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MedKoo Cat#: 600142 | Name: Huperzine A
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Huperzine A is an acetylcholinesterase inhibitor and NMDA receptor antagonist. Huperzine A is extracted from Huperzia serrata. Huperzine A has been investigated as a possible treatment for diseases characterized by neurodegeneration – particularly Alzheimer's disease. 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. Huperzine A is also marketed as a dietary supplement with claims made for its ability to improve memory and mental function. (http://en.wikipedia.org/wiki/Huperzine_A).

Chemical Structure

Huperzine A
Huperzine A
CAS#102518-79-6

Theoretical Analysis

MedKoo Cat#: 600142

Name: Huperzine A

CAS#: 102518-79-6

Chemical Formula: C15H18N2O

Exact Mass: 242.1419

Molecular Weight: 242.32

Elemental Analysis: C, 74.35; H, 7.49; N, 11.56; O, 6.60

Price and Availability

Size Price Availability Quantity
100mg USD 350.00 2 Weeks
250mg USD 650.00 2 Weeks
500mg USD 1,050.00 2 Weeks
1g USD 1,850.00 2 Weeks
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Synonym
Huperzine A; Selagine; (-)-huperzine A; (-)-Selagine.
IUPAC/Chemical Name
(5S,9R,E)-5-amino-11-ethylidene-7-methyl-5,6,9,10-tetrahydro-5,9-methanocycloocta[b]pyridin-2(1H)-one.
InChi Key
ZRJBHWIHUMBLCN-HZRLMBICSA-N
InChi Code
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
SMILES Code
O=C(N1)C=CC2=C1C[C@H]3/C([C@@]2(N)CC(C)=C3)=C\C
Appearance
solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO.
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Huperzine A, is a naturally occurring sesquiterpene alkaloid found in the extracts of the firmoss Huperzia serrata. The botanical has been used in China for centuries for the treatment of swelling, fever and blood disorders. Recently in clinical trials in China, it has demonstrated neuroprotective effects. It is currently being investigated as a possible treatment for diseases characterized by neurodegeneration - particularly Alzheimer's disease.
Product Data
Product Data
Instruction
View handling instruction
Biological target:
(-)-Huperzine A is a potent, highly specific, reversible and blood-brain barrier penetrant inhibitor of acetylcholinesterase (AChE), with an IC50 of 82 nM. (-)-Huperzine A also is non-competitive antagonist of N-methyl-D-aspartate glutamate (NMDA) receptor.
In vitro activity:
These results revealed that FFA decreased the cell proliferation activity and viability, but huperzine A reversed the role of FFA in reducing the cell proliferative activity and viability. Reference: PeerJ. 2018 Jun 26;6:e5145. https://pubmed.ncbi.nlm.nih.gov/29967757/
In vivo activity:
However, treatment with HupA (Huperzine A) partially rescued GPx activity after TBI (Figure 4B). These data suggest that HupA alleviates oxidative stress and enhances anti-oxidant enzyme activity after TBI. Reference: Iran J Basic Med Sci. 2021 Oct;24(10):1455-1461. https://pubmed.ncbi.nlm.nih.gov/35096305/
Solvent mg/mL mM
Solubility
DMSO 60.0 247.60
Methanol 1.0 4.13
