Huperzine A

Names

[ CAS No. ]:
120786-18-7

[ Name ]:
Huperzine A

[Synonym ]:
(+-)-HUPERZINE A
5,9-METHANOCYCLOOCTA[B]PYRIDIN-2(1H)-ONE,5-AMINO-11-ETHYLIDENE-5,6,9,10-TETRAHYDRO-7-METHYL-, (11E)-
HUPERZINE A (+/-)-
MFCD00171439
5,9-Methanocycloocta[b]pyridin-2(1H)-one, 5-amino-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-, (11E)-
(±)-Huperzine A
(+/-)-HUPERZINE A
(+/-)-Huperazine A
Huperzine A
(13E)-1-Amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0]trideca-2(7),3,10-trien-5-one
(11E)-5-amino-11-ethylidene-7-methyl-5,6,9,10-tetrahydro-5,9-methanocycloocta[b]pyridin-2(1H)-one

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]:
1.2±0.1 g/cm3

[ Boiling Point ]:
505.0±50.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₅H₁₈N₂O

[ Molecular Weight ]:
242.316

[ Flash Point ]:
259.2±30.1 °C

[ Exact Mass ]:
242.141907

[ PSA ]:
58.88000

[ LogP ]:
0.71

[ Vapour Pressure ]:
0.0±1.3 mmHg at 25°C

[ Index of Refraction ]:
1.626

[ Storage condition ]:
2-8°C

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301 + H311 + H331-H315-H319-H335

[ Precautionary Statements ]:
P261-P280-P301 + P310-P305 + P351 + P338-P311

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges

[ Hazard Codes ]:
T

[ Risk Phrases ]:
23/24/25-36/37/38

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

[ RIDADR ]:
UN 1544 6.1/PG 2

[ WGK Germany ]:
3

[ RTECS ]:
PB9185700

Articles

Effect of huperzine A, a new cholinesterase inhibitor, on the central cholinergic system of the rat.

J. Neurosci. Res. 24 , 276, (1989)

The present study represents the first comprehensive investigation of the effect of huperzine A (HUP-A), a new cholinesterase inhibitor (ChEI) isolated from a Lycopodium species, upon acetylcholineste...

Effect of triterpenoid saponins from Bacopa monniera on scopolamine-induced memory impairment in mice.

Planta Med. 75 , 568-74, (2009)

Three new saponins, bacopasides IX-XI (1- 3), together with their known analogues bacopaside I (4), bacopaside II (5), bacopasaponsin C (6), and bacopasaponsin D (7), were isolated from the whole plan...