Acetylcholine (HCID 187)

概要

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.

名称と識別子

優先名称: Acetylcholine
IUPAC: 2-acetyloxyethyl(trimethyl)azanium
現地名: アセチルコリン
英語名: Acetylcholine
分子式: C7H16NO2+
分子量: 146.21

名称と別名

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

名称をさらに表示

(2-アセトキシエチル)トリメチルアンモニウムアセチルコリン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

データベース識別子

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

物性

構造計算による物性

XLogP: 0.2
極性表面積: 26.3 Å²
水素結合供与体数: 0
水素結合受容体数: 2
回転可能結合数: 4
重原子数: 10
形式電荷: 1
複雑度: 115

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15

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

Melting Point148 °C

Physical DescriptionSolid

Ionization Efficiency · 6 件

Positive

3.38

2.7

Agilent XCT

Electrospray ionization

formic acid (5.3nM)

Collision Cross Section · 4 件

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*]+

物理化学的性質

沸点: 265.84 °C · 265.84°C (rough estimate)
比重(密度): 1.0528 · 1.0528 (rough estimate)
屈折率: 1.45 · 1.4500 (estimate)
溶解性: 水(易),エタノール(易),エーテル(不)
CAS データベース: 51 · 51-84-3
EPAの化学物質情報: Acetylcholine (51-84-3)

安全と法規制

GHS分類

GHS ClassificationNot Classified

危険有害性情報

Hazard Classes and CategoriesNot Classified

毒性情報

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

安全データ

ridadr: 1760
毒性: 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

化学と産業

薬理情報

ATC Code · 3 件

S01EB09

S - Sensory organs

QS - Sensory organs

FDA Pharmacological Classification · 5 件

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 件

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

応用分野 · 5 件

解説アセチルコリン，コリンの酢酸エステルで，はじめて発見された神経伝達物質．バクテリア，動物，植物体に広く分布し，植物では麦角に，動物では脾臓，胎盤に高濃度に含まれる．トリメチルアミンと2-クロロエチルアセタートとの反応により合成される．遊離塩基は不安定であり，塩化物または臭化物として得られる．融点はおのおの151 ℃，143 ℃ で，いずれも潮解性である．水，エタノールに可溶，エーテルに不溶．生理的には運動神経と副交感神経の末端で分泌され，神経刺激の伝達に関与する．血圧降下，骨格筋収縮作用もある．生体内では，コリンとアセチルCoAからコリンアセチルトランスフェラーゼにより生合成され，エステラーゼによりすみやかに加水分解される．塩化物はLD50 170 mg/kg(マウス，皮下)．

説明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.

説明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.

使用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.

使用neurotransmitter (ester of choline and acetic acid)