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(11E)-5β-アミノ-11-エチリデン-5,6,9,10-テトラヒドロ-7-メチル-5,9α-メタノシクロオクタ[b]ピリジン-2(1H)-オン

(11E)-5β-アミノ-11-エチリデン-5,6,9,10-テトラヒドロ-7-メチル-5,9α-メタノシクロオクタ[b]ピリジン-2(1H)-オン 化学構造式
102518-79-6
CAS番号.
102518-79-6
化学名:
(11E)-5β-アミノ-11-エチリデン-5,6,9,10-テトラヒドロ-7-メチル-5,9α-メタノシクロオクタ[b]ピリジン-2(1H)-オン
别名:
(11E)-5β-アミノ-11-エチリデン-5,6,9,10-テトラヒドロ-7-メチル-5,9α-メタノシクロオクタ[b]ピリジン-2(1H)-オン;(5R,11E)-5β-アミノ-11-エチリデン-5,6,9,10-テトラヒドロ-7-メチル-5α,9α-メタノシクロオクタ[b]ピリジン-2(1H)-オン;フペリジンA;(-)-フペルジンA;(±)-フペルジンA
英語化学名:
(-)-Huperzine A
英語别名:
HupA;Haboyin;Hupzine A;HUPERIZINE;Kimpukan A;Isoselagine;(-)-Selagine;Huperizine A;HUPERZINE A 1%;HUPERZINE A(P)
CBNumber:
CB9173024
化学式:
C15H18N2O
分子量:
242.32
MOL File:
102518-79-6.mol

(11E)-5β-アミノ-11-エチリデン-5,6,9,10-テトラヒドロ-7-メチル-5,9α-メタノシクロオクタ[b]ピリジン-2(1H)-オン 物理性質

融点 :
211-216oC
比旋光度 :
D -147° (c = 0.36 in CH3OH) (Ayer); D24.5 -150.4° (c = 0.498 in MeOH) (Liu)
沸点 :
505.0±50.0 °C(Predicted)
比重(密度) :
1.20±0.1 g/cm3(Predicted)
貯蔵温度 :
Keep in dark place,Inert atmosphere,2-8°C
酸解離定数(Pka):
12.25±0.60(Predicted)
外見 :
neat
光学活性 (optical activity):
[α]/D -153±5°, c = 0.5 in methanol
CAS データベース:
102518-79-6(CAS DataBase Reference)
安全性情報
  • リスクと安全性に関する声明
  • 危険有害性情報のコード(GHS)
主な危険性  T+
Rフレーズ  26/27/28-36/37/38
Sフレーズ  26-36/37/39-45
RIDADR  UN 1544 6.1/PG 2
WGK Germany  3
RTECS 番号 PB9185700
HSコード  29339900
絵表示(GHS)
注意喚起語 Danger
危険有害性情報
コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード
H300 飲み込むと生命に危険 急性毒性、経口 1, 2 危険 P264, P270, P301+P310, P321, P330,P405, P501
注意書き

(11E)-5β-アミノ-11-エチリデン-5,6,9,10-テトラヒドロ-7-メチル-5,9α-メタノシクロオクタ[b]ピリジン-2(1H)-オン 価格 もっと(23)

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
富士フイルム和光純薬株式会社(wako) W01CHDASB-00008340 フペルジンA
Huperzine A
102518-79-6 5mg ¥19600 2021-03-23 購入
富士フイルム和光純薬株式会社(wako) W01CHDASB-00008340 フペルジンA
Huperzine A
102518-79-6 10mg ¥35200 2021-03-23 購入
東京化成工業 H1700 (-)-フペルジンA >98.0%(HPLC)
(-)-Huperzine A >98.0%(HPLC)
102518-79-6 10mg ¥15000 2021-03-23 購入
東京化成工業 H1700 (-)-フペルジンA >98.0%(HPLC)
(-)-Huperzine A >98.0%(HPLC)
102518-79-6 100mg ¥86000 2021-03-23 購入
関東化学株式会社(KANTO) 49064-32 フペルジンA
Huperzine A
102518-79-6 10mg ¥46000 2021-03-23 購入

(11E)-5β-アミノ-11-エチリデン-5,6,9,10-テトラヒドロ-7-メチル-5,9α-メタノシクロオクタ[b]ピリジン-2(1H)-オン 化学特性,用途語,生産方法

