(-)-Huperzine A

Iupac Name：(1R,9R)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.02,7]trideca-2(7),3,10-trien-5-one

Molecular Weight：242.31600

Modify Date.: 2022-11-25 02:24

Introduction: 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). View more+

Request For Quotation

1. Names and Identifiers

1.1 Name: (-)-Huperzine A
1.2 Synonyms: (&minus)-Huperzine A (&minus)-Selagine (-)-Huperzine A (HupA) (-)-HUPERZINE A FROM HUPERZIA SERRATA (5r-(5-alpha,9-beta,11e))-ydro-7-methyl (5R,9R,E)-5-AMino-11-ethylidene-7-Methyl-5,6,9,10-tetrahydro-5,9-Methanocycloocta[b]pyridin-2(1H)-one 3-Amino-1H-pyrazol-5-ol 3-Amino-5-pyrazolone 3H-Pyrazol-3-one, 5-amino-1,2-dihydro- 5,9-methanocycloocta(b)pyridin-2(1h)-one,5-amino-11-ethylidene-5,6,9,10-tetrah 5-Amino-1,2-dihydro-3H-pyrazol-3-one HUPERIZINE HuperziaSerrateP.E120786-18-7/ Huperzine A MFCD01714949

1.3 CAS No.: 102518-79-6

1.4 CID: 449069

1.5 EINECS(EC#): 600-320-6

1.6 Molecular Formula: C15H18N2O (isomer)

1.7 Inchi: 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)/t10-,15+/m0/s1

1.8 InChkey: ZRJBHWIHUMBLCN-ZUZCIYMTSA-N

1.9 Canonical Smiles: CC=C1C2CC3=C(C1(CC(=C2)C)N)C=CC(=O)N3

1.10 Isomers Smiles: CC=C1[C@@H]2CC3=C([C@]1(CC(=C2)C)N)C=CC(=O)N3

2. Properties

2.1 Density: 1.2 g/cm3

2.1 Melting point: 211-216oC

2.1 Boiling point: 505ºC at 760 mmHg

2.1 Refractive index: 1.626

2.1 Flash Point: 259.2ºC

2.1 Precise Quality: 242.14200

2.1 PSA: 58.88000

2.1 logP: 2.69780

2.1 Λmax: 313(EtOH)nm

2.2 Appearance: white to slight white crystaline powder

2.3 Chemical Properties: Pale Brown Solid

2.4 pKa: 12.25±0.60(Predicted)

2.5 StorageTemp: Keep in dark place,Inert atmosphere,2-8°C

3. Use and Manufacturing

3.1 Definition: ChEBI: A sesquiterpene alkaloid isolated from a club moss Huperzia serrata that has been shown to exhibit neuroprotective activity. (-)-Huperzine ASupplier

3.2 GHS Classification: Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 71 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H300 (35.21%): Fatal if swallowed [Danger Acute toxicity, oral]
H301+H311 (64.79%): Toxic if swallowed or in contact with skin [Danger Acute toxicity, oral; acute toxicity, dermal]
H301 (64.79%): Toxic if swallowed [Danger Acute toxicity, oral]
H310 (100%): Fatal in contact with skin [Danger Acute toxicity, dermal]
H315 (98.59%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (98.59%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H330 (100%): Fatal if inhaled [Danger Acute toxicity, inhalation]
H335 (98.59%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P260, P261, P262, P264, P270, P271, P280, P284, P301+P310, P302+P350, P302+P352, P304+P340, P305+P351+P338, P310, P312, P320, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P403+P233, P405, and P501

