(3alpha,14beta,16alpha)-14-hydroxy-14-(methoxycarbonyl)-14,15-dihydroeburnamenin-4-ium
Vincamine
CAS: 1617-90-9
Molecular Formula: C21H26N2O3
(3alpha,14beta,16alpha)-14-hydroxy-14-(methoxycarbonyl)-14,15-dihydroeburnamenin-4-ium - Names and Identifiers
| Name | Vincamine |
| Synonyms | Oxicebral Vincamine Vincamine base (+)-cis-Vincamine (41S,12S,13aS)-methyl methyl 14-hydroxy-14,15-dihydroeburnamenine-14-carboxylate 14,15-Dihydro-14-hydroxyburnamenine-14-carboxylic acid methyl ester 14,15-Dihydro-14-hydroxyeburnamenine-14-carboxylic acid methyl ester methyl (3xi,14beta,16alpha)-14-hydroxy-14,15-dihydroeburnamenine-14-carboxylate (3alpha,14beta,16alpha)-Dihydro-14-hydroxyeburnamenine-14-carboxylic acid methyl ester (3alpha,14beta,16alpha)-14-hydroxy-14-(methoxycarbonyl)-14,15-dihydroeburnamenin-4-ium Eburnamenine-14-carboxylic acid, 14,15-dihydro-14-hydroxy-, methyl ester, (3a,14b,16a)- (3alpha,14beta,16alpha)-14,15-Dihydro-14-hydroxyeburnamenine-14-carboxylic acidmethyl ester |
| CAS | 1617-90-9 |
| EINECS | 216-576-3 |
| InChI | InChI=1/C21H26N2O3/c1-3-20-10-6-11-22-12-9-15-14-7-4-5-8-16(14)23(17(15)18(20)22)21(25,13-20)19(24)26-2/h4-5,7-8,18,25H,3,6,9-13H2,1-2H3/p+1/t18-,20+,21+/m1/s1 |
(3alpha,14beta,16alpha)-14-hydroxy-14-(methoxycarbonyl)-14,15-dihydroeburnamenin-4-ium - Physico-chemical Properties
| Molecular Formula | C21H26N2O3 |
| Molar Mass | 354.44 |
| Density | 1.1640 (rough estimate) |
| Melting Point | 232°C (dec.)(lit.) |
| Boling Point | 487.66°C (rough estimate) |
| Specific Rotation(α) | 42.8 º (c=1 in pyridine) |
| Flash Point | 261.566°C |
| Solubility | DMSO : 25 mg/mL (70.53 mM; Need ultrasonic) |
| Vapor Presure | 0mmHg at 25°C |
| Appearance | White to nearly white fine crystalline powder |
| Color | White to Off-White |
| Merck | 14,9983 |
| pKa | 12.13±0.40(Predicted) |
| Storage Condition | Keep in dark place,Inert atmosphere,2-8°C |
| Stability | Hygroscopic |
| Refractive Index | 1.6500 (estimate) |
| MDL | MFCD00078054 |
(3alpha,14beta,16alpha)-14-hydroxy-14-(methoxycarbonyl)-14,15-dihydroeburnamenin-4-ium - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | 22 - Harmful if swallowed |
| Safety Description | S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | 3 |
| RTECS | YY8575000 |
| HS Code | 29399990 |
| Toxicity | LD50 in mice (mg/kg): 75 i.v.; >1000 s.c. (Szporny, Szász); 1000 orally (Szabo, Nagy) |
(3alpha,14beta,16alpha)-14-hydroxy-14-(methoxycarbonyl)-14,15-dihydroeburnamenin-4-ium - Reference
| Reference Show more | 1. Bai Yazhu, Zheng Zhizhong, Chen Qingzhi, et al. In vitro anti-tumor effects of four indole alkaloids in African horse bell fruit [J]. Subtropical Plant Science, 2019(3). 2. [IF = 4.157] Gao Lei et al."Quantitative imaging of natural products in fine brain regions using desorption electrospray ionization mass spectrometry imaging (DESI-MSI): uncaria alkaloids as a case study." ANALYTICAL AND BIOANALYTICAL CHEMISTRY. 2022 May;:1-9 |
(3alpha,14beta,16alpha)-14-hydroxy-14-(methoxycarbonyl)-14,15-dihydroeburnamenin-4-ium - Reference Information
| introduction | vincamine (vincamine) is a major alkaloid in vinca roseflower, and is a monoterpene indole alkaloid. Its chemical name is (3 α,14 β,16 α)-14, 15-dihydro-14-hydroxyivory nin-14-carboxylic acid methyl ester, white powder, soluble in acidic solution. In 1953 vinblastamine was isolated from V .minor by Schlittle and Furlenmeier. In 1962, Trojanek,Mokry,Clauder, etc. determined its chemical structure. In 1968, Trojanek,Blaha and others determined the spatial configuration of vincamine. The structure of naturally extracted vincamine is dextrorotatory, and the synthetic vincamine is racemate. To a certain extent, vincamine has the functions of regulating cerebral circulation, maintaining nerve dynamic balance, protecting nerves and resisting oxidation. |
| source | vincamine is an alkaloid extracted from the oleander plant Catharanthus (Vincami-norL). Currently, it can be semi-synthesized and is a cerebrovascular dilator. In addition to hydrochloride, the preparation of this product also includes tartrate and tea propane sulfonate (Teprosilate). vincamine (vincamine,VIN) belongs to the monoterpene indole alkaloids of the white wood alkaloids, can be separated from the small vinca and thin leaf mountain orange. Vincamine has the effects of lowering blood sugar, protecting liver, anti-tumor and preventing cardiovascular and cerebrovascular diseases. Although VIN is currently used as a tablet and sustained-release capsule, its complex chemical structure and lipophilic properties lead to its low water solubility and poor oral bioavailability, which greatly limits its clinical application. Cyclodextrin is widely used as a drug carrier, which can improve the water solubility and stability of drugs. |
