Huperzia serrata extract Acetylcholinesterase Indications Side effects Inhibition HPLC determination of the content of Huperzine A Uses
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(-)-Huperzine A

Huperzia serrata extract Acetylcholinesterase Indications Side effects Inhibition HPLC determination of the content of Huperzine A Uses
(-)-Huperzine A Structure
(-)-Huperzine A
  • CAS No.102518-79-6
  • Chemical Name:(-)-Huperzine A
  • CBNumber:CB9173024
  • Molecular Formula:C15H18N2O
  • Formula Weight:242.32
  • MOL File:102518-79-6.mol
(-)-Huperzine A Property
  • Melting point: :211-216oC
  • alpha  :D -147° (c = 0.36 in CH3OH) (Ayer); D24.5 -150.4° (c = 0.498 in MeOH) (Liu)
  • Boiling point: :505.0±50.0 °C(Predicted)
  • Density  :1.20±0.1 g/cm3(Predicted)
  • storage temp.  :Keep in dark place,Inert atmosphere,2-8°C
  • pka :12.25±0.60(Predicted)
  • form  :neat
  • optical activity :[α]/D -153±5°, c = 0.5 in methanol
  • CAS DataBase Reference :102518-79-6(CAS DataBase Reference)
Safety
  • Hazard Codes  :T+
  • Risk Statements  :26/27/28-36/37/38
  • Safety Statements  :26-36/37/39-45
  • RIDADR  :UN 1544 6.1/PG 2
  • WGK Germany  :3
  • RTECS  :PB9185700
  • HS Code  :29339900
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal wordDanger
  • Hazard statements H300
  • Precautionary statements
(-)-Huperzine A Price More Price(5)
  • Brand: Sigma-Aldrich
  • Product number: 42643
  • Product name : (?)-Huperzine A
  • Purity: analytical standard
  • Packaging: 25mg
  • Price: $212
  • Updated: 2020/08/18
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  • Brand: TCI Chemical
  • Product number: H1700
  • Product name : (-)-Huperzine A
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  • Updated: 2021/03/22
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  • Brand: Cayman Chemical
  • Product number: 14620
  • Product name : (-)-Huperzine A
  • Purity: ≥98%
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  • Price: $55
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  • Product name : (-)-Huperzine A
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(-)-Huperzine A Chemical Properties,Usage,Production

  • Huperzia serrata extract Huperzine A is a natural plant alkaloid that extracted from the Chinese medicine Huperzia serrata under the genus Huperzia. It is a potent, revisable and highly selective second generation of acetylcholinesterase inhibitors, with the appearance of yellow to white crystalline powder, and is freely soluble in chloroform, soluble in methanol and ethanol, slightly soluble in water, with high lipid solubility. It is a small molecule that can well penetrate the blood brain barrier, and after entering the central nervous, it distributes more in the brain's frontal lobe, temporal lobe, hippocampus and areas that are closely related to learning and memory. It has a strong inhibitory effect on acetylcholinesterase (AchE) at a low dosage, significantly increasing the content of acetylcholine (Ach) in neural synaptic cleft in the distribution area, thus enhancing neuronal excitatory transmission, strengthening the excitement of learning and memory in the brain, thereby with the function of improving cognitive function, enhancing memory retention and promoting memory reproduction. It is currently the most successful development of Alzheimer's disease (senile dementia) drugs.
    The above information is edited by the Chemicalbook of Cheng Jingmin.
  • Acetylcholinesterase AChE is an enzyme in the brain to decompose the neurotransmitter acetylcholine, responsible for function of a large number of neurons synaptic and excitability of the central nervous system. An acetylcholinesterase molecule can reduce functions of about 25000 acetylcholine molecule. Such inhibitor is often used as nerve gas agent, because too much acetylcholine in the body can cause muscle paralysis and suffocation.
    Patients with Alzheimer's disease often lack acetylcholine, because acetylcholine plays an important role in nerve stimulation, memory and learning, as well as excitement. The decrease of Acetylcholinesterase levels can release acetylcholine, making more neurons active.
  • Indications Huperzine A is a potent reversible cholinesterase inhibitor, stronger than physostigmine, neostigmine and Tacrine. When used for myasthenia gravis, the effective rate reaches to 99%.
    Clinical trials show that the product is suitable for benign memory disorders. It can improve patients’ ability in directed memory, associative learning, image memory, meaningless figure recognition and portrait retrieval,and it also can enhance normal people’s ability in learning and memory. This product also can improve memory disorders that caused by dementia and organic pathologic changes in brain.
    Clinically, Huperzine A is applicable to the treatment of the following symptoms:
    1. for the treatment and improvement of memory dysfunction in elder age, improving memory association function; for the memory deterioration caused by excessive use of the brain, improving work efficiency;
    2. for memory function deterioration associated with neurasthenia;
    3. for memory deterioration caused by cerebral vascular disorder;
    4. for memory improvement of Alzheimer's disease, and it has significant effects on improving and restoring the patient's cognitive ability, memory function and abnormal emotion behaviors;
    5. for the treatment of myasthenia gravis;
    6. for improvement of disturbance of association, low cognitive function, memory deterioration that associated with schizophrenia;
    7. for improvement of memory dysfunction associated with a variety of brain diseases and physical disorders.
