Acetylcholine (HCID 187)

Overview

Acetylcholine is actylcholine is an ester of acetic acid and choline, which acts as a neurotransmitter. It has a role as a hormone, a neurotransmitter, a vasodilator agent, a muscarinic agonist, a mouse metabolite and a human metabolite. It is an acylcholine and an acetate ester.

Names & identifiers

Preferred name: Acetylcholine
IUPAC: 2-acetyloxyethyl(trimethyl)azanium
English name: Acetylcholine
Molecular formula: C7H16NO2+
Molecular weight: 146.21

Names & synonyms

acetylcholine51-84-3O-AcetylcholineCholine acetate (ester)2-acetyloxyethyl(trimethyl)azanium2-(Acetyloxy)-N,N,N-trimethylethanaminiumethanaminium, 2-(acetyloxy)-N,N,N-trimethyl-N9YNS0M02XCHEBI:15355[2-(acetyloxy)ethyl]trimethylazanium2-acetyloxyethyl-trimethylazaniumDTXSID8075334

Show more names

ACETYLECHOLINE(2-acetoxyethyl)trimethylammoniumAcetylcholine Monomer2-acetyloxyethyl-trimethyl-ammonium2-Acetoxy-N,N,N-trimethylethan-1-aminium(2-acetoxyethyl)trimethylammonium USP/EP/BPEthanaminium,2-(acetyloxy)-N,N,N-trimethyl-AcetylcholineQ: What is Acetylcholine Q: What is the CAS Number of Acetylcholine

(2-(acetyloxy)ethyl)trimethylazaniumCusi, AcetilcolinaFluoride, AcetylcholineRefChem:5512Hydroxide, AcetylcholineAcetylcholine L TartrateL-Tartrate, AcetylcholineDTXCID6040951

Database identifiers

CAS: 14047-05-3、51-84-3
PubChem CID: 187
DTXSID: DTXSID8075334
ChEMBL: CHEMBL667
ChEBI: CHEBI:15355
UNII: N9YNS0M02X
EC Number: 200-128-9
Nikkaji: J4.127K

Properties

Computed structural properties

XLogP: 0.2
Topological polar surface area: 26.3 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 2
Rotatable bonds: 4
Heavy atoms: 10
Formal charge: 1
Complexity: 115

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15

Human DrugsBreast Feeding; Lactation; Miotics; Muscarinic Agonists; Parasympathomimetics

Melting Point148 °C

Physical DescriptionSolid

Ionization Efficiency · 6 items

Positive

3.38

2.7

Agilent XCT

Electrospray ionization

formic acid (5.3nM)

Collision Cross Section · 4 items

129.5 Å² [M]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

129.7 Å² [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

130.1 Å² [M]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

129.2 Å² [M*]+

Physicochemical properties

Boiling point: 265.84 °C · 265.84°C (rough estimate)
Density: 1.0528 · 1.0528 (rough estimate)
refractive index: 1.45 · 1.4500 (estimate)
solubility: Water (easy), ethanol (easy), ether (not easy)
CAS DataBase Reference: 51 · 51-84-3
NCI Dictionary of Cancer Terms: acetylcholine
FDA UNII: 9 YNS0M02X · N9YNS0M02X
ATC code: 1 EB09 · S01EB09
EPA Substance Registry System: Acetylcholine (51-84-3)
RIDADR: 1760 · 1760
HazardClass: 8 · 8
PackingGroup: II
Toxicity: The choline ester of acetic acid. ACh is released in vertebrates as the neurotransmitter for cholinergic neurons in the CNS, as well as at several peripheral locations: somatic neurons innervating skeletal muscle (neuromuscular junctions); preganglionic neurons in both divisions of the autonomic nervous system; parasympathetic postganglionic neurons; and a few sympathetic postganglionic neurons. ACh is synthesized from choline and acetyl CoA by the mitochondrial enzyme choline acetyltransferase. Cholinergic receptors (cholinoceptors), that mediate the effects of ACh, are generally classified as nicotinic or muscarinic, based on their binding preferences for nicotine and muscarine, respectively. ACh is hydrolyzed to choline and acetate by acetylcholinesterase, that is an important target for a variety of toxic and therapeutic anticholinesterases, such as the nerve agents, carbamate, and organophosphorus insecticides.