| pharmacological action | vincamide can penetrate the blood-brain barrier, maintain and restore the oxidative catabolism of glucose in the diseased brain tissue, restore the production of lactic acid and the release of carbon dioxide to normal, thus expanding cerebral small blood vessels and improving cerebral circulation; it has no obvious effect on the blood flow of the normal brain tissue and the normal brain area of the patient's brain tissue, nor does it affect the blood circulation of the whole body; in addition, it has a slight sedative effect. |
| mechanism of action | the mechanisms of vincamine in the treatment of ischemic cerebrovascular diseases include: improving the utilization rate of oxygen and glucose in brain tissue; expanding cerebral blood vessels and improving microcirculation; blocking calcium ion slow channels and voltage-gated sodium ion channels; antioxidant; protecting nerve function. Although the above basic research is relatively complete, the evidence-based basis for the clinical application of vincamine ischemic cerebrovascular disease is slightly insufficient, and it needs to be further explored by randomized, large sample, multi-center clinical trials. Its clinical efficacy and exact mechanism of action. |
| indications | suitable for cerebrovascular sclerosis, brain insufficiency, eye, ear, nose, laryngeal vascular diseases, etc. It is especially suitable for the early manifestations of progressive brain insufficiency, such as dizziness, headache, memory loss, fatigue, and inattention. It can also be used for senile brain degeneration and its symptoms such as anxiety, aggressiveness, stress, dyskinesia, slow thinking, irritability and sphincter disorders in the elderly, as well as acute manifestations and sequelae of craniocerebral injury, such as coma after injury, consciousness disorder, hemiplegia (hemiplegia), language disorder, conscious symptoms of brain injury and arterial disease dementia. In addition, it also has a certain effect on retinal vascular sclerosis, cochlear disorders caused by blood vessels, such as dizziness and Meniere syndrome. |
| application | vincamine is suitable for cerebrovascular disorders, cerebral embolism, cerebral thrombosis and bleeding sequelae. The curative effect on cerebral arteriosclerosis is stronger than hydroergotic and papaverine, and long-term application is required to be effective. |
| preparation method | a preparation method of vincamine, the method includes the following steps: 1) preparation of itponin: in petroleum ether, dissociate itponin hydrochloride with concentrated ammonia water, then add acid salt solution to remove the remaining ammonia water, and separate the solution after the reaction is completed, the water layer is extracted with petroleum ether, and the organic phase is combined. The organic phase is dried and filtered with a desiccant. The filtrate is distilled under reduced pressure to obtain Taponin; 2) Preparation of Changchun Manfomin: The Taponin obtained in step (1) is dissolved in an organic solvent, Pd/C is added under stirring, and the reaction is carried out at a certain temperature under hydrogen atmosphere and normal pressure. TLC monitors the end point of the reaction and filters, after the filtrate is distilled under reduced pressure to obtain Changchun Manfo Ming; 3) Preparation of mono-peroxymaleic acid: In N,N-dimethylformamide, add maleic anhydride to dissolve, add 30% hydrogen peroxide dropwise, and react after dropping. After the reaction is completed, cool down and dilute with cold methanol for standby; 4) Preparation of Changchun Amine: Add the Changchun Manfo Ming obtained in step (2) to dissolve with methanol, after cooling, drop a certain amount of mono-peroxymaleic acid obtained in step (3). After the oxidation reaction for a period of time, drop a certain amount of mono-peroxymaleic acid. After dropping, continue the oxidation reaction for a period of time. After the reaction is completed, drop the reducing agent solution until the starch KI test paper no longer changes color, and the temperature is increased for rearrangement reaction. After the reaction is completed, a certain amount of water and concentrated ammonia water are added to adjust the pH to a certain range, after cooling and crystallization, filtration, the filter cake is washed with methanol and water, and then beaten with water at a certain temperature, filtration, and the filter cake is dried under reduced pressure to obtain vincamine. |
| use | medication for ischemic cerebrovascular disease this strain is an alkaloid extracted from the oleander plant Catharanthus (Vincami-norL), which can be semi-synthesized at present and is a cerebrovascular dilator. A peripheral vasodilator that increases blood flow to the brain. |
| NIST chemical information | The information is: webbook.nist.gov provides (external link) |
| toxic substance data | The information is: pubchem.ncbi.nlm.nih.gov Provide (external link) |
Last Update：2024-04-10 22:29:15
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