Huperzine A
| 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)=C\C |
| 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 botanical 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.
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.
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 efficiency of huperzine A in the treatment of Alzheimer's disease in a randomized controlled trial of its effect on cognitive function. Recently, it has been investigated for it's effectiveness against epilepsy in an initial 20-person clinical study by Harvard University neuroscientists examining its worth and side effects in those who are not satisfactorily treated by existing pharmaceuticals.
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.
- PDR entry for Huperzine A