116-28-9

Usage

Uses

Used in Pharmaceutical Industry:
Huperzine A is used as a cognitive enhancer for its neuroprotective properties, helping to improve memory and cognitive function by inhibiting the enzyme acetylcholinesterase, which breaks down the neurotransmitter acetylcholine.
Used in Dietary Supplements:
Huperzine A is used as a dietary supplement to support brain health and cognitive performance, with its ability to inhibit acetylcholinesterase potentially enhancing memory and learning functions.
Used in Research:
Huperzine A is used as a research compound to study its neuroprotective effects and potential applications in the treatment of cognitive disorders, such as Alzheimer's disease, due to its ability to inhibit acetylcholinesterase and promote acetylcholine levels in the brain.

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

Upstream product

• 955117-18-7 (5R,9R,11E)-5-(3-phenylprop-2-en-1-ylideneamino)-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-5,9-methanocycloocta[b]pyridin-2(1H)-one 
• 4746-97-8 cyclohexanedione monoethylene ketal 
• 120686-09-1 2-methoxy-6-oxo-5,6,7,8-tetrahydroquinoline 
• 120685-99-6 7',8'-dihydro-2'-methoxyspiro<1,3-dioxolane-2,6'(5'H)-quinoline> 
• 120686-08-0 1',5',7',8'-tetrahydrospiro<1,3-dioxolane-2,6'(2'H)-quinolin>-2'-one 
• 123435-97-2 5,6,7,8-tetrahydro-2-methoxy-6-oxo-5-quinolinecarboxylic acid methyl ester 
• 134287-26-6 [(1S,9S)-13-Eth-(Z)-ylidene-5-methoxy-11-methyl-6-aza-tricyclo[7.3.1.0^2,7]trideca-2⁽⁷⁾,3,5,10-tetraen-1-yl]-methanol 
• 207913-51-7 (1R,9S)-10-Methanesulfonyloxy-5-methoxy-11-methyl-13-oxo-6-aza-tricyclo[7.3.1.0^2,7]trideca-2⁽⁷⁾,3,5-triene-1-carboxylic acid methyl ester 
• 191600-72-3 (5R,9S)-methyl-8-hydroxy-2-methoxy-7-methyl-11-oxo-5,6,7,8,9,10-hexahydro-5,9-methanocycloocta[b]pyridine-5-carboxylate 
• 191600-74-5 (5R,9S)-methyl-2-methoxy-7-methyl-11-oxo-5,6,9,10-tetrahydro-5,9-methanocycloocta[b]pyridine-5-carboxylate 
• 185741-71-3 (1R,9R)-5-Methoxy-11-methylene-13-oxo-6-aza-tricyclo[7.3.1.0^2,7]trideca-2⁽⁷⁾,3,5-triene-1-carboxylic acid methyl ester 
• 134875-95-9 [(1S,9S)-13-Eth-(E)-ylidene-5-methoxy-11-methyl-6-aza-tricyclo[7.3.1.0^2,7]trideca-2⁽⁷⁾,3,5,10-tetraen-1-yl]-carbamic acid methyl ester 

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 academic research and scientific papers

Development of a large-scale synthetic route to manufacture (-)-huperzine A

A safe, practical and scalable process for manufacture of (-)-huperzine A has been developed and scaled up to manufacture several hundred grams of (-)-huperzine A with chemical and optical purity of >99%. The process consists of 11 chemical stages starting from commercially available materials with only nine isolation steps and no chromatography purification. This process provides a reliable and cost-effective source of synthetic (-)-huperzine A and its derivatives for pharmaceutical and nutraceutical markets.

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.

New syntheses of rac-Huperzine A and its rac-7-ethyl-derivative. Evaluation of several Huperzine A analogues as acetylcholinesterase inhibitors

rac-Huperzine A, its rac-7-ethyl-derivative and two regioisomeric analogue have been prepared though synthetic sequences involving the elaboration of the pyridisne ring in a late stage, by reaction of an intermidiate pyrrolidine enamine with propiolamide, which gave mixtures of regioisomeric pyridone derivatives. The acetylcholinesterase inhibitory activity of these and two other recently described 11-unsubstituted huperzine A analogues was determined, the rac-7-ethyl analogue of huperzine A being the most active compound, although it is about 12-fold less active than (-)- huperzine A. (C) 2000 Elsevier Science Ltd.

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.

METHODS OF RESOLVING RACEMIC MIXTURE TO OBTAIN (-)-HUPERZINE A

A method of resolving a racemic mixture of (±) Huperzine A to (-)-Huperzine A includes: separating the (-)-Huperzine A from the racemic mixture of (±) Huperzine A by chiral high performance liquid chromatography (HPLC), the chiral HPLC being performed utilizing a mobile phase including a solution including an alcohol and one selected from dichloromethane, trichloromethane, and a mixture thereof, and the chiral HPLC being performed utilizing a chiral stationary phase including a polysaccharide derivative.

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.

Cyclobutane Synthesis and Fragmentation. A Cascade Route to the Lycopodium Alkaloid (-)-Huperzine A

An asymmetric total synthesis of the nootropic alkaloid (-)-huperzine A was completed using a cascade sequence initiated by an intramolecular aza-Prins reaction and terminated by a stereoelectronically guided fragmentation of a cyclobutylcarbinyl cation as the key step in assembling the bicyclo[3.3.1]nonene core of the natural product. Intramolecular [2 + 2]-photocycloaddition of the crotyl ether of (S)-4-hydroxycyclohex-2-enone afforded a bicyclo[4.2.0]octanone containing an embedded tetrahydrofuran in which the cyclohexanone moiety was converted to a triisopropylsilyl enol ether and functionalized as an allylic azide. The derived primary amine was acylated with α-phenylselenylacrylic acid, and the resulting amide was reacted with trimethylaluminum to give a [2 + 2]-cycloadduct, which underwent retroaldol fission to produce a fused α-phenylselenyl δ-lactam. Periodate oxidation of this lactam led directly to an α-pyridone, which was converted to a fused 2-methoxypyridine. Reductive cleavage of the activated "pyridylic" C-O bond in this tetracycle and elaboration of the resultant hydroxy ketone to a diketone was followed by chemoselective conversion of the methyl ketone in this structure to an endo isopropenyl group. Condensation of the remaining ketone with methyl carbamate in the presence of acid initiated the programmed cascade sequence and furnished a known synthetic precursor to huperzine A. Subsequent demethylation of the carbamate and the methoxypyridine, accompanied by in situ decarboxylation of the intermediate carbamic acid, gave (-)-huperzine A.

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.

A novel synthesis of (-)-huperzine A via tandem intramolecular aza-Prins cyclization-cyclobutane fragmentation

The acetylcholinesterase inhibitor (-)-huperzine A was synthesized from (S)-4-hydroxycyclohex-2-enone in 17 steps by a route that involved two cyclobutane fragmentations. The first of these employed a retro-aldol cleavage to generate the α-pyridone ring o

(--)- HUPERZINE A PROCESSES AND RELATED COMPOSITIONS AND METHODS OF TREATMENT

The invention provides (1) processes for making substantially-pure (-) huperzine A and substantially-pure (-) huperzine A derivatives; (2) compositions useful in making substantially-pure (-) huperzine A and substantially-pure (-) huperzine A derivatives; and (3) methods of treating or preventing neurological disorders using substantially-pure (-) huperzine A and substantially-pure (-) huperzine A derivatives.