アセチルコリン

アセチルコリン 化学構造式
51-84-3
CAS番号.
51-84-3
化学名:
アセチルコリン
别名:
アセチルコリン;(2-アセトキシエチル)トリメチルアンモニウム
英語名:
Acetylcholine
英語别名:
ACETYLECHOLINE;O-Acetylcholine;(2-acetoxyethyl)trimethylammonium;Acetylcholine;2-acetyloxyethyl-trimethyl-ammonium;2-Acetoxy-N,N,N-trimethylethan-1-aminium;(2-acetoxyethyl)trimethylammonium USP/EP/BP;Ethanaminium,2-(acetyloxy)-N,N,N-trimethyl-;AcetylcholineQ: What is Acetylcholine Q: What is the CAS Number of Acetylcholine
CBNumber:
CB0895802
化学式:
C7H16NO2+
分子量:
146.21
MOL File:
51-84-3.mol

アセチルコリン 物理性質

沸点 :
265.84°C (rough estimate)
比重(密度) :
1.0528 (rough estimate)
屈折率 :
1.4500 (estimate)
CAS データベース:
51-84-3
EPAの化学物質情報:
Acetylcholine (51-84-3)

安全性情報

RIDADR  1760
国連危険物分類  8
容器等級  II
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.

アセチルコリン 価格

メーカー 製品番号 製品説明 CAS番号 包装 価格 更新時間 購入

アセチルコリン 化学特性,用途語,生産方法

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

neurotransmitter (ester of choline and acetic acid)

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.

作用機序

コリン作動性神経や神経筋接合部における神経伝導の化学伝達物質。神経興奮時に神経終末から遊離し,シナプス後膜に作用する。化学伝達物質にはほかにノルアドレナリンがあり,自律神経系を機能的にコリン作動性神経とアドレナリン作動性神経に分類することができる。アセチルコリンはコリンと酢酸から生成される。コリンエステラーゼによりすぐに分解されるので,作用が一過性であり,治療薬としてはあまり用いられない。抗コリンエステラーゼ剤を用いれば,作用は増強し,延長する。類似の化合物で作用が長く持続するメサコリン (メコリール) ,カルバコール (カルコリン) ,ベタネコール (ベサコリン) が,末梢血管の循環障害,手術後の腸管麻痺,膀胱麻痺による排尿障害などの治療に用いられる。

生物学の機能

The discovery that ACh was a transmitter in the peripheral nervous system formed the basis for the theory of neurotransmission. ACh is also a neurotransmitter in the mammalian brain; however, only a few cholinergic tracts have been clearly delineated.ACh is an excitatory neurotransmitter in the mammalian CNS.There is good evidence that ACh (among other neurotransmitters) is decreased in certain cognitive disorders, such as Alzheimer’s disease.

作用機序

Acetylcholine functions primarily as a chemical neurotransmitter in the nervous systems of all animals. When a cholinergic neuron is excited, it releases transmitter into the synaptic cleft where it can bind to a number of different receptor proteins. The receptors for acetylcholine can be classified into two general categories based primarily on the actions of different plant alkaloids that affect their function: nicotinic (nicotine binding) or muscarinic (muscarine binding). Several different subtypes for each of these general receptor classes have been characterized. The receptor binding event can be transduced into opening of cationic or anionic ion channels or coupled to some other metabolic signal such as phospholipid turnover rates or activation of second-messenger systems. Both inhibitory or, more commonly, excitatory responses are induced in the neurons or effector cells which receive the neurotransmitter signal, making acetylcholine-mediated neurotransmission particularly versatile.
In addition to the ubiquitous presence of acetylcholine in the nervous systems of all animals, it is also found in a limited number of plants, bacteria, fungi and protozoa. This widespread distribution in a variety of species most likely indicates the appearance of acetylcholine-metabolizing proteins fairly early in evolutionary history. In vertebrates, acetylcholine is also found in non-neuronal tissues such as primate placenta and sperm where its functional role, if any, remains unknown.

臨床応用

The cholinergic system was the first neurotransmitter system shown to have a role in wakefulness and initiation of REM sleep. Because of the poor penetration of the cholinergic drugs into the CNS, the role of this system in sleep has relied on animal studies using microinjection into the brain, primarily in the area of the dorsal pontine tegmentum. Acetylcholine, cholinergic agonists (e.g., arecoline or bethanechol), and cholinesterase inhibitors are effective in the initiation of REM sleep from NREM sleep after microinjection. Conversely, administration of anticholinergic drugs (e.g., atropine or scopolamine) hinders the transition to REM sleep. Increase in the rate of discharge of these cholinergic cells (that activate the thalamus, cerebral cortex, and hippocampus) during REM sleep parallel the same pattern seen with arousal and alertness.

合成

Acetylcholine, 2-acetoxy-N,N,N-trimethylethyl ammonium chloride (13.1.2), is easily synthesized in a number of different ways. For example, 2-chloroethanol is reacted with trimethylamine, and the resulting N,N,N-trimethylethyl-2-ethanolamine hydrochloride (13.1.1), also called choline, is acetylated by acetic acid anhydride or acetylchloride, giving acetylcholine (13.1.2). A second method consists of reacting trimethylamine with ethylene oxide, giving N,N,N-trimethylethyl-2-ethanolamine hydroxide (13.1.3), which upon reaction with hydrogen chloride changes into the hydrochloride (13.1.1), which is further acetylated in the manner described above. Finally, acetylcholine is also formed by reacting 2-chloroethanol acetate with trimethylamine [1¨C7].

Synthesis_51-84-3

環境運命予測

Cholinergic agents can increase the acetylcholine level at the synaptic junction and cause rapid firing of the postsynaptic membrane. Antiacetylcholinesterase agents block the acetylcholinesterase enzyme and thus increase the acetylcholine level in the synapse causing rapid firing of the postsynaptic membrane.

代謝

Acetylcholine in the synapse can bind with cholinergic receptors on the postsynaptic or presynaptic membranes to produce a response. Free acetylcholine that is not bound to a receptor is hydrolyzed by AChE. This hydrolysis is the physiologic mechanism for terminating the action of acetylcholine. Enough AChE is present in the synapse to hydrolyze approximately 3 × 108 molecules of acetylcholine in 1 millisecond; thus, adequate enzyme activity exists to hydrolyze all the acetylcholine (~3 × 106 molecules) released by one action potential. A number of useful therapeutic cholinomimetic agents have been developed based on the ability of the compounds to inhibit AChE; these agents are addressed later in this chapter.

アセチルコリン 上流と下流の製品情報

原材料

準備製品


アセチルコリン 生産企業

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51-84-3(アセチルコリン)キーワード:


  • 51-84-3
  • 2-acetyloxyethyl-trimethyl-ammonium
  • Acetylcholine
  • Ethanaminium,2-(acetyloxy)-N,N,N-trimethyl-
  • (2-acetoxyethyl)trimethylammonium USP/EP/BP
  • AcetylcholineQ: What is Acetylcholine Q: What is the CAS Number of Acetylcholine
  • ACETYLECHOLINE
  • (2-acetoxyethyl)trimethylammonium
  • O-Acetylcholine
  • 2-Acetoxy-N,N,N-trimethylethan-1-aminium
  • アセチルコリン
  • (2-アセトキシエチル)トリメチルアンモニウム
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