Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C15H18N2O |
Molecular Weight | 242.3162 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C\C=C1/[C@@H]2CC3=C(C=CC(=O)N3)[C@@]1(N)CC(C)=C2
InChI
InChIKey=ZRJBHWIHUMBLCN-YQEJDHNASA-N
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
Molecular Formula | C15H18N2O |
Molecular Weight | 242.3162 |
Charge | 0 |
Count |
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Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 1 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://doi.org/10.1016/j.jalz.2009.05.218 | https://adisinsight.springer.com/drugs/800016260http://www.webmd.com/vitamins-supplements/ingredientmono-764-huperzine%20a.aspxCurator's Comment: description was created based on several sources, including:
https://www.braintropic.com/nootropics/huperzine-a/ | https://www.drugs.com/npc/huperzine-a.html | http://medind.nic.in/daa/t11/i1/daat11i1p177.pdf
Sources: https://doi.org/10.1016/j.jalz.2009.05.218 | https://adisinsight.springer.com/drugs/800016260http://www.webmd.com/vitamins-supplements/ingredientmono-764-huperzine%20a.aspx
Curator's Comment: description was created based on several sources, including:
https://www.braintropic.com/nootropics/huperzine-a/ | https://www.drugs.com/npc/huperzine-a.html | http://medind.nic.in/daa/t11/i1/daat11i1p177.pdf
Huperzine A is a plant alkaloid derived from Club moss plant, Huperzine serrata, which is a member or the Lycopodium species. Huperzine-A is in phase III clinical trial in the USA (Alzheimer disease) and is available as a dietary supplement. It selectively and reversibly inhibits acetylcholinesterase. Huperzine A is also a NMDA receptor antagonist, which protects the brain against glutamate induced damage, and it increases nerve growth factor levels. Huperzine A is used for Alzheimer's disease, memory and learning enhancement, and age-related memory impairment. It is also used for treating a muscle disease called myasthenia gravis, for increasing alertness and energy, and for protecting against agents that damage the nerves such as nerve gases. It can cause some side effects including nausea, diarrhea, vomiting, sweating, blurred vision, slurred speech, restlessness, loss of appetite, contraction and twitching of muscle fibers, cramping, increased saliva and urine, inability to control urination, high blood pressure, and slowed heart rate. Various medications used for glaucoma, Alzheimer's disease, and other conditions (Cholinergic drugs) interacts with Huperzine A.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL220 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10375798 |
64.7 nM [IC50] | ||
Target ID: CHEMBL1907608 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10437121 |
0.5 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Palliative | Unknown Approved UseUnknown |
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Primary | Huperzine A Approved UseHuperzine A can be used as a memory enhancer. It can also be taken regularly to help protect against age-related declines in memory. |
PubMed
Title | Date | PubMed |
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Comparative effects of huperzine A, donepezil and rivastigmine on cortical acetylcholine level and acetylcholinesterase activity in rats. | 2004 May 6 |
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Effective countermeasure against poisoning by organophosphorus insecticides and nerve agents. | 2006 Aug 29 |
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The combination of huperzine A and imidazenil is an effective strategy to prevent diisopropyl fluorophosphate toxicity in mice. | 2008 Sep 16 |
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The role of cholinergic anti-inflammatory pathway in acetic acid-induced colonic inflammation in the rat. | 2013 Sep 5 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://doi.org/10.1016/j.jalz.2009.05.218
Patients in the mimopezil arm received 1 mg mimopezil daily orally during the 1-month titration period, 9 mg mimopezil as s.c. implants in the 1-month maintenance I period, and 12 mg mimopezil as s.c. implants in the 4-month maintenance II period.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7898122
The synthetic racemic mixture (+/-)-huperzine-A was 3 times less potent than (-)-huperzine-A in vitro (IC50s of 3 x 10(-7) M and 10(-7) M, respectively) because the former consisted of a racemic mixture of the compound in which the (+)-huperzine component was considerably less potent (IC50 = 7 x 10(-6) M).
Substance Class |
Chemical
Created
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Record UNII |
0111871I23
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
744420
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DSLD |
708 (Number of products:164)
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NCI_THESAURUS |
C66880
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DSLD |
3336 (Number of products:266)
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FDA ORPHAN DRUG |
559916
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FDA ORPHAN DRUG |
885322
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178022
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HUPERZINE A
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DB04864
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SUB127430
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102518-79-6
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100000153436
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m6064
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854026
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0111871I23
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SUB33678
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C97271
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C050426
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78330
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Related Record | Type | Details | ||
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SOLVATE->ANHYDROUS |
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SALT/SOLVATE -> PARENT |
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TARGET -> INHIBITOR |
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PRODRUG -> METABOLITE ACTIVE |
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ACTIVE MOIETY |
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