Vincamine

Preparation

A method for preparing Vincamine, the method comprising the following steps:

1) Preparation of taponin: Taponin hydrochloride is freed in petroleum ether using concentrated ammonia, and then an acid salt solution is added to remove the remaining ammonia. After the reaction is completed, the aqueous layer is extracted with petroleum ether, the organic phases are combined, the organic phases are dried with a drying agent, filtered, and the filtrate is distilled under reduced pressure to obtain taponin;

2) Preparation of Vincamine: Taponin obtained in step (1) is dissolved in an organic solvent, Pd/C is added under stirring, and the reaction is carried out under a hydrogen atmosphere and normal pressure at a certain temperature. The reaction endpoint is monitored by TLC, filtered, and the filtrate is distilled under reduced pressure to obtain Vincamine;

3) Preparation of monoperoxymaleic acid: Maleic anhydride is dissolved in N,N-dimethylformamide, 30% hydrogen peroxide is added dropwise, and the reaction is carried out after the addition is complete. After the reaction is completed, the temperature is lowered, and the solution is diluted with cold methanol for later use;

4) Preparation of Vincamine: The Vincamine obtained in step (2) was dissolved in methanol, cooled, and a certain amount of monoperoxymaleic acid obtained in step (3) was added dropwise. After the oxidation reaction was carried out for a period of time, a certain amount of monoperoxymaleic acid was added dropwise. After the addition was completed, the oxidation reaction was continued for a period of time. After the reaction was completed, a reducing agent solution was added dropwise until the starch KI test paper no longer changed color. The temperature was raised to carry out the rearrangement reaction. After the reaction was completed, the temperature was lowered to 20-30℃, and a certain amount of water and concentrated ammonia were added to adjust the pH to a certain range. The temperature was lowered to crystallize, filtered, and the filter cake was washed with methanol and water. Then, it was pulped with water at a certain temperature, filtered, and the filter cake was dried under reduced pressure to obtain Vincamine.

Description

Vincamine is an alkaloid extracted from the leaves of the Vinca minor and is a related synthetic ethyl ester of vincaminic acid. It has spasmolytic effects similar to reserpine and can potentially improve blood flow in the brain.

Chemical Properties

white to almost white fine crystalline powder

Originator

Pervancamine ,Dausse,France,1969

Uses

Vincamine is often used as a nootropic agent to combat the effects of aging, or in conjunction with other nootropics (such as piracetam) for a variety of purposes. Vincamine is a peripheral vasodilator that increases blood flow to the brain.

Definition

ChEBI: Vincamine is a vinca alkaloid, an alkaloid ester, an organic heteropentacyclic compound, a methyl ester and a hemiaminal. It has a role as an antihypertensive agent, a vasodilator agent and a metabolite. It is functionally related to an eburnamenine.

Manufacturing Process

The following route is described in US Patent 4,145,552: At ambient temperature, over a period of thirty minutes, a solution of 33.8g (0.1mol) of (-)-vincadiformine in a mixture of 140 ml of anhydrous dimethylformamide and 140 ml of anhydrous toluene is added to a suspension of 2.64 g (0.11 mol) of sodium hydride in a mixture of 200 ml of anhydrous tetrahydrofuran, 20 ml of anhydrous hexamethylphosphotriamide (EMPT) and 18.7 ml (0.14 mol) of trimethyl phosphite. When the release of hydrogen has finished (about two hours later), the solution is cooled to -10°C and then stirred under an oxygen atmosphere until absorption ceases (duration: 3 hours). Still at -10°C, 136 ml of glacial acetic acid are added, and the mixture is then left at ambient temperature for two hours. After the addition of 500 ml of 1 N sulfuric acid, the aqueous phase is isolated, reextracted with 150 ml of isopropyl ether, made alkaline with 350 ml of 11 N ammonia, then extracted 3 times with 300 ml aliquots of methylene chloride. After drying over calcium chloride and evaporating the solvent, 30.2 g of crude product are obtained which, when chromatographed on a column of silica gel (1.5 kg) yield, 9.9 g of vincamine (yield: 28%) melting point (decomp.): 250°C.

brand name

Cerebroxine;Cetal;Ocu-vinc;Oxygeron;Pervincamine;Vadicate;Vinca minor;Vincacen;Vincapront;Vincavix;Vincimax.

Therapeutic Function

Vasodilator

World Health Organization (WHO)

Vincamine, an alkaloid derived from Vinca minor, is claimed to increase cerebral circulation and utilization of oxygen. It is used in a variety of cerebral disorders and is widely marketed for this purpose.

benefits

Vincamine is a naturally occurring indole alkaloid showing antioxidant activity and has been used clinically for the prevention and treatment of cerebrovascular disorders and insufficiencies. It has been well documented that antioxidants may contribute to cancer treatment, and thus, vincamine has been investigated recently for its potential antitumor activity. Vincamine was found to show cancer cell cytotoxicity and to modulate several important proteins involved in tumor growth, including acetylcholinesterase (AChE), mitogen-activated protein kinase (MAPK), nuclear factor-κB (NF-κB), nuclear factor erythroid 2-related factor 2 (Nrf2), and T-box 3 (TBX3).

General Description

Vincamine is a monoterpenoid indole alkaloid found in the leaves of Vinca minor L., belonging to the Apocynaceae family.