  • Side effects Skin hives, abdominal pain, salivation, muscle twitching, diarrhea, and insomnia, but not common.
    Overdose can cause dizziness, nausea, gastrointestinal discomfort, chest tightness, fatigue, bradycardia and other reactions. The symptoms usually disappear on their own, and relief or disappear after stopping or reduction of the product when reacting significantly.
  • Inhibition Huperzine A has selective inhibition for true cholinesterase, and the inhibition strength is thousands of times stronger than pseudocholinesterase. The suppression mode is mixed inhibition of competitive and noncompetitive, with significant differences with pure competitive inhibitors. This product crosses the blood-brain barrier into the central nervous easily, having both central and peripheral therapeutic effects; it has a long effective time; it is well absorbed from the gastrointestinal tract; it has large safety index; it has good stability.
    The comparison result of inhibition intensity of different drugs to acetylcholinesterase (AChE): Huperzine A> physostigmine> neostigmine> Huperzine B> galantamine> galanin.
    The inhibition strength to human butyrylcholinesterase (BuChE): physostigmine> neostigmine> Huperzine A> Huperzine B.
    The functions of this product in both strengthening muscle contraction amplitude that induced by indirect electrical nerve stimulation and enhancing memory in rats are stronger than physostigmine, but its toxicity is lower than physostigmine, and it has longer duration of effectiveness.
  • HPLC determination of the content of Huperzine A [The test] Capsules that processed by extracts of Huperzia serrata (Thunb) Trev (Huperziaceae).
    1. Chromatographic conditions: Column: Alltima C18 column (4.6mm × 150mm), mobile phase: methanol-0.1mol/L ammonium acetate buffer (pH6.0) (36:64); flow rate: 0.6ml/min; detection wavelength: 308nm; column temperature: room temperature.
    2. The preparation of the reference solution: take defined amount of the reference substance of Huperzine A, add it to the mobile phase to make the reference solution with 0.005mg reference substance per ml.
    3. Preparation of sample solution: Take the contents of Huperzine A capsules (the equivalent of 0.125mg huperzine A) to a 25ml flask, and use the mobile phase to melt and dilute to volume, and shake and take it as the sample solution.
    4.Determination: take the reference and sample solution 20μl respectively and do the injection analysis.
  • Uses This product can effectively prevent the debilitating brain in elder age, restore brain function, active brain neurotransmitter substances, and it is the new drug for the treatment of benign memory impairment currently.
    Huperzine A can not only inhibite the activity of cholinesterase, but also improve cognitive function and ability of learning and memory through a variety of pharmacological mechanisms like effecting the system of free radicals, reducing expression levels of somatostatin, intracellular [Ca2+], glutamic acid content and increase calmodulin (CaM) and calmodulin messenger RNA (CaM mRNA).
  • Description Huperzine A is obtained from Huperzia serrata, which is the perennial fern. It shows activities in antipyretic, hemostasis, and dehumidification and is used for the treatment in folk of pneumonia, lung abscess, hematemesis, hematochezia, traumatic injury, etc.
  • Chemical Properties Pale Brown Solid
  • Physical properties Appearance: white crystalline powder. Bitter with hygroscopicity. Solubility: easily soluble in chloroform, soluble in methanol and ethanol, and slightly soluble in water. Melting point: 211–216?°C.
  • History In the 1980s, Chinese scholars isolated huperzine A from Lycopodiales, Huperziaceae, Phlegmariurus fordii, and Huperzia serrata (Thunb.) Trevis. At present, about 120 chemical components have been isolated and identified from the plant, including 90 lycopodium alkaloids and 32 lycopodium triterpenes. Huperzine A has the most potent inhibition on acetylcholinesterase activity, followed by huperzine B and 6β-hydroxy huperzine A.?These three compounds belong to lycodine-type lycopodium alkaloids. The full synthesis of huperzine A is complex and costly. Therefore, it is a focus to develop biotransformation or semisynthesis with other alkaloids as lead compounds on the basis of the intrinsic relationship among different kinds of alkaloids
    After the determination of chemical structure of huperzine A in 1986, it was found to be the same alkaloid as selagine separated from Lycopodium selago by Valenta in the 1960s, so it was classified as lycodine-type alkaloid. Huperzine A is a potent reversible inhibitor of AChE, and its ability to improve learning and memory has been validated in animal models. It was approved for treatment in Alzheimer’s disease (AD) in China in 1996
    Due to the high cost of extraction of huperzine A, research on its chemical synthesis has been the focus at home and abroad since 1986. It has been found that the chiral structure of huperzine A is essential for its biological activity; the inhibitory activity on AChE of natural products (-)?- huperzine A is twice as its raceme and 38–50 times as its enantiomer (+)?- huperzine A which is not a natural product, so the chemical synthesis of natural product (-)?- huperzine A has received extensive attention. The chemical preparation method of (-)?- huperzine A can be divided into asymmetric synthesis and raceme separation and is limited to a small amount preparation in laboratory for the high cost.
