Huperzine A
General
Systematic name	1-Amino-13-ethylidene-11-methyl- 6-aza-tricyclo[7.3.1.02,7]trideca- 2(7),3,10-trien-5-one
Other names	HupA
Molecular formula	C15H18N2O
SMILES	CC3=CC1/C(C(C3)(N)C (C=CC2=O)=C(N2)C1)=CC
Molar mass	242.32 g/mol
Appearance	?
CAS number	[102518-79-6]
Properties
Density and phase	? g/cm3, ?
Solubility in water	? g/100 ml (? °C)
Melting point	217-219 °C (? K)
Boiling point	? °C (? K)
Basicity (pKb)	?
Chiral rotation [α]D	-147° (c = 0.36, MeOH)
Hazards
MSDS	External MSDS
Main hazards	?
NFPA 704
Flash point	? °C
R/S statement	R: ? S: ?
RTECS number	?
Related compounds
Related compounds	?
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Huperzine A, is a naturally occurring sesquiterpene alkaloid found in the extracts of the firmoss Huperzia serrata. The extract has been used in China for centuries for the treatment of swelling, fever and blood disorders. Recently in clinical trials in China, it has demonstrated neuroprotective effects. It is currently being investigated as a possible treatment for diseases characterized by neurodegeneration – particularly Alzheimer’s disease. IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... Density (symbol: ρ - Greek: rho) is a measure of mass per volume. ... In the physical sciences, a phase is a set of states of a macroscopic physical system that have relatively uniform chemical composition and physical properties (i. ... It has been suggested that this article or section be merged with Solution. ... This article describes water from a scientific and technical perspective. ... The melting point of a solid is the temperature at which it changes state from solid to liquid. ... The boiling point of a substance is the temperature at which it can change its state from a liquid to a gas throughout the bulk of the liquid at a given pressure. ... In chemistry and biochemistry, the acid dissociation constant, the acidity constant, or the acid-ionization constant (Ka) is a specific type of equilibrium constant that indicates the extent of dissociation of hydrogen ions from an acid. ... The specific rotation of a chemical compound [α]D is defined as the observed angle of optical rotation α when light of 589 nanometer wavelength (the sodium D line) is passed through a sample with a path length of 0. ... Methanol, also known as methyl alcohol or wood alcohol, is a chemical compound with chemical formula CH3OH. It is the simplest alcohol, and is a light, volatile, colourless, flammable, poisonous liquid with a distinctive odor that is somewhat sweeter than ethanol (ethyl alcohol). ... A material safety data sheet or MSDS is a form containing data regarding the properties of a particular substance. ... The examples and perspective in this article or section may not represent a worldwide view. ... NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. ... The flash point of a flammable liquid is the lowest temperature at which it can form an ignitable mixture with air. ... Risk and Safety Statements, also known as R/S statements, R/S numbers, R/S phrases, and R/S sentences, is a system of hazard codes and phrases for labeling dangerous chemicals and compounds. ... R-phrases are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous substances and preparations. ... S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. ... RTECS, also known as Registry of Toxic Effects of Chemical Substances, is a database of toxicity information compiled from the open scientific literature that is available for charge. ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... Diagram of Ephedrine An alkaloid is a nitrogenous organic molecule that has a pharmacological effect on humans and animals. ... Species - Appalachian firmoss - Shining firmoss - Rock firmoss - Northern firmoss Firmosses are plants of the Lycophyte genus Huperzia. ... The term neuroprotection means mechanisms within the nervous system which protect neurons from apoptosis or degeneration, for example following a braininjury or as a result of chronic neurodegenerative diseases. ... Alzheimers disease (AD) or primary dementia of Alzheimers type is an incurable, degenerative neuropsychiatric disease which results in a pervasive loss of first mental, then physical functioning due to the deterioration of brain tissue. ...

Huperzine A has attracted the attention of Western medical science. It has been found to be an inhibitor of the enzyme acetylcholinesterase. This is the same mechanism of action of pharmaceutical drugs such as galantamine and donepezil used to treat Alzheimer's disease. An enzyme inhibitor is a molecule that binds to an enzyme and decreases its rate of reaction. ... In biochemistry, cholinesterase is a term which refers to one of the two enzymes (EC 3. ... Wikipedia does not yet have an article with this exact name. ... Galantamine (trade name Razadyne®) is a medication used in the treatment of Alzheimers disease. ... Donepezil, marketed under the trade name Aricept® (Eisai), is a centrally acting reversible acetyl cholinesterase inhibitor. ...

Clinical trials in China have shown that huperzine A is comparably effective to the drugs currently on the market, and may even be a bit safer in terms of side effects. Currently, the National Institute on Aging is conducting 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. The National Institute on Aging is a division of the National Institutes of Health, located in Bethesda,_Maryland. ...

References

• Zangara, A. The psychopharmacology of huperzine A: an alkaloid with cognitive enhancing and neuroprotective properties of interest in the treatment of Alzheimer's disease. Pharmacol Biochem Behav. 2003 Jun;75(3):675-86.
• Bai, D. L.; Tang, X. C.; He, X. C. Huperzine A, a potential therapeutic agent for treatment of Alzheimer's disease. Current Medicinal Chemistry , 2000, vol. 7, iss. 3, p. 355-374.
• Tang, X. C.; He, X. C.; Bai, D. L. Huperzine A: a novel acetylcholinesterase inhibitor. Drugs of the Future, 1999, vol. 24, iss 6, p. 647-663.
• Kozikowski, Alan P.; Tueckmantel, Werner. Chemistry, Pharmacology, and Clinical Efficacy of the Chinese Nootropic Agent Huperzine A. Accounts of Chemical Research, 1999, vol 32, iss 8, p. 641-650.

External links

• Link page to external chemical sources.