Huperzine A

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Huperzine A
Huperzine A
Huperzine A 3d
Identifiers
CAS number 102518-79-6 N
ChemSpider 16736021 YesY
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 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.[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] As of 2013 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.[3]

Huperzine A is also marketed as a dietary supplement with claims made for its ability to improve memory and mental function.[9]

Synthesis[edit]

Two scalable and efficient total syntheses of huperzine A have been reported.[10][11]

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. ^ a b 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. 
  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. ^ Talbott, SM (2012). "Huperzine A (HupA)". A Guide to Understanding Dietary Supplements (Routledge). pp. 304–. ISBN 978-1-136-80570-7. 
  10. ^ 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. 
  11. ^ 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.