Vincamine Chemical Properties

Melting point:

232 °C (dec.)(lit.)

alpha 

42.8 º (c=1 in pyridine)

Boiling point:

487.66°C (rough estimate)

Density 

1.1640 (rough estimate)

refractive index 

1.6500 (estimate)

storage temp. 

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

solubility 

Chloroform (Slightly), DMSO (Slightly)

pka

12.13±0.40(Predicted)

form 

Solid

color 

White to Off-White

optical activity

[α]23/D +42.8°, c = 1 in pyridine

Merck 

14,9983

Stability:

Hygroscopic

LogP

3.100 (est)

NIST Chemistry Reference

Vincamine(1617-90-9)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

36-26

WGK Germany 

3

RTECS 

YY8575000

HS Code 

29399990

Hazardous Substances Data

1617-90-9(Hazardous Substances Data)

Toxicity

LD50 in mice (mg/kg): 75 i.v.; >1000 s.c. (Szporny, Szász); 1000 orally (Szabo, Nagy)

MSDS

• Language:English Provider:(3aS,5S,11S)-3a-Ethyl-5-hydroxy-1,2,3,3a,4,5,10,11b-octahydro-11H-5a,11a-diaza-benzo[cd]fluoranthene-5-carboxylic acid methyl ester
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

Vincamine Usage And Synthesis

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.

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