(-)-Huperzine A

Names

[ Name ]:
(-)-Huperzine A

[Synonym ]:
5-Amino-1,2-dihydro-3H-pyrazol-3-one
(−)-Huperzine A
MFCD01714949
(−)-Selagine
(-)-Huperzine A
3-Amino-5-pyrazolone
3-Amino-1H-pyrazol-5-ol
3H-Pyrazol-3-one, 5-amino-1,2-dihydro-
Huperzine A

Biological Activity

[Description]:

Huperzine A, an active Lycopodium alkaloid extracted from traditional Chinese herb, is a potent, selective and reversible acetylcholinesterase (AChE) inhibitor and has been widely used in China for the treatment of Alzheimer's disease (AD). IC50 value:Target: AChEHuperzine A exhibited protective effects against d-gal-induced hepatotoxicity and inflamm-aging by inhibiting AChE activity and via the activation of the cholinergic anti-inflammatory pathway. The huperzine A mechanism might be involved in the inhibition of DAMPs-mediated NF-κB nuclear localization and activation. Huperzine A is a potential therapeutic agent for Alzheimer's disease.

[Related Catalog]:

Signaling Pathways >> Neuronal Signaling >> AChE

Natural Products >> Alkaloid

Research Areas >> Neurological Disease

[References]

[1]. Burshtein G, Friedman M, Greenberg S, Hoffman A. Transepithelial Transport of a Natural Cholinesterase Inhibitor, Huperzine A, along the Gastrointestinal Tract: the Role of Ionization on Absorption Mechanism. Planta Med. 2013 Jan 23.

[2]. Ruan Q, Liu F, Gao Z, et al. The anti-inflamm-aging and hepatoprotective effects of huperzine A in d-galactose-treated rats. Mech Ageing Dev. 2013 Jan 8. pii: S0047-6374(12)00182-0.

[3]. Zhang HY. New insights into huperzine A for the treatment of Alzheimer's disease. Acta Pharmacol Sin. 2012 Sep;33(9):1170-5.

[4]. Wang J, Zhang HY, Tang XC. Huperzine a improves chronic inflammation and cognitive decline in rats with cerebral hypoperfusion. J Neurosci Res. 2010 Mar;88(4):807-15. doi: 10.1002/jnr.22237.

[5]. Park P, Schachter S, Yaksh T. Intrathecal huperzine A increases thermal escape latency and decreases flinching behavior in the formalin test in rats. Neurosci Lett. 2010 Feb 5;470(1):6-9. doi: 10.1016/j.neulet.2009.12.033.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
479.5±25.0 °C at 760 mmHg

[ Melting Point ]:
211-216oC

[ Molecular Formula ]:
C₁₅H₁₈N₂O

[ Molecular Weight ]:
242.32

[ Flash Point ]:
243.8±23.2 °C

[ PSA ]:
58.88000

[ LogP ]:
-0.22

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.741

[ Storage condition ]:
−20°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: PB9185700

CHEMICAL NAME :: 5,9-Methanocycloocta(b)pyridin-2(1H)-one, 5-amino-11-ethylidene-5,6,9,10-tetrahydro-7- methyl-, (5R-(5-alpha,9-beta,11E))-

CAS REGISTRY NUMBER :: 102518-79-6

LAST UPDATED :: 199706

DATA ITEMS CITED :: 8

MOLECULAR FORMULA :: C15-H18-N2-O

MOLECULAR WEIGHT :: 242.35

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 15 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ZYYZEW Zhongguo Yaolixue Yu Dulixue Zazhi. (Chinese Pharmacological Society, 27 Tai-Ping Road, Beijing 100850, China) V.1- 1986- Volume(issue)/page/year: 3,246,1989

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2472 ug/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - lacrimation Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory depression

REFERENCE :: CYLPDN Zhongguo Yaoli Xuebao. Acta Pharmacologica Sinica. Chinese Journal of Pharmacology. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1980- Volume(issue)/page/year: 8,117,1987

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2500 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #5177082

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 5200 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #5177082

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1793 ug/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - lacrimation Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory depression

REFERENCE :: CYLPDN Zhongguo Yaoli Xuebao. Acta Pharmacologica Sinica. Chinese Journal of Pharmacology. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1980- Volume(issue)/page/year: 8,117,1987

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #5177082

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 630 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #5177082

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 1200 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ZYYZEW Zhongguo Yaolixue Yu Dulixue Zazhi. (Chinese Pharmacological Society, 27 Tai-Ping Road, Beijing 100850, China) V.1- 1986- Volume(issue)/page/year: 3,246,1989

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H300 + H310 + H330-H315-H319-H335

[ Precautionary Statements ]:
P260-P264-P280-P284-P301 + P310-P302 + P350

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
T+

[ Risk Phrases ]:
R26/27/28;R36/37/38

[ Safety Phrases ]:
26-36/37/39-45

[ RIDADR ]:
UN 1544 6.1/PG 2

[ WGK Germany ]:
3

[ RTECS ]:
PB9185700

[ HS Code ]:
2933990090

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

An efficient total synthesis of (-)-huperzine A.

Org. Lett. 14(17) , 4446-9, (2012)

The total synthesis of Lycopodium alkaloid (-)-huperzine A has been accomplished in 10 steps with 17% overall yield from commercially abundant (R)-pulegone. The synthetic route features an efficient s...

Induction of human CYP3A4 by huperzine A, ligustrazine and oridonin through pregnane X receptor-mediated pathways.

Pharmazie 69(7) , 532-6, (2014)

The pregnane X receptor (PXR) is a key regulator of CYP3A4, which is involved in catalyzing the metabolic conversion of a number of endogenous substrates. In this study, we screened 22 compounds isola...

Simultaneously preparative purification of Huperzine A and Huperzine B from Huperzia serrata by macroporous resin and preparative high performance liquid chromatography.

J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 904 , 65-72, (2012)

Huperzine A (HupA) and Huperzine B (HupB) are natural alkaloids existed in Lycopodium plants. They both have potential clinical application for treating Alzheimer's Disease (AD). For the purpose of be...

Related Compounds

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