外観

白色~ほとんど白色粉末~結晶

用途

フペルジンA (ヒューペルジンA、Huperzine A) はトウゲシバ (Huperzia serrata) に含まれるアルカロイド。 フペルジンAは、ドネペジルやリバスチグミン (Rivastigmine)、ガランタミン (Galantamine) と同様にアセチルコリンエステラーゼ阻害剤である。 アメリカ合衆国では、フペルジンAは記憶支援のための栄養補助食品(サプリメント)として販売されている。フペルジンAを含む植物は、中国において古くから腫れ、発熱、血液疾患の治療に用いられてきた。中国における臨床試験において、本化合物がアルツハイマー病の治療に効果があることが示されている他、健康な若い学生を対象とした試験で、一回の学習において記憶力を増強させることが明らかにされている。

説明

Huperzine A is obtained from Huperzia serrata, which is the perennial fern. It shows activities in antipyretic, hemostasis, and dehumidification and is used for the treatment in folk of pneumonia, lung abscess, hematemesis, hematochezia, traumatic injury, etc.

化学的特性

Pale Brown Solid

物理的性質

Appearance: white crystalline powder. Bitter with hygroscopicity. Solubility: easily soluble in chloroform, soluble in methanol and ethanol, and slightly soluble in water. Melting point: 211–216?°C.

来歴

In the 1980s, Chinese scholars isolated huperzine A from Lycopodiales, Huperziaceae, Phlegmariurus fordii, and Huperzia serrata (Thunb.) Trevis. At present, about 120 chemical components have been isolated and identified from the plant, including 90 lycopodium alkaloids and 32 lycopodium triterpenes. Huperzine A has the most potent inhibition on acetylcholinesterase activity, followed by huperzine B and 6β-hydroxy huperzine A.?These three compounds belong to lycodine-type lycopodium alkaloids. The full synthesis of huperzine A is complex and costly. Therefore, it is a focus to develop biotransformation or semisynthesis with other alkaloids as lead compounds on the basis of the intrinsic relationship among different kinds of alkaloids
After the determination of chemical structure of huperzine A in 1986, it was found to be the same alkaloid as selagine separated from Lycopodium selago by Valenta in the 1960s, so it was classified as lycodine-type alkaloid. Huperzine A is a potent reversible inhibitor of AChE, and its ability to improve learning and memory has been validated in animal models. It was approved for treatment in Alzheimer’s disease (AD) in China in 1996
Due to the high cost of extraction of huperzine A, research on its chemical synthesis has been the focus at home and abroad since 1986. It has been found that the chiral structure of huperzine A is essential for its biological activity; the inhibitory activity on AChE of natural products (-)?- huperzine A is twice as its raceme and 38–50 times as its enantiomer (+)?- huperzine A which is not a natural product, so the chemical synthesis of natural product (-)?- huperzine A has received extensive attention. The chemical preparation method of (-)?- huperzine A can be divided into asymmetric synthesis and raceme separation and is limited to a small amount preparation in laboratory for the high cost.
Considering the difficulty of realizing unique bridge ring and amino structure of (-)?- huperzine A and achieving its full synthesis and structural modification, scientists are trying to synthesize analogues of huperzine A with simple structure and AchE inhibitory activity. It was found that the activity of spearmint huperzine A was similar to that of huperzine A, with improved selectivity and poor chemical stability. It was modified structurally to obtain ZT-1 .

使用

Reversible alkaloid inhibitor of AChE which crosses the blood-brain barrier. A potential therapeutic agent for Alzheimer disease. It reduces cell death induced by glutamate in primary cultures derived from forebrain, hippocampus, cortex and cere

使用

anticholinesterase, cognition enhancer

使用

cognition-enhancing activity, potential Alzheimer’s therapeutic

定義

ChEBI: A sesquiterpene alkaloid isolated from a club moss Huperzia serrata that has been shown to exhibit neuroprotective activity.

適応症

It was mainly applied to age-related memory dysfunction and Alzheimer and has a good effect on improving memory function. It can be used to treat various types of Alzheimer’s disease and also myasthenia gravis.