    Considering the difficulty of realizing unique bridge ring and amino structure of (-)?- huperzine A and achieving its full synthesis and structural modification, scientists are trying to synthesize analogues of huperzine A with simple structure and AchE inhibitory activity. It was found that the activity of spearmint huperzine A was similar to that of huperzine A, with improved selectivity and poor chemical stability. It was modified structurally to obtain ZT-1 .
  • Uses anticholinesterase, cognition enhancer
  • Uses cognition-enhancing activity, potential Alzheimer’s therapeutic
  • Uses Reversible alkaloid inhibitor of AChE which crosses the blood-brain barrier. A potential therapeutic agent for Alzheimer disease. It reduces cell death induced by glutamate in primary cultures derived from forebrain, hippocampus, cortex and cere
  • Definition ChEBI: A sesquiterpene alkaloid isolated from a club moss Huperzia serrata that has been shown to exhibit neuroprotective activity.
  • Indications It was mainly applied to age-related memory dysfunction and Alzheimer and has a good effect on improving memory function. It can be used to treat various types of Alzheimer’s disease and also myasthenia gravis.
  • Pharmacology Huperzine A has the ability to enhance learning and memory, improve spatial memory, and can be used for age-related dementia, vascular dementia, and other neurodegenerative diseases. Compared with the current anti-AD drugs, huperzine A can go through the blood-brain barrier, with a high oral bioavailability and longer time inhibition on AChE.
    As a highly selective AChE reversible inhibitor, huperzine A can inhibit AChE, reduce acetylcholine hydrolysis, and improve the level of acetylcholine in the synaptic gap. This inhibition is reversible, lasts for a long time, shows no drug dependence if repeated administration, and does not induce significant liver toxicity. X-ray diffraction results show that the direct binding of huperzine A to AChE active sites inhibits the binding of AChE to its substrate.
    In addition to the potent inhibition on AChE, huperzine A only shows a weak inhibitory effect on the butyrylcholinesterase; also protects neurons by inhibiting oxidative stress, reducing somatostatin, reducing the content of glutamate, decreasing the increased intracellular calcium, and inhibiting neuronal apoptosis; further improves AD-related cognitive function and reduces the symptoms of AD patients.
  • Clinical Use Since 1994, huperzine A has been approved for clinical use in improving memory and cognitive impairment in old patients with memory loss and dementia. A large number of domestic clinical studies have found that huperzine A shows therapeutic effect on learning and cognitive dysfunction of vascular dementia, mental retardation, and schizophrenia patients with mild adverse reactions.
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102518-79-6, (-)-Huperzine ARelated Search:
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  • 5,9-methanocycloocta(b)pyridin-2(1h)-one,5-amino-11-ethylidene-5,6,9,10-tetrah
  • HUPERIZINE
  • (-)-HUPERZINE A FROM HUPERZIA SERRATA
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  • Huperzine A, 98%, from Huperzia serrata (Thunb.) Trevis.
  • Huperzia Serrate P.E./Huperzine-A
  • (-)-HUPERZINE A (HUPERZINE A)
  • Huperzine A 102518-79-6
  • (+-)-huperzine A,Huperzine-a,Huperzine A
  • HUP, [5R-(5a,911E)]-5-Amino-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-5,9-methanocycloocta[b]pyridin-2-(1H)-one, Selagine,
  • 5,9-Methanocyclooctabpyridin-2(1H)-one, 5-amino-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-, (5R,9R,11E)-
  • HUPERZINE A 1%
  • Huperzine A ( Selagine )
  • (-)-HUPERZINE A, 99% HPLC
  • (-)-Huperzine A
  • (-)-Selagine
  • [5R-(5α,9β,11E)]-5-Amino-11-ethylidene-
  • 5,6,9,10-tetrahydro-7-methyl-5,9-methanocycloocta[b]pyridin-2(1H)-one
  • (5R,11E)-5β-Amino-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-5α,9α-methanocycloocta[b]pyridin-2(1H)-one
  • Huperizine A
  • Kimpukan A
  • SynonyMs (-)-Selagine
  • HUPERZINE A(P)
  • (-)- Hupperzine A
  • Isoselagine
  • Hupzine A
  • HupA
  • (-)-Huperzine A (Fandachem)
  • (-)-Huperzine A USP/EP/BP
  • Huperzia Serrate Plant Exrtact - Huperzine A
  • 102518-79-6
  • Inhibitor
  • chemical reagent
  • pharmaceutical intermediate
  • phytochemical
  • reference standards from Chinese medicinal herbs (TCM).
  • standardized herbal extract
  • Nutritional Ingredients
  • reference substance
  • Inhibitors
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Acetylcholine receptor
  • API
  • Alkaloids