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acetylcholine

File:Acetylcholine-skeletal-formula.svg · Wikimedia Commons · See Wikimedia Commons

EntityQ180623· pop 64· linked from 2,072 articles

acetylcholine

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Also known as ACh, E1001, O-acetylcholine, choline acetate, 2-acetoxyethyl(trimethyl)ammonium, 2-acetyloxyethyl(trimethyl)ammonium, 2-acetyloxyethyl(trimethyl)azanium, [2-(acetyloxy)ethyl]trimethylazanium

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.

OverviewAI-generated

Acetylcholine is a chemical compound with the formula C₇NH₁₆O₂⁺. Its IUPAC name is 2-acetyloxyethyl(trimethyl)azanium. The substance has a mass of 146.118 and a weight of 146.21. It carries a charge of 1.

Chemical properties include an xlogp of 0.2 and a tpsa of 26.3. The molecule contains 0 hydrogen bond donors and 2 hydrogen bond acceptors. Its canonical SMILES notation is CC(=O)OCC[N+](C)(C)C.

Acetylcholine is referenced by 2,072 other encyclopedia articles. A search for the term yields 106,770 results in the PubMed database.

Synthesized by Vinony from 18 facts across 4 sources: Wikidata, PubChem, PubMed, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

Key facts

Drug.image
Acetylcholine-skeletal-formula.svg
Drug.image_class
skin-invert-image
Drug.source_tissues
motor neurons, parasympathetic nervous system, brain
Drug.target_tissues
smooth muscles, brain, many other organs
Drug.receptors
nicotinic, muscarinic
Drug.agonists
nicotine, muscarine, cholinesterase inhibitors
Drug.antagonists
tubocurarine, atropine
Drug.precursor
choline, acetyl-CoA
Drug.biosynthesis
choline acetyltransferase
Drug.metabolism
acetylcholinesterase
Drug.DailyMedID
Acetylcholine
Drug.ATC_prefix
S01
Drug.ATC_suffix
EB09
Drug.CAS_number
51-84-3
Drug.PubChem
187
Drug.IUPHAR_ligand
294
Drug.DrugBank
EXPT00412
Drug.ChemSpiderID
182

via Wikipedia infobox

Chemical data

Formula
C7H16NO2+
Molecular weight
146.21 g/mol
IUPAC name
2-acetyloxyethyl(trimethyl)azanium
SMILES
CC(=O)OCC[N+](C)(C)C
InChIKey
OIPILFWXSMYKGL-UHFFFAOYSA-N
XLogP
0.2
Polar surface area
26.3 Ų
H-bond donors
0
H-bond acceptors
2
Formal charge
1

via PubChem

Research

106,770 papers

via PubMed

Wikidata facts

Has part
carbon
Mass
146.118
Has use
medication
Show 7 more facts
Commons category
Acetylcholine
topic's main category
Category:Acetylcholine
chemical formula
C₇NH₁₆O₂⁺
canonical SMILES
CC(=O)OCC[N+](C)(C)C
found in taxon
Vigna unguiculata
subject has role
primary metabolite
different from
acetyl chloride
Sources (7)

via Wikidata · CC0

~23 min read

Encyclopedic overview

23 sections
Contents
  • Chemistry
  • Biochemistry
  • Functions
  • Cellular effects
  • Neuromuscular junction
  • Autonomic nervous system
  • Direct vascular effects
  • Central nervous system
  • Memory
  • Diseases and disorders
  • Myasthenia gravis
  • Pharmacology
  • Nicotinic receptors
  • Muscarinic receptors
  • Cholinesterase inhibitors
  • Synthesis inhibitors
  • Release inhibitors
  • Photopharmacological agents
  • Comparative biology and evolution
  • History
  • References
  • Further reading
  • External links

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.

Excerpted from Wikipedia’s “acetylcholine” article, available under the CC BY-SA 4.0 licence.

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