5-ヒドロキシ-1H-インドール-3-エタンアミン 化学特性,用途語,生産方法
外観
わずかにうすい褐色～褐色、結晶～結晶性粉末
解説
5-hydroxytryptamine．C10H12N2O(176.22)．ほ乳動物の腸，血小板，および中枢神経に分布する生理学的に重要なアミノ酸の一種．バナナ，アボカド，ナス，トマト，クルミなどの植物にも存在している．トリプトファンから生合成され，生体内ではクレアチン硫酸との錯体として存在する．トリプトファンの代謝産物。哺乳(ほにゅう)類の血小板，血清，胃粘膜，頭足類の唾液(だえき)腺などに含まれ，血管・平滑筋収縮の作用をもつ。脳神経のシナプス小胞に大量に含まれ，中枢神経シナプスの刺激伝達物質と考えられている。セロトニンほ乳動物の消化器系，血管系，呼吸器系，神経系に対して多様な役割を担うことが知られている．たとえば，視床下部への神経伝達，血管の収縮，平滑筋収縮のような作用を示す．融点167～168 ℃(塩酸塩)，215 ℃(クレアチン硫酸との錯体)．pKa1 9.69±0.40，pKa2 10.31±0.10．森北出版「化学辞典（第2版）
生理作用
必須アミノ酸のトリプトファンが体内で代謝される過程で生合成される化学伝達物質（神経伝達物質）。哺乳(ほにゅう)動物では、血小板中や小腸粘膜および脳神経系に存在する。多くは小腸粘膜にある腸クロム親和性細胞（EC：enterochromaffin cell）に存在し、腸の蠕動(ぜんどう)運動をはじめ消化管の働きにかかわる。消化管でセロトニンが過剰に分泌されると下痢に、不足すれば便秘となり、こうした便通異常のほか腹痛や腹部の不快感を伴う過敏性腸症候群の症状にも関与する。血中のセロトニンは血小板に取り込まれて体内をめぐり、血液を凝固させ血小板血栓を形成する血液凝固作用（止血作用）や血管収縮作用などを示す。血管収縮作用に関して、脳血管が収縮したのち拡張すると片頭痛がおこるともされるが、片頭痛の原因には諸説が多い。
脳神経系に存在するセロトニンは、うつの原因ともされるドーパミン不足の調節に関与し、心身を安定させるように働く。したがって、ストレスなどが原因でセロトニン不足が生じると精神の安定が保てず、うつ病や不眠症などになる。また、睡眠のほか、生体リズムや体温調節などにもかかわっている。［編集部］
用途
薬理研究、有機合成原料。
説明
Serotonin is the baby boomer of neurotransmitters: It was identified in the late 1940s, its adolescence was troubled and turbulent, it made the drug scene in the 1960s, and it nearly died of an overdose in the early 1970s. At one point, the remark was made that serotonin doesn't do anything. On reaching its middle years, serotonin has matured and become an important topic of study, a household name, and more complicated than ever. Serotonin has been associated with, among other things, anxiety, depression, schizophrenia, drug abuse, sleep, dreaming, hallucinogenic activity, headache, cardiovascular disorders, and appetite control, and it is now dabbling in acupuncture and transcendental meditation.
Serotonin was independently identified in the late 1940s by two groups of investigators: In the United States, it was called serotonin, whereas in Italy, it was
called enteramine. Its total synthesis in the early 1950s confirmed that both substances were 5-hydroxytryptamine (5-HT ). Serotonin (5-HT ) was detected in
numerous plant and animal species and, in the mid-1950s, was identified in the central nervous system (CNS) of animals. A neurotransmitter role was
subsequently proposed for this substance. Later, 5-HT was implicated in a variety of central and peripheral physiologic actions. It seemed to be involved in
vasoconstriction and vasodilation, regulation of body temperature, sleep, and hormonal regulation, and evidence suggested that it might be involved in
depression. The structural similarity between 5-HT and the then recently discovered hallucinogenic agent (+)-lysergic acid diethylamide (LSD) intrigued
investigators. This observation led to speculation that 5-HT might be involved in the mechanism of action of psychoactive substances and that it might play a
seminal role in various mental disorders.
使用
neurotransmitter
定義
ChEBI: A primary amino compound that is the 5-hydroxy derivative of tryptamine.
生物学の機能
Serotonin (5-hydroxytryptamine, or 5HT) is present in
the brain as well as in the periphery. In humans, about
90% of the total serotonin in the body is in enterochromaffin
cells in the gastrointestinal tract; the remaining
10% occurs primarily in the platelets and brain. The
physiological significance of the vast amounts of serotonin
constantly synthesized and metabolized in the periphery
still remains an enigma. Brain serotonin has been
implicated as a potential neurotransmitter in the mediation
of a wide variety of phenomena.
臨床応用
Initially, serotonin was thought to be a sleep-promoting neurotransmitter or an “antiwaking” agent. The
recognition of the numerous 5-HT receptor subtypes, often with unique anatomical distribution, has required
that a more complex role for serotonin be developed. Current studies indicate that conditions for sleep are now
met when the serotoninergic system becomes inactive. The serotonin agonists for the 5-HT1 (via the 5-HT1A
and 5-HT1B types at the hypothalamic level), 5-HT2, and 5-HT3 receptors cause wakefulness and inhibit sleep.
Blockade of the 5-HT2 receptors (e.g., the 5-HT2 antagonist ritanserin) results in increased NREM sleep and
inhibition of REM sleep. It has been proposed that the 5-HT1A and 5- HT2 may be involved in sleep by
regulation of sleep-promoting substances in the hypothalamus. With the development of newer and more
selective ligands for use in studying the numerous serotonin receptor subtypes, a better
understanding of the role of serotonin in sleep will evolve.
代謝
The major route of metabolism for 5-HT is oxidative deamination by monoamine oxidase (MAO-A) to the unstable 5-hydroxyindole- 3-acetaldehyde, which is either reduced to 5-hydroxytryptophol (~15%) or oxidized to 5-hydroxyindole-3-acetic acid (~85%). In the pineal gland, 5-HT is acetylated by 5-HT N-acetyltransferase to N-acetylserotonin, which undergoes O-methylation by 5-hydroxyindole-O-methyltransferase to melatonin.
参考文献
Petrova, Men'shikov,J. Gen. Chern. USSR, 31,2413 (1961)
5-ヒドロキシ-1H-インドール-3-エタンアミン 上流と下流の製品情報
原材料
準備製品