Safety & regulation

GHS classification

GHS ClassificationNot Classified

Hazard information

Hazard Classes and CategoriesNot Classified

Toxicology

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Safety data

ridadr: 1760
Toxicity: The choline ester of acetic acid. ACh is released in vertebrates as the neurotransmitter for cholinergic neurons in the CNS, as well as at several peripheral locations: somatic neurons innervating skeletal muscle (neuromuscular junctions); preganglionic neurons in both divisions of the autonomic nervous system; parasympathetic postganglionic neurons; and a few sympathetic postganglionic neurons. ACh is synthesized from choline and acetyl CoA by the mitochondrial enzyme choline acetyltransferase. Cholinergic receptors (cholinoceptors), that mediate the effects of ACh, are generally classified as nicotinic or muscarinic, based on their binding preferences for nicotine and muscarine, respectively. ACh is hydrolyzed to choline and acetate by acetylcholinesterase, that is an important target for a variety of toxic and therapeutic anticholinesterases, such as the nerve agents, carbamate, and organophosphorus insecticides.
hazard_class: 8
packing_group: II

Chemistry & industry

Pharmacology

ATC Code · 3 items

S01EB09

S - Sensory organs

QS - Sensory organs

FDA Pharmacological Classification · 5 items

N9YNS0M02X

ACETYLCHOLINE

Mechanisms of Action [MoA] - Cholinergic Agonists

Established Pharmacologic Class [EPC] - Cholinergic Receptor Agonist

Acetylcholine is a Cholinergic Receptor Agonist. The mechanism of action of acetylcholine is as a Cholinergic Agonist.

MeSH Pharmacological Classification · 2 items

Drugs used to cause dilation of the blood vessels.

Drugs that bind to and activate cholinergic receptors.

Tissue LocationsAdipose Tissue

Cellular LocationsCytoplasm

Metabolite PathwaysBetazole Action Pathway

Applications · 5 items

DescriptionAcetylcholine 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.

DescriptionAcetylcholine is a choline molecule that has been acetylated at the oxygen atom. Because of the presence of a highly polar, charged ammonium group, acetylcholine does not penetrate lipid membranes. Because of this, when the drug is introduced externally, it remains in the extracellular space and does not pass through the blood–brain barrier.

UsesAcetylcholine does not have therapeutic value as a drug for intravenous administration because of its multi-faceted action and rapid inactivation by cholinesterase. Likewise, it is possible for a collaptoid state to develop, and arterial pressure can rapidly fall and the heart can stop. However, it is used in the form of eye drops to cause miosis during cataract surgery, which makes it advantageous because it facilitates quick post-operational recovery.

UsesAcetylcholine 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).

Usesneurotransmitter (ester of choline and acetic acid)

Suppliers34 total

上海金试生化科技有限公司18601717983 18601717983 · [email protected]

武汉众志诚生物技术有限公司13628624121 13628604890 · [email protected]

广东元丰化学试剂有限公司0751-2829979 13318593351 · [email protected]

广东云星生物技术有限公司0751-18902340975/189023400307 18902340307 · [email protected]

江苏艾康生物医药研发有限公司025-5885952 15955137747 · [email protected]

Additional notes · 1 item

DefinitionChEBI: Acetylcholine is actylcholine is an ester of acetic acid and choline, which acts as a neurotransmitter. It has a role as a vasodilator agent, a muscarinic agonist, a hormone, a human metabolite, a mouse metabolite and a neurotransmitter. It is an acetate ester and an acylcholine.