3.3 Produe Method: HPLC

3.4 Usage: 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).

4. Safety and Handling

4.1 Symbol: GHS06

4.1 Hazard Codes: T+

4.1 Signal Word: Danger

4.1 Risk Statements: R26/27/28; R36/37/38

4.1 Safety Statements: S26; S36/37/39; S45

4.1 Hazard Declaration: H300 + H310 + H330-H315-H319-H335

4.1 RIDADR: UN 1544 6.1/PG 2

4.1 Caution Statement: P260-P264-P280-P284-P301 + P310-P302 + P350

4.1 WGK Germany: 3

4.1 RTECS: PB9185700

4.1 Safety: Hazard Codes:?T+
Risk Statements: 26/27/28-36/37/38?
R26/27/28:Very toxic by inhalation, in contact with skin and if swallowed.?
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36/37/39-45?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.?
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 1544 6.1/PG 2
WGK Germany: 3
RTECS: PB9185700

4.2 Specification: ?(-)-Huperzine A , its cas register number is 102518-79-6. It also can be called?(-)-Selagine .
?

4.3 Toxicity

CHEMICAL IDENTIFICATION

RTECS NUMBER :: PB9185700

CHEMICAL NAME :: 5,9-Methanocycloocta(b)pyridin-2(1H)-one, 5-amino-11-ethylidene-5,6,9,10-tetrahydro-7- methyl-, (5R-(5-alpha,9-beta,11E))-

CAS REGISTRY NUMBER :: 102518-79-6

LAST UPDATED :: 199706

DATA ITEMS CITED :: 8

MOLECULAR FORMULA :: C15-H18-N2-O

MOLECULAR WEIGHT :: 242.35

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 15 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ZYYZEW Zhongguo Yaolixue Yu Dulixue Zazhi. (Chinese Pharmacological Society, 27 Tai-Ping Road, Beijing 100850, China) V.1- 1986- Volume(issue)/page/year: 3,246,1989

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2472 ug/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - lacrimation Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory depression

REFERENCE :: CYLPDN Zhongguo Yaoli Xuebao. Acta Pharmacologica Sinica. Chinese Journal of Pharmacology. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1980- Volume(issue)/page/year: 8,117,1987

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2500 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #5177082

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 5200 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #5177082

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1793 ug/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - lacrimation Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory depression

REFERENCE :: CYLPDN Zhongguo Yaoli Xuebao. Acta Pharmacologica Sinica. Chinese Journal of Pharmacology. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1980- Volume(issue)/page/year: 8,117,1987

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #5177082

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 630 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #5177082

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 1200 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ZYYZEW Zhongguo Yaolixue Yu Dulixue Zazhi. (Chinese Pharmacological Society, 27 Tai-Ping Road, Beijing 100850, China) V.1- 1986- Volume(issue)/page/year: 3,246,1989

View all

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Dermal, Category 2

Skin irritation, Category 2

Eye irritation, Category 2

Acute toxicity - Inhalation, Category 1

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H301+H311 Toxic if swallowed or in contact with skin H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation
Precautionary statement(s)
Prevention	P262 Do not get in eyes, on skin, or on clothing. P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection. P260 Do not breathe dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area. P284 [In case of inadequate ventilation] wear respiratory protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray.
Response	P302+P352 IF ON SKIN: Wash with plenty of water/... P310 Immediately call a POISON CENTER/doctor/\u2026 P321 Specific treatment (see ... on this label). P361+P364 Take off immediately all contaminated clothing and wash it before reuse. P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P320 Specific treatment is urgent (see ... on this label). P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.
Storage	P405 Store locked up. P403+P233 Store in a well-ventilated place. Keep container tightly closed.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

Predict 1H proton NMR

7. Other Information

7.0 Mesh: Drugs that inhibit cholinesterases. The neurotransmitter ACETYLCHOLINE is rapidly hydrolyzed, and thereby inactivated, by cholinesterases. When cholinesterases are inhibited, the action of endogenously released acetylcholine at cholinergic synapses is potentiated. Cholinesterase inhibitors are widely used clinically for their potentiation of cholinergic inputs to the gastrointestinal tract and urinary bladder, the eye, and skeletal muscles; they are also used for their effects on the heart and the central nervous system. (See all compounds classified as Cholinesterase Inhibitors.)|Drugs intended to prevent damage to the brain or spinal cord from ischemia, stroke, convulsions, or trauma. Some must be administered before the event, but others may be effective for some time after. They act by a variety of mechanisms, but often directly or indirectly minimize the damage produced by endogenous excitatory amino acids. (See all compounds classified as Neuroprotective Agents.)