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 242.32 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Hu XN, Wang JF, Huang YQ, Wang Z, Dong FY, Ma HF, Bao ZJ. Huperzine A attenuates nonalcoholic fatty liver disease by regulating hepatocyte senescence and apoptosis: an in vitro study. PeerJ. 2018 Jun 26;6:e5145. doi: 10.7717/peerj.5145. PMID: 29967757; PMCID: PMC6025153. 2. Zhu N, Lin J, Wang K, Wei M, Chen Q, Wang Y. Huperzine A protects neural stem cells against Aβ-induced apoptosis in a neural stem cells and microglia co-culture system. Int J Clin Exp Pathol. 2015 Jun 1;8(6):6425-33. PMID: 26261518; PMCID: PMC4525852. 3. Mei Z, Hong Y, Yang H, Sheng Q, Situ B. Huperzine A protects against traumatic brain injury through anti-oxidative effects via the Nrf2-ARE pathway. Iran J Basic Med Sci. 2021 Oct;24(10):1455-1461. doi: 10.22038/IJBMS.2021.58169.12932. PMID: 35096305; PMCID: PMC8769513. 4. Yu P, Dong WP, Tang YB, Chen HZ, Cui YY, Bian XL. Huperzine A lowers intraocular pressure via the M3 mAChR and provides retinal neuroprotection via the M1 mAChR: a promising agent for the treatment of glaucoma. Ann Transl Med. 2021 Feb;9(4):332. doi: 10.21037/atm-20-8093. PMID: 33708959; PMCID: PMC7944337.
In vitro protocol:
1. Hu XN, Wang JF, Huang YQ, Wang Z, Dong FY, Ma HF, Bao ZJ. Huperzine A attenuates nonalcoholic fatty liver disease by regulating hepatocyte senescence and apoptosis: an in vitro study. PeerJ. 2018 Jun 26;6:e5145. doi: 10.7717/peerj.5145. PMID: 29967757; PMCID: PMC6025153. 2. Zhu N, Lin J, Wang K, Wei M, Chen Q, Wang Y. Huperzine A protects neural stem cells against Aβ-induced apoptosis in a neural stem cells and microglia co-culture system. Int J Clin Exp Pathol. 2015 Jun 1;8(6):6425-33. PMID: 26261518; PMCID: PMC4525852.
In vivo protocol:
1. Mei Z, Hong Y, Yang H, Sheng Q, Situ B. Huperzine A protects against traumatic brain injury through anti-oxidative effects via the Nrf2-ARE pathway. Iran J Basic Med Sci. 2021 Oct;24(10):1455-1461. doi: 10.22038/IJBMS.2021.58169.12932. PMID: 35096305; PMCID: PMC8769513. 2. Yu P, Dong WP, Tang YB, Chen HZ, Cui YY, Bian XL. Huperzine A lowers intraocular pressure via the M3 mAChR and provides retinal neuroprotection via the M1 mAChR: a promising agent for the treatment of glaucoma. Ann Transl Med. 2021 Feb;9(4):332. doi: 10.21037/atm-20-8093. PMID: 33708959; PMCID: PMC7944337.
1: Qian ZM, Ke Y. Huperzine A: Is it an Effective Disease-Modifying Drug for Alzheimer's Disease? Front Aging Neurosci. 2014 Aug 19;6:216. doi: 10.3389/fnagi.2014.00216. eCollection 2014. Review. PubMed PMID: 25191267; PubMed Central PMCID: PMC4137276. 2: Xing SH, Zhu CX, Zhang R, An L. Huperzine a in the treatment of Alzheimer's disease and vascular dementia: a meta-analysis. Evid Based Complement Alternat Med. 2014;2014:363985. doi: 10.1155/2014/363985. Epub 2014 Feb 3. Review. PubMed PMID: 24639880; PubMed Central PMCID: PMC3930088. 3: Yang G, Wang Y, Tian J, Liu JP. Huperzine A for Alzheimer's disease: a systematic review and meta-analysis of randomized clinical trials. PLoS One. 2013 Sep 23;8(9):e74916. doi: 10.1371/journal.pone.0074916. eCollection 2013. Review. PubMed PMID: 24086396; PubMed Central PMCID: PMC3781107. 4: Yue J, Dong BR, Lin X, Yang M, Wu HM, Wu T. Huperzine A for mild cognitive impairment. Cochrane Database Syst Rev. 2012 Dec 12;12:CD008827. doi: 10.1002/14651858.CD008827.pub2. Review. PubMed PMID: 23235666. 5: Ha GT, Wong RK, Zhang Y. Huperzine a as potential treatment of Alzheimer's disease: an assessment on chemistry, pharmacology, and clinical studies. Chem Biodivers. 