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Huperzine A
Identifiers
CAS number 102518-79-6
SMILES
Properties
Molecular formula C15H18N2O
Molar mass 242.32 g/mol
Melting point

217-219 °C

Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Huperzine A, is a naturally occurring sesquiterpene alkaloid compound found in the plant firmoss Huperzia serrata.[1]

Huperzine A is an Acetylcholinesterase inhibitor similar to other compounds donepezil, rivastigmine, and galantamine.

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 has shown it to be effective in the treatment of Alzheimer's disease,[2] and has been shown to enhance memory in healthy young students in one study. [3]

Pharmacological effects

Acetylcholinesterase inhibition[4] and NMDA receptor antagonism.[5]

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 – particularly Alzheimer’s disease.[6][7] It has been found to be an inhibitor of the enzyme acetylcholinesterase.[8] The structure of the complex of huperzine A with acetylcholinesterase has been solved 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[citation needed] which protects the brain against glutamate induced damage, and it increases nerve growth factor levels.[citation needed]

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.[citation needed] 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 its 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.[citation needed]

Possible side effects may 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.[9] Most adverse events were cholinergic in nature and no serious adverse events occurred. Huperzine A is a well-tolerated drug.[10]

See also

References

  1. ^ Kozikowski, Alan P.; Tueckmantel, Werner (1999). "Chemistry, Pharmacology, and Clinical Efficacy of the Chinese Nootropic Agent Huperzine A". Accounts of Chemical Research 32 (8): 641–650. doi:10.1021/ar9800892. 
  2. ^ J Neural Transm. 2009 Apr;116(4):457-65. Epub 2009 Feb 17
  3. ^ Zhongguo Yao Li Xue Bao. 1999 Jul;20(7):601-3. Huperzine-A capsules enhance memory and learning performance in 34 pairs of matched adolescent students.
  4. ^ Coleman; Ratcliffe, R.; Oguntayo, S.; Shi, X.; Doctor, B.; Gordon, R.; Nambiar, M. (2008). "+-Huperzine a treatment protects against N-methyl-D-aspartate-induced seizure/status epilepticus in rats". Chemico-biological interactions 175 (1-3): 387–395. doi:10.1016/j.cbi.2008.05.023. PMID 18588864.  edit
  5. ^ Wang; Wang, H.; Wei, Z.; Song, Y.; Zhang, L.; Chen, H. (2009). "Efficacy and safety of natural acetylcholinesterase inhibitor huperzine a in the treatment of Alzheimer's disease: an updated meta-analysis". Journal of neural transmission (Vienna, Austria : 1996) 116 (4): 457–465. doi:10.1007/s00702-009-0189-x. PMID 19221692.  edit
  6. ^ Zangara, A (2003). "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. 75 (3): 675–86. doi:10.1016/S0091-3057(03)00111-4. 
  7. ^ Bai, D. L.; Tang, X. C.; He, X. C. (2000). "Huperzine A, a potential therapeutic agent for treatment of Alzheimer's disease". Current Medicinal Chemistry 7 (3): 355–374. 
  8. ^ Tang, X. C.; He, X. C.; Bai, D. L. (1999). "Huperzine A: a novel acetylcholinesterase inhibitor". Drugs of the Future 24 (6): 647–663. doi:10.1358/dof.1999.024.06.545143. 
  9. ^ PDR entry for Huperzine A
  10. ^ B.S. Wang et al., Efficacy and safety of natural acetylcholinesterase inhibitor huperzine A in the treatment of Alzheimer's disease: an updated meta-analysis, J Neural Transm vol. 116, no. 4(Apr 2009), pp. 457-652009.
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