7.1 Uses: Huperzine A is a new drug for the treatment of benign memory disorders that can effectively prevent cerebral neurasthenia in the middle-aged and elderly, restore cranial nerve function, and activate cranial neurotransmitters. 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).

7.2 Uses: Huperzine A is a potential therapeutic agent for Alzheimer disease that reversible alkaloid inhibitor of AChE which crosses the blood-brain barrier. It reduces cell death induced by glutamate in primary cultures derived from forebrain, hippocampus, cortex and cere.
In China, it is approved for use in the treatment of Alzheimer’s disease (AD). Huperzine A was classified as a dietary supplement by the FDA in 1997. As a nutraceutical, it is available in American health food stores or via the Internet, labeled as a memory aid.

7.3 Indications: Huperzine A is purified from Chinese club moss and has been traditionally used in China for the treatment of swelling, fever, inflammation, blood disorders, and schizophrenia. 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.

7.4 Definition: ChEBI: Huperzine A is a sesquiterpene alkaloid isolated from a club moss Huperzia serrata that has been shown to exhibit neuroprotective activity. It is also an effective inhibitor of acetylcholinesterase and has attracted interest as a therapeutic candidate for Alzheimer's disease. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor, a neuroprotective agent, a plant metabolite and a nootropic agent. It is a sesquiterpene alkaloid, a pyridone, a primary amino compound and an organic heterotricyclic compound. It is a conjugate base of a huperzine A(1+).

7.5 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.

7.6 Description: (?)-Huperzine A is a natural sesquiterpene alkaloid first isolated from Huperzia, a club moss used in Chinese medicine for its neuroprotective activity. It inhibits acetylcholinesterase (AChE) in rat cortex in vitro (IC₅₀ = 82 nM) and displays oral AChE inhibitory activity in animals. (?)-Huperzine A has potential applications in a variety of neuroprotective roles, including protection against organophosphate nerve agents and ameliorating symptoms of Alzheimer’s disease.

7.7 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.

7.8 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.

7.9 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 .

7.10 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.

7.11 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.

7.12 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.

7.13 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.

7.14 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.

7.15 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.

7.16 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.

7.17 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).

7.18 Chemical Properties: Pale Brown Solid

7.19 Uses: Reversible alkaloid inhibitor of AChE which crosses the blood-brain barrier. A potential therapeutic agent for Alzheimer’s disease. It reduces cell death induced by glutamate in primary cultures derived from forebrain, hippocampus, cortex and cerebellum of embryonic rat brain.

7.20 Uses: anticholinesterase, cognition enhancer

7.21 Uses: cognition-enhancing activity, potential Alzheimer’s therapeutic

7.22 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

7.23 Definition: ChEBI: A sesquiterpene alkaloid isolated from a club moss Huperzia serrata that has been shown to exhibit neuroprotective activity.

8. Computational chemical data

Molecular Weight: 242.31600g/mol
Molecular Formula: C₁₅H₁₈N₂O
Compound Is Canonicalized: True
XLogP3-AA: 0
Exact Mass: 242.141913202
Monoisotopic Mass: 242.141913202
Complexity: 551
Rotatable Bond Count: 0
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 2
Topological Polar Surface Area: 55.1
Heavy Atom Count: 18
Defined Atom Stereocenter Count: 2
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 1
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceBzIAAAAAAAAAAAAAAAAAAAAAAAAAAgQIAAAAAQAACAAAAAHgAQAAAADYiBgAACAALAAACIAiVSUACAAAAgAAAICAAAAEgIAAIAgQAEAAAAlACIgYMQgMAOAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==