|Jmol-3D images||Image 1|
|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 (77 °F), 100 kPa)|
|(what is: / ?)|
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 has been investigated for its potential as a medicine for helping people with neurological conditions such as Alzheimer's disease, but there is insufficient medical evidence for it to be recommended.
Huperzine A is extracted from Huperzia serrata. It is an acetylcholinesterase inhibitor and NMDA receptor antagonist. The structure of the complex of huperzine A with acetylcholinesterase has been determined by X-ray crystallography (PDB code: 1VOT; see the 3D structure).
For some years, Huperzine A has been investigated as a possible treatment for diseases characterized by neurodegeneration – particularly Alzheimer's disease. As of 2013[update] although some research suggests it may be helpful, the evidence overall is not convincing enough for it to be recommended for use as a medicine, and little is known of its safety.
Huperzine A is also marketed as a dietary supplement with claims made for its ability to improve memory and mental function.
- 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". Pharmacology, biochemistry, and behavior 75 (3): 675–86. doi:10.1016/S0091-3057(03)00111-4. PMID 12895686.
- Lim W, Goodger J, Field A, Holtum J, Woodrow I (2010). "Huperzine alkaloids from Australasian and southeast Asian Huperzia". Pharmaceutical biology 48 (9): 1073–8. doi:10.3109/13880209.2010.485619. PMID 20731560.
- Yang G, Wang Y, Tian J, Liu J (2013). "Huperzine a for Alzheimer's Disease: A Systematic Review and Meta-Analysis of Randomized Clinical Trials". PLoS ONE 8 (9): e74916. doi:10.1371/journal.pone.0074916. PMC 3781107. PMID 24086396.
- Wang B, 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): 457–65. doi:10.1007/s00702-009-0189-x. PMID 19221692.
- Tang X, He X, Bai D (1999). "Huperzine A: A novel acetylcholinesterase inhibitor". Drugs of the Future 24 (6): 647. doi:10.1358/dof.1999.024.06.545143.
- Coleman B, 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): 387–95. doi:10.1016/j.cbi.2008.05.023. PMID 18588864.
- Raves M, Harel M, Pang Y, Silman I, Kozikowski A, Sussman J (1997). "Structure of acetylcholinesterase complexed with the nootropic alkaloid, (-)-huperzine A". Nature structural biology 4 (1): 57–63. doi:10.1038/nsb0197-57. PMID 8989325.
- Bai D, Tang X, He X (2000). "Huperzine A, a potential therapeutic agent for treatment of Alzheimer's disease". Current medicinal chemistry 7 (3): 355–74. doi:10.2174/0929867003375281. PMID 10637369.
- Talbott, SM (2012). "Huperzine A (HupA)". A Guide to Understanding Dietary Supplements (Routledge). pp. 304–. ISBN 978-1-136-80570-7.
- Tun MKM, Wüstmann D, Herzon SB (2011). "A robust and scalable synthesis of the potent neuroprotective agent (−)-huperzine A". Chemical Science 2 (11): 2251. doi:10.1039/C1SC00455G.
- Tudhope SR, Bellamy JA, Ball A, Rajasekar D, Azadi-Ardakani M, Meera HS, Gnanadeepam JM, Saiganesh R, Gibson F, He L, Behrens CH, Underiner G, Marfurt J, Favre N (2012). "Development of a Large-Scale Synthetic Route to Manufacture (−)-Huperzine A". Organic Process Research & Development 16 (4): 635. doi:10.1021/op200360b.