(5S,9S,11E)-5-amino-11-ethylidene-7-methyl-5,6,9,10-tetrahydro-5,9-methanocycloocta[b]pyridin-2(1H)-one
Huperzine-A
CAS: 102518-79-6;120786-18-7
Molecular Formula: C15H18N2O
(5S,9S,11E)-5-amino-11-ethylidene-7-methyl-5,6,9,10-tetrahydro-5,9-methanocycloocta[b]pyridin-2(1H)-one - Names and Identifiers
| Name | Huperzine-A |
| Synonyms | Selagine HUPERIZINE Huperzine-A Huperzine A (-) Huperzine A (-)-Huperzine A (+-)-huperzine A HUPERAZINE A(SH) (-)-Huperzine A (HupA) (-)-HUPERZINE A FROM HUPERZIA SERRATA (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 (11E)-5-amino-11-ethylidene-7-methyl-5,6,9,10-tetrahydro-5,9-methanocycloocta[b]pyridin-2(1H)-one (5R,9R,E)-5-AMino-11-ethylidene-7-Methyl-5,6,9,10-tetrahydro-5,9-Methanocycloocta[b]pyridin-2(1H)-one (5S,9S,11E)-5-amino-11-ethylidene-7-methyl-5,6,9,10-tetrahydro-5,9-methanocycloocta[b]pyridin-2(1H)-one |
| CAS | 102518-79-6 120786-18-7 |
| EINECS | 600-320-6 |
| 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/h3-6,10H,7-8,16H2,1-2H3,(H,17,18)/b11-3+/t10-,15+/m0/s1 |
(5S,9S,11E)-5-amino-11-ethylidene-7-methyl-5,6,9,10-tetrahydro-5,9-methanocycloocta[b]pyridin-2(1H)-one - Physico-chemical Properties
| Molecular Formula | C15H18N2O |
| Molar Mass | 242.32 |
| Density | 1.20±0.1 g/cm3(Predicted) |
| Melting Point | 211-216oC |
| Boling Point | 505.0±50.0 °C(Predicted) |
| Specific Rotation(α) | D -147° (c = 0.36 in CH3OH) (Ayer); D24.5 -150.4° (c = 0.498 in MeOH) (Liu) |
| Solubility | Easily soluble in chloroform, soluble in methanol and ethanol, slightly soluble in water |
| Appearance | Crystallization (propanol) |
| Color | White to Almost white |
| pKa | 12.25±0.60(Predicted) |
| Storage Condition | Keep in dark place,Inert atmosphere,2-8°C |
| Refractive Index | 1.626 |
| MDL | MFCD01714949 |
| Physical and Chemical Properties | From the plant of the family of taxiaceae, Chian Tower, Huperzinaserrata(Thumb.), Trev |
| Use | Can effectively prevent the elderly brain neurasthenia, restore brain nerve function, activation of brain nerve transmission material |
(5S,9S,11E)-5-amino-11-ethylidene-7-methyl-5,6,9,10-tetrahydro-5,9-methanocycloocta[b]pyridin-2(1H)-one - Risk and Safety
| Hazard Symbols | T+ - Very toxic |
| Risk Codes | 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 Description | 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.) |
| UN IDs | UN 1544 6.1/PG 2 |
| WGK Germany | 3 |
| RTECS | PB9185700 |
| HS Code | 29339900 |
(5S,9S,11E)-5-amino-11-ethylidene-7-methyl-5,6,9,10-tetrahydro-5,9-methanocycloocta[b]pyridin-2(1H)-one - Reference
| Reference Show more | 1. Liu De, Wu Xin, Kuang Peilin. Study on Inhibitory Activity of Acetylcholinesterase in Six Tea Extracts [J]. Journal of Food Safety and Quality Testing 2018 v.9(24):141-146. 2. Ma Zhengyue, Yang Qi, Zhang Yuangong, et al. Design and Synthesis of N-Acyl -4-Phenylthiazole -2-Amine Derivatives and Study on Inhibitory Activity of Acetylcholinesterase [J]. Journal of Pharmacy 2014 049(006):813-818. 3. Tian Yunfeng, Chen Juntao, Li Junjie, et al. Design, Synthesis and Inhibitory Activity of New L-Proline Compounds on Acetylcholinesterase [J]. Journal of Pharmacy, 2015(06):719-724. 4. Chen Yuanyuan, Gao Xuan, Liu Yuanyuan, et al. Construction of Huperzine A Immunosensor with Graphene-Chitosan Modified Electrode [J]. Journal of Analytical Testing, 2018, 37(009):1014-1019. 