5-ヒドロキシ-1H-インドール-3-エタンアミン

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）

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.