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(-)-Huperzine A

(-)-Huperzine A 구조식 이미지
카스 번호:
102518-79-6
상품명:
(-)-Huperzine A
동의어(영문):
HupA;Haboyin;Hupzine A;HUPERIZINE;Kimpukan A;Isoselagine;(-)-Selagine;Huperizine A;HUPERZINE A 1%;HUPERZINE A(P)
CBNumber:
CB9173024
분자식:
C15H18N2O
포뮬러 무게:
242.32
MOL 파일:
102518-79-6.mol

(-)-Huperzine A 속성

녹는점
211-216oC
알파
D -147° (c = 0.36 in CH3OH) (Ayer); D24.5 -150.4° (c = 0.498 in MeOH) (Liu)
끓는 점
505.0±50.0 °C(Predicted)
밀도
1.20±0.1 g/cm3(Predicted)
저장 조건
Keep in dark place,Inert atmosphere,2-8°C
산도 계수 (pKa)
12.25±0.60(Predicted)
물리적 상태
neat
optical activity
[α]/D -153±5°, c = 0.5 in methanol
CAS 데이터베이스
102518-79-6(CAS DataBase Reference)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 T+
위험 카페고리 넘버 26/27/28-36/37/38
안전지침서 26-36/37/39-45
유엔번호(UN No.) UN 1544 6.1/PG 2
WGK 독일 3
RTECS 번호 PB9185700
HS 번호 29339900
그림문자(GHS):
신호 어: Danger
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H300 삼키면 치명적임 급성 독성 물질 - 경구 구분 1,2 위험 P264, P270, P301+P310, P321, P330,P405, P501
예방조치문구:

(-)-Huperzine A C화학적 특성, 용도, 생산

개요

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.

개요

(?)-Huperzine A is a natural sesquiterpene alkaloid first isolated from Huperzia, a club moss used in Chinese medicine for its neuroprotective activity. It inhibits acetylcholinesterase (AChE) in rat cortex in vitro (IC50 = 82 nM) and displays oral AChE inhibitory activity in animals. (?)-Huperzine A has potential applications in a variety of neuroprotective roles, including protection against organophosphate nerve agents and ameliorating symptoms of Alzheimer’s disease.

화학적 성질

Pale Brown Solid

물리적 성질

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.

역사

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 .

용도

anticholinesterase, cognition enhancer

용도

cognition-enhancing activity, potential Alzheimer’s therapeutic

용도

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

정의

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

Indications

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.

Pharmacology

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.

Clinical Use

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.

(-)-Huperzine A 준비 용품 및 원자재

원자재

준비 용품


(-)-Huperzine A 공급 업체

글로벌( 427)공급 업체
공급자 전화 팩스 이메일 국가 제품 수 이점
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com China 22607 55
Hangzhou FandaChem Co.,Ltd.
008615858145714
+86-571-56059825 fandachem@gmail.com CHINA 9128 55
ATK CHEMICAL COMPANY LIMITED
+86 21 5161 9050/ 5187 7795
+86 21 5161 9052/ 5187 7796 ivan@atkchemical.com CHINA 26782 60
Shanghai Zheyan Biotech Co., Ltd.
18017610038
zheyansh@163.com CHINA 3623 58
career henan chemical co
+86-0371-55982848
sales@coreychem.com China 29954 58
Chengdu Biopurify Phytochemicals Ltd.
18482058008 18080483897
maggie@biopurify.com China 2712 58
Cangzhou Wanyou New Material Technology Co.,Ltd
18631714998
sales@czwytech.com CHINA 914 58
hdzhl biotechnology co., ltd
86-13032617415
sales@luchibiology.com CHINA 1275 58
Chongqing Chemdad Co.,Ltd
+86-19923101450
sales@chemdad.com CHINA 4000 58
Xi'an Kono chem co., Ltd.,
13289246953 029-86107037
info@konochemical.com CHINA 3000 58

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