chemical structure: it is an ester of acetic acid and choline. Parts in the body that use or are affected by acetylcholine are referred to as cholinergic. Acetylcholine is the neurotransmitter used at the neuromuscular junction—in other words, it is the chemical that motor neurons of the nervous system release in order to activate muscles. This property means that drugs that affect cholinergic systems can have very dangerous effects ranging from paralysis to convulsions. Acetylcholine is also a neurotransmitter in the autonomic nervous system, both as an internal transmitter for both the sympathetic and the parasympathetic nervous system, and as the final product released by the parasympathetic nervous system. Acetylcholine is the primary neurotransmitter of the parasympathetic nervous system. In the brain, acetylcholine functions as a neurotransmitter and as a neuromodulator. The brain contains a number of cholinergic areas, each with distinct functions; such as playing an important role in arousal, attention, memory and motivation. Acetylcholine has also been found in cells of non-neural origins as well as microbes. Recently, enzymes related to its synthesis, degradation and cellular uptake have been traced back to early origins of unicellular eukaryotes. The protist pathogens Acanthamoeba spp. have shown evidence of the presence of ACh, which provides growth and proliferative signals via a membrane-located M1-muscarinic receptor homolog. Partly because of acetylcholine's muscle-activating function, but also because of its functions in the autonomic nervous system and brain, many important drugs exert their effects by altering cholinergic transmission. Numerous venoms and toxins produced by plants, animals, and bacteria, as well as chemical nerve agents such as sarin, cause harm by inactivating or hyperactivating muscles through their influences on the neuromuscular junction. Drugs that act on muscarinic acetylcholine receptors, such as atropine, can be poisonous in large quantities, but in smaller doses they are commonly used to treat certain heart conditions and eye problems. Scopolamine, or diphenhydramine, which also act mainly on muscarinic receptors in an inhibitory fashion in the brain (especially the M1 receptor) can cause delirium, hallucinations, and amnesia through receptor antagonism at these sites. So far as of 2016, only the M1 receptor subtype has been implicated in anticholinergic delirium. The addictive qualities of nicotine are derived from its effects on nicotinic acetylcholine receptors in the brain.
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Formula C7H16NO2
Net Charge +1
Average Mass 146.20748
Monoisotopic Mass 146.11756
InChI InChI=1S/C7H16NO2/c1-7(9)10-6-5-8(2,3)4/h5-6H2,1-4H3/q+1
InChIKey OIPILFWXSMYKGL-UHFFFAOYSA-N
SMILES CC(=O)OCC[N+](C)(C)C
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Homo sapiens (NCBI:txid9606) See: DOI
Roles Classification
Biological Role(s): human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
muscarinic agonist
Any drug that binds to and activates a muscarinic cholinergic receptor.
hormone
Originally referring to an endogenous compound that is formed in specialized organ or group of cells and carried to another organ or group of cells, in the same organism, upon which it has a specific regulatory function, the term is now commonly used to include non-endogenous, semi-synthetic and fully synthetic analogues of such compounds.
neurotransmitter
An endogenous compound that is used to transmit information across the synapse between a neuron and another cell.
Application(s): vasodilator agent
A drug used to cause dilation of the blood vessels.
muscarinic agonist
Any drug that binds to and activates a muscarinic cholinergic receptor.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing acetylcholine (CHEBI:15355) has role hormone (CHEBI:24621)
acetylcholine (CHEBI:15355) has role human metabolite (CHEBI:77746)
acetylcholine (CHEBI:15355) has role mouse metabolite (CHEBI:75771)
acetylcholine (CHEBI:15355) has role muscarinic agonist (CHEBI:38325)
acetylcholine (CHEBI:15355) has role neurotransmitter (CHEBI:25512)
acetylcholine (CHEBI:15355) has role vasodilator agent (CHEBI:35620)
acetylcholine (CHEBI:15355) is a acetate ester (CHEBI:47622)
acetylcholine (CHEBI:15355) is a acylcholine (CHEBI:35287)
Incoming acetylcholine bromide (CHEBI:55316) has part acetylcholine (CHEBI:15355)
acetylcholine chloride (CHEBI:2417) has part acetylcholine (CHEBI:15355)
IUPAC Name
2-acetyloxy-N,N,N-trimethylethanaminium
Synonyms Sources
Acetylcholine KEGG COMPOUND
ACETYLCHOLINE PDBeChem
acetylcholine UniProt
ACh ChemIDplus
Azetylcholin ChEBI
choline acetate ChemIDplus
O-Acetylcholine KEGG COMPOUND
Manual Xrefs Databases
65 DrugCentral
Acetylcholine Wikipedia
ACH PDBeChem
C01996 KEGG COMPOUND
DB03128 DrugBank
LSM-5888 LINCS
View more database links
Registry Numbers Types Sources
1764436 Beilstein Registry Number ChemIDplus
326108 Gmelin Registry Number Gmelin
51-84-3 CAS Registry Number ChemIDplus
Citations Waiting for Citations
Last Modified
22 February 2017