2011 Jul;8(7):1189-204. doi: 10.1002/cbdv.201000269. Review. PubMed PMID: 21766442. 6: Hao Z, Liu M, Liu Z, Lv D. Huperzine A for vascular dementia. Cochrane Database Syst Rev. 2009 Apr 15;(2):CD007365. doi: 10.1002/14651858.CD007365.pub2. Review. PubMed PMID: 19370686; PubMed Central PMCID: PMC4171119. 7: Desilets AR, Gickas JJ, Dunican KC. Role of huperzine a in the treatment of Alzheimer's disease. Ann Pharmacother. 2009 Mar;43(3):514-8. doi: 10.1345/aph.1L402. Epub 2009 Feb 24. Review. PubMed PMID: 19240260. 8: Zhang HY, Zheng CY, Yan H, Wang ZF, Tang LL, Gao X, Tang XC. Potential therapeutic targets of huperzine A for Alzheimer's disease and vascular dementia. Chem Biol Interact. 2008 Sep 25;175(1-3):396-402. doi: 10.1016/j.cbi.2008.04.049. Epub 2008 May 13. Review. PubMed PMID: 18565502. 9: Li J, Wu HM, Zhou RL, Liu GJ, Dong BR. Huperzine A for Alzheimer's disease. Cochrane Database Syst Rev. 2008 Apr 16;(2):CD005592. doi: 10.1002/14651858.CD005592.pub2. Review. PubMed PMID: 18425924. 10: Little JT, Walsh S, Aisen PS. An update on huperzine A as a treatment for Alzheimer's disease. Expert Opin Investig Drugs. 2008 Feb;17(2):209-15. doi: 10.1517/13543784.17.2.209. Review. PubMed PMID: 18230054. 11: Li WM, Kan KK, Carlier PR, Pang YP, Han YF. East meets West in the search for Alzheimer's therapeutics - novel dimeric inhibitors from tacrine and huperzine A. Curr Alzheimer Res. 2007 Sep;4(4):386-96. Review. PubMed PMID: 17908041. 12: Zhang HY, Yan H, Tang XC. Non-cholinergic effects of huperzine A: beyond inhibition of acetylcholinesterase. Cell Mol Neurobiol. 2008 Feb;28(2):173-83. Epub 2007 Jul 27. Review. PubMed PMID: 17657601. 13: Ma X, Tan C, Zhu D, Gang DR, Xiao P. Huperzine A from Huperzia species--an ethnopharmacolgical review. J Ethnopharmacol. 2007 Aug 15;113(1):15-34. Epub 2007 Jun 2. Review. PubMed PMID: 17644292. 14: Haviv H, Wong DM, Silman I, Sussman JL. Bivalent ligands derived from Huperzine A as acetylcholinesterase inhibitors. Curr Top Med Chem. 2007;7(4):375-87. Review. PubMed PMID: 17305579. 15: Wang R, Yan H, Tang XC. Progress in studies of huperzine A, a natural cholinesterase inhibitor from Chinese herbal medicine. Acta Pharmacol Sin. 2006 Jan;27(1):1-26. Review. PubMed PMID: 16364207. 16: Wang R, Tang XC. Neuroprotective effects of huperzine A. A natural cholinesterase inhibitor for the treatment of Alzheimer's disease. Neurosignals. 2005;14(1-2):71-82. Review. PubMed PMID: 15956816. 17: Liu L, Sun JX. [Advances on study of organophosphate poisoning prevented by Huperzine A]. Wei Sheng Yan Jiu. 2005 Mar;34(2):224-6. Review. Chinese. PubMed PMID: 15952670. 18: Huperzine A. Drugs R D. 2004;5(1):44-5. Review. PubMed PMID: 14725492. 19: Jiang H, Luo X, Bai D. Progress in clinical, pharmacological, chemical and structural biological studies of huperzine A: a drug of traditional chinese medicine origin for the treatment of Alzheimer's disease. Curr Med Chem. 2003 Nov;10(21):2231-52. Review. PubMed PMID: 14529340. 20: Zangara A. The psychopharmacology of huperzine A: an alkaloid with cognitive enhancing and neuroprotective properties of interest in the treatment of Alzheimer's disease. Pharmacol Biochem Behav. 2003 Jun;75(3):675-86. Review. PubMed PMID: 12895686.