(-)-Huperzine A

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(-)-Huperzine A Basic information

Huperzia serrata extract Indications Side effects Inhibition Uses

Product Name: (-)-Huperzine A

Synonyms: Huperzine-A1-5%;(5r-(5-alpha,9-beta,11e))-ydro-7-methyl;5,9-methanocycloocta(b)pyridin-2(1h)-one,5-amino-11-ethylidene-5,6,9,10-tetrah;HUPERIZINE;(-)-HUPERZINE A FROM HUPERZIA SERRATA;HuperziaSerrateP.E120786-18-7/;(5R,9R,E)-5-AMino-11-ethylidene-7-Methyl-5,6,9,10-tetrahydro-5,9-Methanocycloocta[b]pyridin-2(1H)-one;(-)-Huperzine A (HupA)

CAS: 102518-79-6

MF: C15H18N2O

MW: 242.32

EINECS: 600-320-6

Product Categories: Inhibitor;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Alkaloids;API;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Acetylcholine receptor;Nutritional Ingredients;reference substance;102518-79-6

Mol File: 102518-79-6.mol

(-)-Huperzine A Structure

(-)-Huperzine A Chemical Properties

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

solubility insoluble in H2O; ≥12.12 mg/mL in DMSO; ≥23.13 mg/mL in EtOH

pka 12.25±0.60(Predicted)

form neat

color White to Almost white

optical activity [α]/D -153±5°, c = 0.5 in methanol

LogP 0.833 (est)

CAS DataBase Reference 102518-79-6(CAS DataBase Reference)

Safety Information

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

MSDS Information

Provider Language

SigmaAldrich English

(-)-Huperzine A Usage And Synthesis

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.

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.