(2-Acetoxyethyl)trimethylammonium
ACETYLECHOLINE · O-Acetylcholine · (2-acetoxyethyl)trimethylammonium · Acetylcholine · Acetylcholine Monomer · 2-acetyloxyethyl-trimethyl-ammonium · 2-Acetoxy-N,N,N-trimethylethan-1-aminium · (2-acetoxyethyl)trimethylammonium USP/EP/BP
Identifikatoren & physikalische Daten
| CAS No. | 14047-05-3 |
|---|---|
| Summenformel | C7H16NO2+ |
| Durchschnittliche Molmasse | 146,21 g/mol |
| Monoisotopische Masse | 146,11755517 g/mol |
| SMILES | CC(=O)OCC[N+](C)(C)C |
| InChIKey | OIPILFWXSMYKGL-UHFFFAOYSA-N |
| PubChem CID | 187 |
| ChEMBL | CHEMBL667 |
| ChEBI | CHEBI:15355 |
| EC No. | 200-128-9 |
| DTXSID | DTXSID8075334 |
| Lokaler Name | (2-Acetoxyethyl)trimethylammonium |
Chemische & physikalische Eigenschaften
| XLogP | 0,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 26,3 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 10 |
| Formalladung | 1 |
| Komplexität | 115 |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| Human Drugs | Breast FeedingLactationMioticsMuscarinic AgonistsParasympathomimetics |
| Schmelzpunkt | 148 °C |
| Physical Description | Solid |
| Ionization Efficiency | Positive3.382.7Agilent XCTElectrospray ionizationformic acid (5.3nM) |
| Collision Cross Section | 129.5 Ų [M]+ [CCS Type: DTMethod: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]129.7 Ų [M+H]+ [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)]130.1 Ų [M]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]129.2 Ų [M*]+ |
| Siedepunkt | 265.84°C (rough estimate) |
| Dichte | 1.0528 (rough estimate) |
| Brechungsindex | 1.4500 (estimate) |
| Löslichkeit | Water (easy), ethanol (easy), ether (not easy) |
| CAS Datenbank | 51-84-3 |
| EPA chemische Informationen | Acetylcholine (51-84-3) |
Sicherheit & Vorschriften
| GHS-Einstufung | Not Classified |
|---|---|
| Hazard Classes and Categories | Not Classified |
| Effects During Pregnancy and Lactation | ◉ Summary of Use during Lactation |
| UN-Transportnummer | 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 systemparasympathetic postganglionic neuronsand 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. |
| Gefahrenklasse | 8 |
| Verpackungsgruppe | II |
Anwendungen & Verwendung
Beschreibung
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.
Beschreibung
Acetylcholine 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.
Verwenden
Acetylcholine 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.
Verwenden
neurotransmitter (ester of choline and acetic acid)