Huperzine A | CAS#102518-79-6 | acetylcholinesterase inhibitor | NMDA receptor antagonist

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

MedKoo CAT#: 600142

CAS#: 102518-79-6

Description: 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 Â– 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

CAS# 102518-79-6

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 600142
Name: Huperzine A
CAS#: 102518-79-6
Chemical Formula: C15H18N2O
Exact Mass: 242.14
Molecular Weight: 242.322
Elemental Analysis: C, 74.35; H, 7.49; N, 11.56; O, 6.60

Price and Availability

Size	Price	Availability
100mg	USD 350	2 Weeks
250mg	USD 650	2 Weeks
500mg	USD 1050	2 Weeks
1g	USD 1850	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	60.0	247.60
	Methanol	1.0	4.13

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.

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.

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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.

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Huperzine A featured