5. Gao Xuan, Chen Yuanyuan, Liu Yuanyuan, et al. Preparation and in vitro release evaluation of huperzine A hydrogel microspheres [J]. Chemical Reagents, 2019, 41(01):18-22. 6. Shen Pengyuan, Kang Xincong, Hu Liqin, Zhang Jiayin, Liu Dongbo. Effects of histone methylation and deacetylation on the synthesis of huperzine A by the endophytic fungus of Huperzia serrata [J]. Acta Sinica, 2019,38(02):242-253. 7. Wang Jian, Zhu Pingping, Ni Guozhu, et al. Screening of Active Components of Natural Acetylcholinesterase Inhibitors from Xinjiang Mohe Tobacco by Thin Layer Chromatography [J]. China Pharmaceutical Industry, 2014(20):38-40. 8. Zhang Hongqing, Zhang Tian, Zhang Xuezhi, etc. Isolation and Identification of SNZ-12 of Huperzine A Endophytic Fungi from Huperzia serrata [J]. Research and Development of Natural Products, 2018, v.30(12):105-109. 9. Zhang Xiaoping, Ma Dalong, Meng Fangang, et al. Research on Learning and Memory and Oxidative Stress-Apoptosis of AD Rats with Xingnao Yizhi Component [J]. Chinese Journal of Hospital Pharmacy, 2019. 10. Zhang Xiaoping, Ma Dalong, Liu Fan, et al. Experimental Study of Xingnao Yizhi Component Traditional Chinese Medicine on Learning and Memory Impairment of AD Model Rats [J]. Pharmacology and Clinic of Traditional Chinese Medicine, 2018, 034(004):144-148. 11. Peng Hongmei. Study on the Mechanism of Cerebrospinal Fluid Containing Huanglian Jiedu Decoction on Apoptosis and Inflammation of BV2 Cells Induced by Aβ_(1-42) [D]. Chengdu university of traditional Chinese medicine, 2020. 12. Xu, Wumu, et al. "Bajitianwan attenuates D-galactose-induced memory impairment and bone loss through suppression of oxidative stress in aging rat model." Journal of Ethnopharmacology 261 (2020): 112992.https://doi.org/10.1016/j.jep. 2020.112992 13. [IF=3.69] Wumu Xu et al."Bajitianwan attenuates D-galactose-induced memory impairment and bone loss through suppression of oxidative stress in aging rat model."J Ethnopharmacol. 2020 Oct;261:112992 |
(5S,9S,11E)-5-amino-11-ethylidene-7-methyl-5,6,9,10-tetrahydro-5,9-methanocycloocta[b]pyridin-2(1H)-one - Standard
Authoritative Data Verified Data
This product is (5R,9R,11E)-5-amino -11-ethylene -5,8 ,9, 10-tetrahydro-7-methyl-5, 9-methylenicooctano [B] pyridin-2 (lH) -one. The content of C15H18N20 shall be 97.0% ~ 102.0% calculated as dry product.
Last Update：2024-01-02 23:10:35
(5S,9S,11E)-5-amino-11-ethylidene-7-methyl-5,6,9,10-tetrahydro-5,9-methanocycloocta[b]pyridin-2(1H)-one - Trait
Authoritative Data Verified Data
- This product is white or off-white crystalline powder; Odorless; With hygroscopicity.
- This product is soluble in methanol, soluble in ethanol, insoluble in water; Slightly soluble in 0.01mol/L hydrochloric acid solution.
Last Update：2022-01-01 11:36:08
(5S,9S,11E)-5-amino-11-ethylidene-7-methyl-5,6,9,10-tetrahydro-5,9-methanocycloocta[b]pyridin-2(1H)-one - Introduction
Pharmacological effects: It can enhance memory, improve memory impairment, improve the efficiency of mental activity, senile memory decline and Alzheimer's disease, adolescent learning disabilities and memory enhancement.
Last Update：2022-10-16 17:11:35
(5S,9S,11E)-5-amino-11-ethylidene-7-methyl-5,6,9,10-tetrahydro-5,9-methanocycloocta[b]pyridin-2(1H)-one - Differential diagnosis
Authoritative Data Verified Data
- take about 0.2mg of this product, add 5 drops of ethanol to dissolve, and add 2 drops of bismuth potassium iodide solution to generate orange yellow precipitate.
