(-)-Huperzine A

(-)-Huperzine A (Huperzine A) is an alkaloid isolated from a Chinese club moss, with neuroprotective activity. (-)-Huperzine A is a potent, highly specific, reversible and blood-brain barrier penetrant inhibitor of acetylcholinesterase (AChE), with an IC50 of 82 nM. (-)-Huperzine A also is non-competitive antagonist of N-methyl-D-aspartate glutamate (NMDA) receptor. (-)-Huperzine A is developed for the research of neurodegenerative diseases, including Alzheimer’s disease.

Product information

CAS Number: 102518-79-6

Molecular Weight: 242.32

Formula: C15H18N2O

Synonym:

(-)-Selagine

Huperzine A

Selagine

Chemical Name: (1R, 9R, 13Z)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.0, ]trideca-2(7), 3, 10-trien-5-one

Smiles: CC1C[C@@]2(N)/C(=C\C)/[C@H](CC3NC(=O)C=CC2=3)C=1

InChiKey: ZRJBHWIHUMBLCN-SEQYCRGISA-N

InChi: InChI=1S/C15H18N2O/c1-3-11-10-6-9(2)8-15(11,16)12-4-5-14(18)17-13(12)7-10/h3-6,10H,7-8,16H2,1-2H3,(H,17,18)/b11-3-/t10-,15+/m0/s1

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: DMSO: 0.66 mg/mL(2.72 mM).

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥360 days if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

(-)-Huperzine A is a novel alkaloid isolated from the Chinese herb Huperzia serrata. (-)-Huperzine A preferentially inhibits tetrameric AChE (G4 form). (-)-Huperzine A is more potent than tacrine, physostigmine, galanthamine, and rivastigmine with respect to inhibition of AChE activity, whereas HupA is the least potent BuChE inhibitor among the inhibitors. (-)-Huperzine A possesses the ability to protect cells against hydrogen peroxide, β-amyloid protein, glutamate, ischemia and staurosporine-induced cytotoxicity and apoptosis. These protective effects are related to its ability to attenuate oxidative stress, regulate the expression of apoptotic proteins Bcl-2, Bax, P53, and caspase-3, protect mitochondria, upregulate nerve growth factor and its receptors, and interfere with amyloid precursor protein metabolism.

In Vivo:

(-)-Huperzine A can ameliorate the learning and memory deficiency in animal models and AD patients. Its potentially beneficial actions include modification of β-amyloid peptide processing, reduction of oxidative stress, neuronal protection against apoptosis, and regulation of the expression and secretion of nerve growth factor (NGF) and NGF signaling. (-)-Huperzine A significantly inhibits AChE activity in the cortex, hippocampus, striatum, medial septum, medulla oblongata, cerebellum, and hypothalamus of rats that are killed 30 min following the administration of (-)-Huperzine A at several dose levels compared with the saline control.

References:

1. Wang R, et al. Acta Pharmacol Sin, 2006, 27(1), 1-26.
2. Zhang HY, et al. Trends Pharmacol Sci, 2006, 27(12), 619-625.
3. Zhao Q, et al. Eur J Pharmacol, 2002, 455(2-3), 101-107.

Products are for research use only. Not for human use.