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Application: An inhibitor of AChE and antagonist of NMDA receptors
CAS Number: 102518-79-6
Molecular Weight: 242.32
Molecular Formula: C15H18N2O
(-)-Huperzine A is a natural product that acts as an NMDA receptor antagonist and reversible inhibitor of AChE (acetylcholinesterase),
the enzyme primarily responsible for degradation of the neurotransmitter acetylcholine and termination of the acetylcholine synaptic signal.
(-)-Huperzine A is the more potent stereoisomer of racemic (¡À)-Huperzine A preparations, an approximately 38-fold more potent inhibitor of AChE than (+)-Huperzine A.
Both the (-) and (+) stereoisomers also demonstrate NMDA receptor antagonism with similar affinity.
Pretreatment of cerebral neuronal cells with (-)-Huperzine A confers protection against glutamate-mediated Ca2+ influx and excitotoxicity,
moderated by blockade of NMDA-associated ion channel activity.
Disruption of spatial memory induced by scopolamine and muscimol was reversed by introduction of (-)-Huperzine A.
Excitotoxicity resulting from organophosphorous nerve agent-induced accumulation of acetylcholine, also mediated through NMDA receptor stimulation,
is diminished by exposure to the enantiomer (+)-Huperzine A and preparations of (¡À)-Huperzine A are suggested for use in nerve agent protection.
(-)-Huperzine A is demonstrated to suppress cerebral hypoperfusion-related inflammation through its indirect effects upon the nicotinic acetylcholine receptor.
Physical State: Solid
Derived from: Lycopodium sp.
Solubility: Soluble in methanol, and DMSO. Insoluble in water.
Storage: Store at -20¡ã C
Melting Point: 214-215 ¡ãC
Boiling Point: 505.01 ¡ãC at 760 mmHg
Density: 1.20 g/cm3
Refractive Index: n20D 1.63
Safety and Reference Information
Transport: UN 1544, Class 6.1, Packing group II
WGK Germany: 3
PubChem CID: 907504
Merck Index: 14: 4755
MDL Number: MFCD01714949
C/C=C1/[[email protected]@H]2CC3=C([[email protected]]1(CC(=C2)C)N)C=CC(=O)N3
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
Huperzine AFrom Wikipedia, the free encyclopedia
Jump to: navigation, search Huperzine A
CAS number 102518-79-6 N
ChemSpider 16736021 Y
ChEMBL CHEMBL395280 Y
Jmol-3D images Image 1
[show]CC2=C[[email protected]]3CC=1NC(=O)C=C/C=1[[email protected]@](N)(C2)C/3=CC
Key: ZRJBHWIHUMBLCN-YQEJDHNASA-N Y
Molecular formula C15H18N2O
Molar mass 242.32 g/mol
Melting point 217¨C219 ¡ãC
Except where noted otherwise, data are given for materials in their standard state (at 25 ¡ãC, 100 kPa)
Huperzine A is a naturally occurring sesquiterpene alkaloid compound found in the firmoss Huperzia serrata. and in varying quantities in other Huperzia species,
including H. elmeri, H. carinat, and H. aqualupian.
Huperzine A is also an acetylcholinesterase inhibitor, which has a mechanism of action similar to donepezil,
rivastigmine, and galantamine. A pro-drug form of huperzine A (ZT-1) is under development as a treatment for Alzheimer¡¯s disease.
In the US, huperzine A is sold as a dietary supplement for memory support.
The botanical has been used in China for centuries for the treatment of swelling, fever and blood disorders.
Clinical trials in China have shown it to be effective in improving cognitive performance in patients with Alzheimer¡¯s disease and
enhancing memory in adolescents complaining of memory inadequacy.
Pharmacological effectsHuperzine A is an acetylcholinesterase inhibititor and NMDA receptor antagonist.
Huperzine A has also attracted the attention of US medical science.
It is currently being investigated as a possible treatment for diseases characterized by neurodegeneration ¨C particularly Alzheimer¡¯s disease.
It has been found to be an inhibitor of the enzyme acetylcholinesterase.
The structure of the complex of huperzine A with acetylcholinesterase has been determined by X-ray crystallography (PDB code: 1VOT; see the 3D structure).
This is the same mechanism of action of pharmaceutical drugs such as galantamine and donepezil used to treat Alzheimer¡¯s disease.
Huperzine A is also a NMDA receptor antagonist which may either reduce or increase glutamate induced damage in brain and increase nerve growth factor levels in rats.
Clinical trials in China have shown that huperzine A is comparably effective to similar drugs on the market, and may even be safer in terms of side effects.
The National Institute on Aging has completed a Phase II clinical trial to evaluate the safety and efficacy of huperzine A in the treatment of
Alzheimer¡¯s disease in a randomized controlled trial of its effect on cognitive function.
In 2008, the National Institute on Aging conducted the first controlled trial outside of China evaluating the efficacy and toxicity of huperzine A
to improve cognitive function in patients with AD. In this multi-center, double-blind, placebo-controlled Phase II trial,
210 participants with mild to moderate AD received either 200 mcg of huperzine A, 400 mcg of huperzine A, or placebo twice daily for 16 weeks.
While no statistical difference in cognitive scores was noted in patients in the lower dose huperzine A group compared to placebo,
the higher dose (400 mcg) of huperzine A led to improved cognition and activities of daily living.
However, no significant changes were noted in any of the three groups in overall change in disease or in psychiatric ratings according to the AD Assessment Scale-Cognitive (ADAS-Cog) scale.
Huperzine A was safe and well tolerated in the study. (13)
The same year, a Cochrane Database review examined studies evaluating the efficacy and safety of huperzine A in the treatment of AD.
The review included six randomized, controlled trials involving 454 patients.
Huperzine A seemed to have beneficial effects on improvement of general cognitive function, global clinical status,
behavioral disturbance and function performance with no serious side effects for patients with AD.
Possible side effects include breathing problems, tightness in the throat or chest, chest pain, skin hives, rash, itchy or swollen skin,
upset stomach, diarrhea, vomiting, hyperactivity and insomnia.
Most adverse events were cholinergic in nature and no serious adverse events occurred. Huperzine A is a well-tolerated drug.
SynthesisTwo scalable and efficient total syntheses of huperzine A have been reported.
See alsoAcetylcholinesterase inhibitor and AChE inhibitors and substrates in Proteopedia