Huperzine A

Huperzine A
Clinical data
Other namesHupA
Routes of
administration		Oral
ATC code
Pharmacokinetic data
Elimination half-life10-14h[1]
Identifiers
  • (1R,9R,13E)-1-Amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.02,7]trideca-2(7),3,10-trien-5-one
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.132.430 Edit this at Wikidata
Chemical and physical data
FormulaC15H18N2O
Molar mass242.322 g·mol−1
3D model (JSmol)
Melting point217 to 219 °C (423 to 426 °F)
  • C/C=C/1\[C@@H]2CC3=C([C@]1(CC(=C2)C)N)C=CC(=O)N3
  • InChI=1S/C15H18N2O/c1-3-11-10-6-9(2)8-15(11,16)12-4-5-14(18)17-13(12)7-10/h3-6,10H,7-8,16H2,1-2H3,(H,17,18)/b11-3+/t10-,15+/m0/s1 checkY
  • Key:ZRJBHWIHUMBLCN-YQEJDHNASA-N checkY
 ☒NcheckY (what is this?)  (verify)

Huperzine A is a naturally-occurring sesquiterpene alkaloid compound found in the firmoss Huperzia serrata[2] and in varying quantities in other food Huperzia species, including H. elmeri, H. carinat, and H. aqualupian.[3] Huperzine A has been investigated as a treatment for neurological conditions such as Alzheimer's disease, but a 2013 meta-analysis of those studies concluded that they were of poor methodological quality and the findings should be interpreted with caution.[4][5] Huperzine A inhibits the breakdown of the neurotransmitter acetylcholine (ACh) by the enzyme acetylcholinesterase. It is also an antagonist of the NMDA-receptor. It is commonly available over the counter as a nutritional supplement and marketed as a memory and concentration enhancer.

Huperzine A has also been noted to help induce lucid dreaming.[6]

  1. ^ Li YX, Zhang RQ, Li CR, Jiang XH (2007). "Pharmacokinetics of huperzine A following oral administration to human volunteers". European Journal of Drug Metabolism and Pharmacokinetics. 32 (4): 183–187. doi:10.1007/BF03191002. PMID 18348466. S2CID 2702029.
  2. ^ Cite error: The named reference Zangara2003 was invoked but never defined (see the help page).
  3. ^ Lim WH, Goodger JQ, Field AR, Holtum JA, Woodrow IE (September 2010). "Huperzine alkaloids from Australasian and southeast Asian Huperzia". Pharmaceutical Biology. 48 (9): 1073–1078. doi:10.3109/13880209.2010.485619. PMID 20731560.
  4. ^ Yang G, Wang Y, Tian J, Liu JP (2013). "Huperzine A for Alzheimer's disease: a systematic review and meta-analysis of randomized clinical trials". PLOS ONE. 8 (9): e74916. Bibcode:2013PLoSO...874916Y. doi:10.1371/journal.pone.0074916. PMC 3781107. PMID 24086396.
  5. ^ Cite error: The named reference cochranemeta was invoked but never defined (see the help page).
  6. ^ "Lucid Dreaming: A Beginner's Guide". The Four Hour Work Week. Retrieved 29 December 2016.