Huperzine A

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Huperzine A
Huperzine A2DACS.svg
HuperzineA3d.png
Systematic (IUPAC) name
(1R,9S,13E)-1-Amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.02,7]trideca-2(7),3,10-trien-5-one
Clinical data
Routes of
administration		 Oral
Pharmacokinetic data
Biological half-life 10-14h[1]
Identifiers
CAS Number 102518-79-6 N
ATC code N06
DrugBank DB01928 YesY
ChemSpider 16736021 YesY
UNII 0111871I23 N
ChEBI CHEBI:78330 N
ChEMBL CHEMBL395280 YesY
Synonyms HupA
Chemical data
Formula C15H18N2O
Molecular mass 242.32 g/mol
  • C\C2=C\[C@H]\3CC=1NC(=O)\C=C/C=1[C@@](N)(C2)C/3=C\C
  • 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 YesY
  • Key:ZRJBHWIHUMBLCN-YQEJDHNASA-N YesY
Physical data
Melting point 217 to 219 °C (423 to 426 °F)
 NYesY (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 Huperzia species, including H. elmeri, H. carinat, and H. aqualupian.[3]

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.[4][5]

Pharmacological effects

Huperzine A is extracted from Huperzia serrata.[2] It is a reversible acetylcholinesterase inhibitor[6] [7][8] and NMDA receptor antagonist[9] that crosses the blood-brain barrier.[10] The structure of the complex of huperzine A with acetylcholinesterase has been determined by X-ray crystallography (PDB code: 1VOT; see the 3D structure).[11]

For some years, huperzine A has been investigated as a possible treatment for diseases characterized by neurodegeneration – particularly Alzheimer's disease.[2][12] A 2013 meta-analysis found that huperzine A may be efficacious in improving cognitive function, global clinical status, and activities of daily living for individuals with Alzheimer’s disease. However, due to the poor size and quality of the clinical trials reviewed, huperzine A should not be recommended as a treatment for Alzheimer’s disease until further high quality studies confirm its beneficial effects.[4]

Huperzine A is also marketed as a dietary supplement with claims made for its ability to improve memory and mental function.[13] Huperzine A may also have a possible role in the treatment of myasthenia gravis.[14]

Adverse effects

Huperzine A may present with mild cholinergic side effects such as nausea, vomiting and diarrhea.[5]

The use of huperzine A during pregnancy and lactation is not recommended due to the lack of sufficient safety data.[15]

Drug interactions

Huperzine A it may have additive effects if taken with drugs causing bradycardia, such as beta-blockers.[14] which may decrease heart rate

Theoretically, there may be possible additive cholinergic effects if huperzine A is taken with other acetylcholinesterase inhibitors or cholinergic agents.[16]

Synthesis

Two scalable and efficient total syntheses of huperzine A have been reported.[17][18]

See also

References

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  2. ↑ 2.0 2.1 2.2 Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ 4.0 4.1 Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ 5.0 5.1 Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  10. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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  13. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  14. ↑ 14.0 14.1 Lua error in package.lua at line 80: module 'strict' not found.
  15. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  16. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  17. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  18. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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