- in the chromatogram recorded under the content determination item, the retention time of the main peak of the test solution should be consistent with the retention time of the main peak of the reference solution.
- The infrared absorption spectrum of this product should be consistent with that of the control (Spectrum set 936).
Last Update：2022-01-01 11:36:08
(5S,9S,11E)-5-amino-11-ethylidene-7-methyl-5,6,9,10-tetrahydro-5,9-methanocycloocta[b]pyridin-2(1H)-one - Exam
Authoritative Data Verified Data
clarity of acidic solution
take this product 5mg, add 0.lmol/L hydrochloric acid solution 5m I dissolved, the solution should be clear.
Related substances
take this product, add 0.01mol/L hydrochloric acid solution to dissolve and make every 1 ml containing 0.lmg solution, as a test solution; Precision take the right amount, with O. 1mol/L hydrochloric acid solution was quantitatively diluted to prepare a solution containing 2.5ug per 1m = l as a control solution. According to the chromatographic conditions under the content determination item, 20 u1 of the test solution and the control solution are accurately measured and injected into the human liquid chromatograph respectively, and the chromatogram is recorded to 2 times of the retention time of the main component chromatographic peak. If there are impurity peaks in the chromatogram of the test solution, the sum of each impurity peak area shall not be greater than the main peak area of the control solution (2.5%).
loss on drying
take about 0.3g of this product and dry under reduced pressure at 80°C to constant weight. The weight loss shall not exceed 4.0% (General rule 0831).
Last Update：2022-01-01 11:36:09
(5S,9S,11E)-5-amino-11-ethylidene-7-methyl-5,6,9,10-tetrahydro-5,9-methanocycloocta[b]pyridin-2(1H)-one - Content determination
Authoritative Data Verified Data
measured by high performance liquid chromatography (General 0512).
chromatographic conditions and system suitability test
silica gel bonded with eighteen alkyl silane as filler; Phosphate buffer (take potassium dihydrogen phosphate 2.72g, add water 1000ml to dissolve, adjust pH to 2.5 with phosphoric acid)-acetonitrile (86:14) the detection wavelength was 310Nm. The number of theoretical plates is not less than 2000 calculated according to Huperzine A peak.
assay
take this product, precision weighing, add 0.0lmol/ L hydrochloric acid solution to dissolve and quantitatively dilute to make a solution containing about 40ug per lml, as a test solution, accurately, 20u1 was injected into the liquid chromatograph, and the chromatogram was recorded. Another Huperzine A reference was taken and determined by the same method. According to the external standard method to calculate the peak area, that is.
Last Update：2022-01-01 11:36:09
(5S,9S,11E)-5-amino-11-ethylidene-7-methyl-5,6,9,10-tetrahydro-5,9-methanocycloocta[b]pyridin-2(1H)-one - Category
Authoritative Data Verified Data
cholinesterase inhibitors.
Last Update：2022-01-01 11:36:10
(5S,9S,11E)-5-amino-11-ethylidene-7-methyl-5,6,9,10-tetrahydro-5,9-methanocycloocta[b]pyridin-2(1H)-one - Storage
Authoritative Data Verified Data
light shielding, sealed storage.
Last Update：2022-01-01 11:36:10
(5S,9S,11E)-5-amino-11-ethylidene-7-methyl-5,6,9,10-tetrahydro-5,9-methanocycloocta[b]pyridin-2(1H)-one - Huperzine A Tablets
Authoritative Data Verified Data
This product contains Huperzine A (C15H18N20) should be labeled the amount of 90.0% ~ 110.0%.
trait
This product is white tablet.
identification
- take an appropriate amount of the fine powder of this product (about 0.1 mg of Huperzine A), add anhydrous ethanol (3ml), dissolve Huperzine A by ultrasound, centrifuge, and add 2 drops of bismuth potassium iodide test solution to the supernatant to form orange-yellow precipitate.
