116-28-9

Basic information

• Product Name: HUPERZINE
• Synonyms: HUPERIZNE;HUPERZINE;Huperzia Serrata Extract;selagnine;Huperzia Serrata
• CAS NO: 116-28-9
• Molecular Formula: C15H18N2O
• Molecular Weight: 242.32
• EINECS: 918-088-2
• Mol File: 116-28-9.mol
• Article Data: 26

Chemical Properties

• Boiling Point: 500.6 °C at 760 mmHg
• Flash Point: 256.6 °C
• Appearance: Brown to white powder
• Density: 1.2 g/cm³
• Vapor Pressure: 3.73E-10mmHg at 25°C
• Refractive Index: 1.626
• CAS DataBase Reference: HUPERZINE(CAS DataBase Reference)
• NIST Chemistry Reference: HUPERZINE(116-28-9)
• EPA Substance Registry System: HUPERZINE(116-28-9)

Safety Data

• Hazardous Substances Data: 116-28-9(Hazardous Substances Data)

Usage

General Description

Huperzine A is a naturally occurring alkaloid compound extracted from Chinese club moss, Huperzia serrata. Renowned for its neuroprotective properties, it is commonly used as a supplement to improve memory and cognitive function. The compound’s beneficial effects are believed to result from its ability to inhibit the enzyme acetylcholinesterase, which breaks down the neurotransmitter acetylcholine - crucial for memory and learning functions. However, despite its potential benefits, Huperzine A also has certain side effects, such as nausea, diarrhea, vomiting, and others at high dose, and therefore its use requires medical supervision. Large-scale clinical trials are needed to fully determine its effect on cognitive function.

InChI:InChI=1/C15H18N2O/c1-3-11-10-6-9(2)8-15(11,16)12-4-5-14(18)17-13(12)7-10/h3-5,8,10H,6-7,16H2,1-2H3,(H,17,18)/b11-3-/t10-,15+/m0/s1

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Related news

Administration of HUPERZINE (cas 116-28-9) A exerts antidepressant-like activity in a rat model of post-stroke depression08/31/2019

Post-stroke depression (PSD) is the most common mood disorder following a stroke, and is also the main factor limiting recovery and rehabilitation in stroke patients. The present study was aimed to investigate whether Huperzine A (HupA) has antidepressant-like activity in a rat model of PSD, whi...detailed

Simultaneously preparative purification of HUPERZINE (cas 116-28-9) A and HUPERZINE (cas 116-28-9) B from Huperzia serrata by macroporous resin and preparative high performance liquid chromatography08/30/2019

Huperzine A (HupA) and Huperzine B (HupB) are natural alkaloids existed in Lycopodium plants. They both have potential clinical application for treating Alzheimer's Disease (AD). For the purpose of better utilizing the limited plant resources, a quick and low cost method to separate and pur...detailed

Structural analogs of HUPERZINE (cas 116-28-9) A improve survival in guinea pigs exposed to soman08/29/2019

Chemical warfare nerve agents such as soman exert their toxic effects through an irreversible inhibition of acetylcholinesterase (AChE) and subsequently glutamatergic function, leading to uncontrolled seizures. The natural alkaloid (−)-huperzine A is a potent inhibitor of AChE and has been demon...detailed

Variations of HUPERZINE (cas 116-28-9) A content in Lycopodiaceae species from tropics08/27/2019

(−) Huperzine A is a bioactive alkaloid from Huperzia serrata (Lycopodiaceae) used for the treatment of Alzheimer's disease. High yielding (−) huperzine A species is of interest for mass propagation since it grows slowly in temperate countries. The content of (−) huperzine A from temperate ...detailed

Abcb1a but not Abcg2 played a predominant role in limiting the brain distribution of HUPERZINE (cas 116-28-9) A in mice08/25/2019

Huperzine A has been used for improving symptoms of Alzheimer's disease. Its cholinergic side effect is thought to be an exaggerated pharmacological outcome linked to its high brain or CNS concentrations. Although Huperzine A is brain penetrable, its interaction with efflux transporters (AB...detailed

ABAD/17β-HSD10 reduction contributes to the protective mechanism of HUPERZINE (cas 116-28-9) a on the cerebral mitochondrial function in APP/PS1 mice08/24/2019

Huperzine A (HupA) is a kind of Lycopodium alkaloid with potential disease-modifying qualities that has been reported to protect against β-amyloid (Aβ)-mediated mitochondrial damage in Alzheimer's disease. However, the fundamental molecular mechanism underlying the protective action of Hu...detailed

HUPERZINE (cas 116-28-9) a loaded multiparticulate disintegrating tablet: Drug release mechanism of ethyl cellulose microparticles and pharmacokinetic study08/22/2019

Huperzine A loaded multiparticulate tablet with sustained release was developed to reduce dosing frequency and increase swallowing. The sustained release was provided by the ethyl cellulose/Poloxamer 127 (EC/F127) microparticles (MPs). F127 was added to facilitate drug release of EC MPs, and the...detailed

Relevant articles and documents

An improved synthetic route to huperzine A; New analogues and their inhibition of acetylcholinesterase

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Synthesis and biological evaluation of (±)-Z-huperzine A

The synthesis of (±)-Z-huperzine A has been accomplished and the ability of this agent to inhibit acetylcholinesterase has been measured. The compound has an IC50 of 6 × 10-6 M, which is comparable to that of huperzine B.

Synthetic method of huperzine A

The invention belongs to the technical field of medicine synthesis and particularly relates to a synthetic method of huperzine A. The method includes twelve steps of reactions, 1,4-dioxaspiro[4.5]decan-8-one being a raw material, so that the chemical synthesis of the huperzine A is completed at a high total yield. The method is fewer in reaction steps, is simple in operations, has high yield, is stable in intermediates and gentle in reaction conditions, and is easy to control in reactions.

PREPARATION OF (-)-HUPERZINE A

The present invention relates to a method for preparing (?)-huperzine A. The method involves: allowing a mixture of (±)-huperzine A obtained from chemical synthesis and a chiral acid to form (±)-huperzine A chiral acid salt under suitable conditions; recrystallizing the chiral acid salt from an organic solvent and basifying with an alkali to obtain optically pure (?)-huperzine A. The method is convenient to operate and suitable for industrial production. The chemical purity and optical purity of (?)-huperzine A obtained by the method are each greater than 99.5%, satisfying the requirement for raw pharmaceutical purity in the pharmaceutical industry.

Divergent total synthesis of the lycopodium alkaloids huperzine A, huperzine B, and huperzine U

Huperzine A, huperzine B, and huperzine U are congeners isolated from the Chinese herb Huperzia serrata (=Lycopodium serratum) in minuscule amounts. The most efficient total synthesis of huperzine A, the first asymmetric total syntheses of huperzine B, and the first total synthesis of huperzine U have been achieved efficiently in overall yields of 17%, 10%, and 9%, respectively, each spanning 10-13 steps from (R)-pulegone. The featured steps include palladium-catalyzed Buchwald-Hartwig coupling and Heck cyclization reactions and an Ir-catalyzed olefin isomerization reaction. This work has established the absolute configurations of huperzine B and huperzine U and revealed that natural huperzine A, huperzine B, and huperzine U possess the same set of absolute stereochemistries, thus providing support for the potential role of huperzine B and huperzine U in the biosynthesis of huperzine A.