Acetylcholine (HCID 187)

Überblick

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.

Namen und Bezeichner

Bevorzugter Name: Acetylcholine
IUPAC: 2-acetyloxyethyl(trimethyl)azanium
Lokaler Name: (2-Acetoxyethyl)trimethylammonium
Englischer Name: Acetylcholine
Summenformel: C7H16NO2+
Molmasse: 146.21

Namen und Synonyme

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

Weitere Namen anzeigen

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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 0,2
Polarare Oberfläche (TPSA): 26,3 Å²
H-Brücken-Donoren: 0
H-Brücken-Akzeptoren: 2
Frei drehbare Bindungen: 4
Schwere Atome: 10
Formalladung: 1
Komplexität: 115

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15

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

Melting Point148 °C

Physical DescriptionSolid

Ionization Efficiency · 6 Einträge

Positive

3.38

2.7

Agilent XCT

Electrospray ionization

formic acid (5.3nM)

Collision Cross Section · 4 Einträge

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*]+

Physikochemische Eigenschaften

Siedepunkt: 265.84 °C · 265.84°C (rough estimate)
Dichte: 1.0528 · 1.0528 (rough estimate)
Brechungsindex: 1.45 · 1.4500 (estimate)
Löslichkeit: Water (easy), ethanol (easy), ether (not easy)
CAS Datenbank: 51 · 51-84-3
EPA chemische Informationen: Acetylcholine (51-84-3)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS ClassificationNot Classified

Gefahrenhinweise

Hazard Classes and CategoriesNot Classified

Toxikologische Informationen

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Sicherheitsdaten

ridadr: 1760
Toxizität: 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

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 3 Einträge

S01EB09

S - Sensory organs

QS - Sensory organs

FDA Pharmacological Classification · 5 Einträge

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 Einträge

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

Anwendungen · 4 Einträge

BeschreibungAcetylcholine 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.

BeschreibungAcetylcholine 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.

VerwendenAcetylcholine 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.

Verwendenneurotransmitter (ester of choline and acetic acid)