- in the chromatogram recorded under the content determination item, the retention time of the main peak of the test solution should be consistent with the retention time of the main peak of the reference solution.
examination
- Related substances take this product fine powder, add 0.Olmol/L hydrochloric acid solution to dissolve Huperzine A and make a solution containing Huperzine A per 1 ml of 20, filtered, take the continued filtrate as a test solution; Precision children take appropriate children, with 0.Olmol/L hydrochloric acid solution is set and diluted to prepare a solution containing 0.8ug of Huperzine A per 1 ml, which is used as the control solution ^ As the chromatographic conditions under the content determination item, 50 u1 of the test solution and the control solution were respectively injected into the human liquid chromatograph, and the chromatogram was recorded to 2 times of the retention time of the main component peak. If there are impurity peaks in the chromatogram of the test solution, the sum of each impurity peak area shall not be greater than the main peak area of the control solution (0.2) except the chromatographic peak before the relative retention time is 4.0%.
- 1 tablet of this product was placed in a 10ml measuring flask, and an appropriate amount of 0.0lmol/L hydrochloric acid solution was added. The Olmol/L hydrochloric acid solution is diluted to the scale, shaken well, filtered, and the filtrate is taken and the content is determined according to the method under the content determination item, which shall comply with the regulations (General rule 0941).
- dissolution of this product, according to the dissolution and release determination method (General 0931 third method), with 0.100ml of 1 mol/L hydrochloric acid solution is the dissolution medium, and the rotation speed is 50 rpm, and the operation is carried out according to law. After 30 minutes, 10ml of the solution is taken, filtered, and the chromatographic conditions under the item of content determination are taken, the continuous filtrate 50 u1 was accurately measured, and human was injected into the liquid chromatograph, and the chromatogram was recorded, the dissolution medium was added to dissolve and quantitatively dilute to prepare a solution containing about 0.5ug of Huperzine A per 1 ml, which was determined by the same method. According to the external standard method, the dissolution amount of each tablet is calculated by the peak area, and the limit is 80% of the labeled amount, which shall be in accordance with the provisions.
- others shall be in accordance with the relevant provisions under the item of tablets (General rule 0101).
Content determination
Take 20 tablets of this product, precision weighing, fine grinding, precision weighing appropriate amount (equivalent to Huperzine A 100ug), put it in a 20ml measuring flask, add 0.Olmol/L hydrochloric acid solution appropriate amount, ultrasonic to dissolve Huperzine A, with 0.Olmol/L hydrochloric acid solution is diluted to the scale, shaken, filtered, and the filtrate is taken as the test solution, according to the chromatographic conditions under the item of Huperzine A content determination, precise injection of 50ul into the liquid chromatograph, record the chromatogram; Another Huperzine A reference, precise weighing, add 0.Olmol/L hydrochloric acid solution was dissolved and diluted quantitatively to prepare a solution containing 5ug per lml, which was determined by the same method. According to the external standard method to calculate the peak area, that is.
category
Same as Huperzine A.
specification
50ug
storage
It was sealed and kept in a cool and dry place.
Last Update：2022-01-01 11:36:11
(5S,9S,11E)-5-amino-11-ethylidene-7-methyl-5,6,9,10-tetrahydro-5,9-methanocycloocta[b]pyridin-2(1H)-one - Huperzine A Injection
Authoritative Data Verified Data
This product is a sterilized aqueous solution of Huperzine A. Huperzine A (C15H18N20) should be 90.0% to 110.0% of the labeled amount.
trait
This product is a clear colorless liquid.
identification
- take 1 ml of this product and add 2 drops of bismuth potassium iodide solution to generate orange yellow precipitate.
- in the chromatogram recorded under the content determination item, the retention time of the main peak of the test solution should be consistent with the retention time of the main peak of the reference solution.
examination
- the pH value should be 3.5 to 6.5 (General 0631).
- Related substances take this product and use 0.Olmol/L hydrochloric acid solution was diluted to prepare Huperzine A containing 0. 1% per 1 ml. lmg solution, as the test solution; Precision children take appropriate amount, with 0. A solution containing 2.5ug of Huperzine A per 1 ml was prepared by quantitative dilution of 1 mol/L hydrochloric acid solution as a control solution. According to the chromatographic conditions under the content determination item, 20ul of the test solution and the control solution are accurately measured, and the human liquid chromatograph is injected respectively, and the chromatogram is recorded to 2 times of the retention time of the main component peak. If there are impurity peaks in the chromatogram of the test solution, the sum of each impurity peak area shall not be greater than the main peak area of the control solution (2.5%).
