Huperzine A

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Huperzine A
Huperzine A
Huperzine A 3d
Identifiers
CAS number 102518-79-6 N
ChemSpider 16736021 YesY
UNII 0111871I23 N
DrugBank DB01928
ChEBI CHEBI:78330 N
ChEMBL CHEMBL395280 YesY
Jmol-3D images Image 1
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 (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

Huperzine A is a naturally occurring sesquiterpene alkaloid compound found in the firmoss Huperzia serrata[1] and in varying quantities in other Huperzia species, including H. elmeri, H. carinat, and H. aqualupian.[2]

Huperzine A has been found, through multiple studies, to be effective as a medicine for helping people with neurological conditions such as Alzheimer's disease, but the meta-analysis of those studies concluded that they were poor quality and the findings should be interpreted with caution.[3]

Pharmacological effects[edit]

Huperzine A is extracted from Huperzia serrata.[1] It is an acetylcholinesterase inhibitor[4][5] and NMDA receptor antagonist.[6] The structure of the complex of huperzine A with acetylcholinesterase has been determined by X-ray crystallography (PDB code: 1VOT; see the 3D structure).[7]

For some years, Huperzine A has been investigated as a possible treatment for diseases characterized by neurodegeneration – particularly Alzheimer's disease.[1][8] A 2013 systematic review and meta-analysis found "Huperzine A appears to have beneficial effects on improvement of cognitive function, daily living activity, and global clinical assessment in participants with Alzheimer’s disease. However, the findings should be interpreted with caution due to the poor methodological quality of the included trials."[9]

Huperzine A is also marketed as a dietary supplement with claims made for its ability to improve memory and mental function.[10]

Synthesis[edit]

Two scalable and efficient total syntheses of huperzine A have been reported.[11][12]

See also[edit]

References[edit]

  1. ^ a b c 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. 
  2. ^ 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. 
  3. ^ Yang, Guoyan. "Huperzine A for Alzheimer’s Disease: A Systematic Review and Meta-Analysis of Randomized Clinical Trials". Retrieved 22 October 2014. "Huperzine A appears to have beneficial effects on improvement of cognitive function, daily living activity, and global clinical assessment in participants with Alzheimer’s disease. However, the findings should be interpreted with caution due to the poor methodological quality of the included trials." 
  4. ^ 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. 
  5. ^ 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. 
  6. ^ 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. 
  7. ^ 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. 
  8. ^ 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. 
  9. ^ 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. 
  10. ^ Talbott, SM (2012). Huperzine A (HupA). A Guide to Understanding Dietary Supplements (Routledge). pp. 304–. ISBN 978-1-136-80570-7. 
  11. ^ Tun MK, 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. 
  12. ^ 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.