Vincamine 1617-90-9

Details:

Vincamine is one of the main alkaloids in periwinkle, and is the quercetin in the monoterpene indole alkaloids. Its chemical name is (3α, 14β, 16α)-14,15-di Hydro-14-hydroxyivocenin-14-carboxylate methyl ester, white powder, soluble in acidic solution. In 1953, Schlittle and Furlenmeier separated vincamine from Chemicalbook from V.minor. In 1962, Trojanek, Mokry, Clauder, etc. determined its chemical structure. In 1968, Trojanek, Blaha, etc. determined the spatial configuration of vincamine. Naturally extracted vincamine has a dextromeric structure, and synthetic vincamine is a racemate. To a certain extent, vincamine has the functions of regulating cerebral circulation, maintaining neural homeostasis, protecting nerves and anti-oxidation.

Vincamine Basic information

Product Name:	Vincamine
Synonyms:	(+)-cis-Vincamine;(3alpha,14beta,16alpha)-14,15-Dihydro-14-hydroxyeburnamenine-14-carboxylic acidmethyl ester;(3alpha,14beta,16alpha)-Dihydro-14-hydroxyeburnamenine-14-carboxylic acid methyl ester;14,15-Dihydro-14-hydroxyeburnamenine-14-carboxylic acid methyl ester;(41S,12S,13aS)-methyl;Eburnamenine-14-carboxylic acid, 14,15-dihydro-14-hydroxy-, methyl ester, (3a,14b,16a)-;Oxicebral;Vincamine(8.5%)
CAS:	1617-90-9
MF:	C21H26N2O3
MW:	354.44
EINECS:	216-576-3
Product Categories:	Inhibitors;OXICEBRAL;Alkaloids;Biochemistry;Indole Alkaloids;API;AlkaloidAsymmetric Synthesis;Biochemicals Found in Plants;Chiral Building Blocks;Complex Molecules;Nutrition Research
Mol File:	1617-90-9.mol

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)
form	Solid
pka	12.13±0.40(Predicted)
color	White to Off-White
optical activity	[α]23/D +42.8°, c = 1 in pyridine
Merck	14,9983
Stability:	Hygroscopic
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 Information

Provider	Language
(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	English
SigmaAldrich	English
ACROS	English

Vincamine Usage And Synthesis

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

Vincamine Preparation Products And Raw materials

Raw materials	Trimethyl phosphite-->Oxygen-->Sodium hydride-->Aspidospermidine-3-carboxylic acid, 2,3-didehydro-, methyl ester, (5alpha,12beta,19alpha)--->(3alpha,16alpha)-D-homoeburnamenine-14,15-dione-->ethyl 3-{[2-(1H-indol-3-yl)ethyl]amino}propanoate-->TABERSONINE-->Methanol-->Tryptamine
Preparation Products	Vinpocetine-->methyl (3alpha,14alpha,16alpha)-14,15-dihydro-14-hydroxyeburnamenine-14-carboxylate

Function&Application

N, N-dimethylformamide is an excellent solvent for a variety of high polymers, such as polyethylene, polyvinyl chloride, polyacrylonitrile and polyamide, which is widely used in plastic film making, paint, fiber and other industries. It can also be used as a paint remover. It dissolves certain low - solubility pigments, making them characteristic of dyes. N, N - dimethylformamide can also be used as an effective reagent for the separation of non-hydrocarbon components from paraffin. The solubility of p-terephthalic acid and m-phthalic acid has good selectivity and can be separated in N, N- dimethylformamide.

 

 

 

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