薬理学

Huperzine A has the ability to enhance learning and memory, improve spatial memory, and can be used for age-related dementia, vascular dementia, and other neurodegenerative diseases. Compared with the current anti-AD drugs, huperzine A can go through the blood-brain barrier, with a high oral bioavailability and longer time inhibition on AChE.
As a highly selective AChE reversible inhibitor, huperzine A can inhibit AChE, reduce acetylcholine hydrolysis, and improve the level of acetylcholine in the synaptic gap. This inhibition is reversible, lasts for a long time, shows no drug dependence if repeated administration, and does not induce significant liver toxicity. X-ray diffraction results show that the direct binding of huperzine A to AChE active sites inhibits the binding of AChE to its substrate.
In addition to the potent inhibition on AChE, huperzine A only shows a weak inhibitory effect on the butyrylcholinesterase; also protects neurons by inhibiting oxidative stress, reducing somatostatin, reducing the content of glutamate, decreasing the increased intracellular calcium, and inhibiting neuronal apoptosis; further improves AD-related cognitive function and reduces the symptoms of AD patients.

臨床応用

Since 1994, huperzine A has been approved for clinical use in improving memory and cognitive impairment in old patients with memory loss and dementia. A large number of domestic clinical studies have found that huperzine A shows therapeutic effect on learning and cognitive dysfunction of vascular dementia, mental retardation, and schizophrenia patients with mild adverse reactions.

(11E)-5β-アミノ-11-エチリデン-5,6,9,10-テトラヒドロ-7-メチル-5,9α-メタノシクロオクタ[b]ピリジン-2(1H)-オン 上流と下流の製品情報

原材料

準備製品


(11E)-5β-アミノ-11-エチリデン-5,6,9,10-テトラヒドロ-7-メチル-5,9α-メタノシクロオクタ[b]ピリジン-2(1H)-オン 生産企業

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102518-79-6((11E)-5β-アミノ-11-エチリデン-5,6,9,10-テトラヒドロ-7-メチル-5,9α-メタノシクロオクタ[b]ピリジン-2(1H)-オン)キーワード:


  • 102518-79-6
  • Huperzine-A1-5%
  • (5r-(5-alpha,9-beta,11e))-ydro-7-methyl
  • 5,9-methanocycloocta(b)pyridin-2(1h)-one,5-amino-11-ethylidene-5,6,9,10-tetrah
  • HUPERIZINE
  • (-)-HUPERZINE A FROM HUPERZIA SERRATA
  • HuperziaSerrateP.E120786-18-7/
  • (5R,9R,E)-5-AMino-11-ethylidene-7-Methyl-5,6,9,10-tetrahydro-5,9-Methanocycloocta[b]pyridin-2(1H)-one
  • (-)-Huperzine A (HupA)
  • Huperzine Serrate Extract
  • (-)-Huperzine A (HupA) (-)-Selagine
  • Haboyin
  • (1R,9S,13E)- 1-AMINO- 13-ETHYLIDENE- 11-METHYL- 6-AZATRICYCLO[7.3.1.02,7] TRIDECA- 2(7),3,10- TRIEN- 5-ONE
  • Huperzine A, 98%, from Huperzia serrata (Thunb.) Trevis.
  • Huperzia Serrate P.E./Huperzine-A
  • (-)-HUPERZINE A (HUPERZINE A)
  • Huperzine A 102518-79-6
  • (+-)-huperzine A,Huperzine-a,Huperzine A
  • HUP, [5R-(5a,911E)]-5-Amino-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-5,9-methanocycloocta[b]pyridin-2-(1H)-one, Selagine,
  • 5,9-Methanocyclooctabpyridin-2(1H)-one, 5-amino-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-, (5R,9R,11E)-
  • HUPERZINE A 1%
  • Huperzine A ( Selagine )
  • (-)-HUPERZINE A, 99% HPLC
  • (-)-Huperzine A
  • (-)-Selagine
  • [5R-(5α,9β,11E)]-5-Amino-11-ethylidene-
  • 5,6,9,10-tetrahydro-7-methyl-5,9-methanocycloocta[b]pyridin-2(1H)-one
  • (5R,11E)-5β-Amino-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-5α,9α-methanocycloocta[b]pyridin-2(1H)-one
  • Huperizine A
  • Kimpukan A
  • SynonyMs (-)-Selagine
  • (11E)-5β-アミノ-11-エチリデン-5,6,9,10-テトラヒドロ-7-メチル-5,9α-メタノシクロオクタ[b]ピリジン-2(1H)-オン
  • (5R,11E)-5β-アミノ-11-エチリデン-5,6,9,10-テトラヒドロ-7-メチル-5α,9α-メタノシクロオクタ[b]ピリジン-2(1H)-オン
  • フペリジンA
  • (-)-フペルジンA
  • (±)-フペルジンA
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