基本情報
- 標準SMILES
NC12CC3CC(CC(C3)C1)C2- InChIKey
DKNWSYNQZKUICI-UHFFFAOYSA-N- 分子式
- C10H17N
- 平均分子量
- 151.25 g/mol
- 単同位体質量
- 151.13609955
名称と識別子
- 優先名称
- Amantadine
- IUPAC
- adamantan-1-amine
- 現地名
- (1-アダマンチル)アミン
- 英語名
- Amantadine
- 分子式
- C10H17N
- 分子量
- 151.25
名称と別名
名称をさらに表示
データベース識別子
- CAS
768-94-5- PubChem CID
- 2130
- DTXSID
DTXSID8022117- ChEMBL
CHEMBL660- ChEBI
CHEBI:2618- UNII
- BF4C9Z1J53
- EC Number
- 212-201-2
- Nikkaji
- J6.971J
物性
構造計算による物性
- XLogP
- 2.4
- 極性表面積
- 26 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 1
- 回転可能結合数
- 0
- 重原子数
- 11
- 形式電荷
- 0
- 複雑度
- 144
物理化学的性質
- 融点
- 206 · 206-208 °C(lit.)
- 沸点
- 263.29 °C · 263.29°C (rough estimate)
- 比重(密度)
- 0.951 · 0.9510 (rough estimate)
- 屈折率
- 1.522 · 1.5220 (estimate)
- 貯蔵温度
- Keep in dark place,Inert atmosphere,Room temperature
- 溶解性
- 5 %、透明からかすんだ、無色からかすかな黄色または黄褐色 · M HCl: 可溶5%、透明からかすんだ、無色からかすかな黄色または黄褐色
- 外見
- 粉
- 酸解離定数(Pka)
- 10.1 · 10.1(at 25℃)
- 色
- ホワイト~クリーム
- 水溶解度
- 有機溶剤に可溶。水に不溶。
- Merck
- 14 · 14,374
- BRN
- 2204333 · 2204333
- 主な用途
- 食品および飲料パーソナルケア医薬品
- InChI
- 1S/C10H17N/c11-10-4-7-1-8(5-10)3-9(2-7)6-10/h7-9H,1-6,11H2/t7-,8+,9-,10-
- InChIKey
- DKNWSYNQZKUICI-UHFFFAOYSA-N
- SMILES
- NC12C[C@H]3C[C@H](C[C@H](C3)C1)C2
- CAS データベース
- 768 · 768-94-5(CAS DataBase Reference)
- NISTの化学物質情報
- 3.3 · Tricyclo[3.3.1.13,7]decane-1-amine(768-94-5)
- EPAの化学物質情報
- 3.3 · Tricyclo[3.3.1.13,7]decan-1-amine (768-94-5)
化学的性質
化学的特性White to cream powder
安全と法規制
安全データ
- F
- 10-34
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- YD1925000
- 毒性
- LD50 oral in rat: 900mg/kg
- hs_code
- 29213000
- risk_code
- 22-36/37/38
- hazard_code
- Xn,Xi
- safety_code
- 26-36
- Hazard Classifications
- Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
- ストレージクラス
- 11 - Combustible Solids
- 有毒物質データの
- 768-94-5(Hazardous Substances Data)
化学と産業
応用分野
用途アマンタジン (Amantadine) は、アダマンタンにアミノ基がついた構造をしているアミンの一種である。NMDA受容体を拮抗阻害作用がある。パーキンソン病やA型インフルエンザの治療に使われている。製品名はシンメトレル。
説明Amantadine is an agent that raises the concentration of dopamine in the synaptic cleft by releasing it from neurons and suppressing the process of reuptake.
使用Amantadine is a primary amine derivative of adamantane. It has an effect on mycoviruses, which are RNA-containing viruses. It has a very narrow spectrum of action and is used only for treating and preventing influenza A. It is also used for treating Parkinsonism. The exact mechanism of antiviral action of amantadine is not completely understood. It is believed that it is an ion channel blocker. It has also been suggested that amantadine inhibits absorption of viral particles into the host cell, which is expressed in the breakdown of diffusion of the virus into the cell, or inhibition of the “stripping process” of the virus. The main use is for the prevention of type A2 influenza. Synonyms of this drug are simmetrel, viregit, mantadan, and others.
一般的な説明Amantadine has been used for years as a treatment for Parkinson disease. The adamantanamines have twomechanisms in common:they inhibit an early step in viralreplication, most likely viral uncoating,and in somestrains, they affect a later step that probably involves viral assembly,possibly by interfering with hemagglutinin processing.The main biochemical locus of action is the influenzatype A virus M2 protein, which is an integral membrane proteinthat functions as an ion channel. The M2 channel is a protontransport system. By interfering with the function of theM2 protein, the adamantanamines inhibit acid-mediated dissociationof the ribonucleoprotein complex early in replication.They also interfere with transmembrane proton pumping,maintaining a high intracellular proton concentrationrelative to the extracellular concentration and enhancingacidic pH-induced conformational changes in the hemagglutininduring its intracellular transport at a later stage. The conformationalchanges in hemagglutinin prevent transfer of thenascent virus particles to the cell membrane for exocytosis.
調製方法
純化方法Dissolve the amine in Et2O, dry it over KOH, evaporate and sublime it in vacuo. [Stetter et al. Chem Ber 93 226 1960.]
上流・下流製品情報
上流原料
下流製品
サプライヤー50 社
補足説明
定義ChEBI: A member of the class of adamantanes that is used as an antiviral and antiparkinson drug.
関連反応
関連ノート
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