- others should comply with the relevant provisions under injection (General 0102).
inclusion assay
take an appropriate amount of this product and use 0.Olmol/L hydrochloric acid solution was quantitatively diluted to prepare a solution containing Huperzine A of 40ug per 1 ml, which was obtained as a test solution according to the method under the item of Huperzine A content measurement.
category
Same as Huperzine A.
specification
lml : 0.2mg
storage
light shielding, closed storage.
Last Update：2022-01-01 11:36:12
(5S,9S,11E)-5-amino-11-ethylidene-7-methyl-5,6,9,10-tetrahydro-5,9-methanocycloocta[b]pyridin-2(1H)-one - Huperzine A Tablets
Authoritative Data Verified Data
This product contains Huperzine A (C15H18N20) should be labeled the amount of 90.0% ~ 110.0%.
trait
The content of this product is white or white particles or powder.
identification
- the content of this product is suitable for children (about equivalent to Huperzine A O. 1 mg), add anhydrous ethanol 3ml, ultrasonic dissolution of Huperzine A, centrifugation, take the solution and 2 drops of bismuth potassium iodide solution, that is, the formation of orange yellow precipitate.
- in the chromatogram recorded under the content determination item, the retention time of the main peak of the test solution should be consistent with the retention time of the main peak of the reference solution.
examination
- Related substances take an appropriate amount of the contents of this product and add O.Olmol/L hydrochloric acid solution Huperzine A was dissolved and diluted to make a solution containing Huperzine A of 20ug per 1 ml, filtered, and the continued filtrate was taken as the test solution. Olmol/L hydrochloric acid solution a solution containing 0.8ug of Huperzine A per 1 ml was prepared by diluting the solution with sodium chloride as a control solution. According to the chromatographic conditions under the content determination item, 50 u1 of the test solution and 50 u1 of the control solution are accurately measured and injected into the human liquid chromatograph respectively, and the chromatogram is recorded to 2 times of the retention time of the main component peak. If there are impurity peaks in the chromatogram of the test solution, the sum of each impurity peak area shall not be greater than the main peak area of the control solution (0.2) except the chromatographic peak before the relative retention time is 4.0%.
- Content uniformity take 1 capsule of this product, pour the contents into a 10ml expensive bottle, and use a small amount of O.Olmol/L hydrochloric acid solution to wash the capsule shell, wash into the flask, plus 0.Olmol/L hydrochloric acid solution appropriate amount, ultrasonic to dissolve Huperzine A, with 0. The Olmol/L gold acid solution is diluted to the scale, shaken well, filtered, and the filtrate is taken and the content is determined according to the method under the item containing children's determination, which shall comply with the regulations (General rule 0941).
- dissolution of this product, according to the dissolution and release determination method (General 0931 third method), with 0.100ml of 1 mol/L hydrochloric acid solution was used as the dissolution medium, the rotation speed was 35 revolutions per minute, and the operation was carried out according to law. After 30 minutes, 10ml of the solution was taken and filtered. According to the chromatographic conditions under the content determination item, the filtrate 50 u1 was accurately measured and injected into the human liquid chromatograph, and the chromatogram was recorded, the dissolution medium is added to dissolve and quantitatively dilute to prepare a solution containing about 0.5ug per 1 ml, which is determined by the same method, and the dissolution amount of each particle is calculated by the peak area according to the external standard method. The limit is 75% of the labeled amount and shall be in accordance with the provisions.
- others should comply with the relevant provisions under the capsule (General 0103).
Content determination
take the contents of 20 capsules of this product, precise weighing, fine grinding, precise weighing appropriate amount (approximately equivalent to Huperzine A 100ug), put it in a 20ml measuring flask, and add O.Olmol/L hydrochloric acid solution appropriate amount, ultrasonic dissolution of Huperzine A, with O.Olmol/L hydrochloric acid solution is diluted to the scale, shaken, filtered, and the filtrate is taken as the test solution, according to the chromatographic conditions under the item of Huperzine A content determination, 50u1 was injected into the liquid chromatograph for precise measurement, and the chromatogram was recorded. Olmol/L hydrochloric acid solution was dissolved and diluted quantitatively to prepare a solution containing 5ug per lml, which was determined by the same method. According to the external standard method to calculate the peak area, that is.
category
Same as Huperzine A.
specification
50ug
storage
shade, seal, and store in a cool and dry place.
Last Update：2022-01-01 11:36:13
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