5-ヒドロキシ-1H-インドール-3-エタンアミン
セロトニン · 3-(2-アミノエチル)-1H-インドール-5-オール · 5-ヒドロキシトリプタミン · DS物質 · トロムボシチン · トロンボシチン · 5-ヒドロキシ-1H-インドール-3-(エタンアミン) · アンテモビス
識別子と物理属性
| CAS No. | 50-67-9 |
|---|---|
| 分子式 | C10H12N2O |
| 平均分子量 | 176.21 g/mol |
| 単同位体質量 | 176.094963 g/mol |
| SMILES | NCCc1c[nH]c2ccc(O)cc12 |
| InChIKey | QZAYGJVTTNCVMB-UHFFFAOYSA-N |
| PubChem CID | 5202 |
| ChEMBL | CHEMBL39 |
| ChEBI | CHEBI:28790 |
| EC No. | 200-058-9 |
| DTXSID | DTXSID8075330 |
| 現地名 | 5-ヒドロキシ-1H-インドール-3-エタンアミン |
化学・物理的性質
| XLogP | 0.2 |
|---|---|
| 極性表面積 | 62 |
| 水素結合供与体数 | 3 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 2 |
| 重原子数 | 13 |
| 形式電荷 | 0 |
| 複雑度 | 174 |
| 医薬品 | Pharmaceuticals -> Listed in ZINC15 |
| SpringerMaterials Properties | Angular frequency |
| LogP（分配係数） | 0.21 |
| 溶解度 | 25.5 mg/mLChloroform (Slightly), DMSO (Slightly), Methanol (Slightly) |
| Physical Description | Solid |
| Ionization Efficiency | Positive2.352.7Agilent XCTElectrospray ionizationformic acid (5.3nM) |
| Collision Cross Section | 150.8 Ų [M+Na]+ [CCS Type: DTMethod: stepped-field]146.9 Ų [M+Na]+ [CCS Type: DTMethod: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]135.85 Ų [M-H]- [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)]139.08 Ų [M+Na]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]149.8 Ų [M+Na]+ |
| 融点 | 167.5 °C |
| 沸点 | 307.83°C (rough estimate) |
| 密度 | 1.1102 (rough estimate) |
| 屈折率 | 1.7110 (estimate) |
| 貯蔵条件 | 2-8°C |
| pKa（酸解離定数） | 9.8(at 25℃) |
| 外観・状態 | Solid |
| 色 | White to off-white |
| BRN | 143524 |
| 安定性 | Hygroscopic |
| InChI | InChI=1S/C10H12N2O/c11-4-3-7-6-12-10-2-1-8(13)5-9(7)10/h1-2,5-6,12-13H,3-4,11H2 |
| InChIKey | QZAYGJVTTNCVMB-UHFFFAOYSA-N |
| SMILES | N1C2=C(C=C(O)C=C2)C(CCN)=C1 |
| CAS データベース | 50-67-9(CAS DataBase Reference) |
| EPAの化学物質情報 | Serotonin (50-67-9) |
安全性と法規制
| GHS 分類 | DangerH301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]P203, P264, P270, P280, P301+P316, P318, P321, P330, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 67 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 3 (100%) |
| 水環境危害等級（WGK） | 3 |
| 輸送番号（UN） | UN 2811 6.1 / PGIII |
| 危険文句（R） | 63-25 |
| 危険表示 | T |
| 安全措置（S） | 36/37-45 |
| 危険等級 | IRRITANTAcute Tox. 3 OralRepr. 2 |
| 貯蔵分類 | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
用途
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.
使用
neurotransmitter