14,15-Dihydro-14-hydroxy-eburname-nin-14-carboxylsäure-methylester,(3 alpha, 14 beta, 16 alpha),-

Bezeichnung:14,15-Dihydro-14-hydroxy-eburname-nin-14-carboxylsäure-methylester,(3 alpha, 14 beta, 16 alpha),-

CAS-Nr1617-90-9

Englisch Name:Vincamine

CBNumberCB7344925

SummenformelC21H26N2O3

Molgewicht354.44

MOL-Datei1617-90-9.mol

Synonyma

Vincamin

14,15-Dihydro-14-hydroxy-eburname-nin-14-carboxylsäure-methylester,(3 alpha, 14 beta, 16 alpha),-

14,15-Dihydro-14-hydroxy-eburname-nin-14-carboxylsäure-methylester,(3 alpha, 14 beta, 16 alpha),- physikalisch-chemischer Eigenschaften

Schmelzpunkt	232 °C (dec.)(lit.)
alpha	42.8 º (c=1 in pyridine)
Siedepunkt	487.66°C (rough estimate)
Dichte	1.1640 (rough estimate)
Brechungsindex	1.6500 (estimate)
storage temp.	Keep in dark place,Inert atmosphere,2-8°C
Löslichkeit	Chloroform (Slightly), DMSO (Slightly)
pka	12.13±0.40(Predicted)
Aggregatzustand	Solid
Farbe	White to Off-White
Optische Rotation	[α]23/D +42.8°, c = 1 in pyridine
Merck	14,9983
Stabilität	Hygroscopic
Major Application	food and beverages
InChI	1S/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/t18-,20+,21+/m1/s1
InChIKey	RXPRRQLKFXBCSJ-GIVPXCGWSA-N
SMILES	CC[C@@]12CCCN3CCc4c(C13)n(c5ccccc45)[C@](O)(C2)C(=O)OC
LogP	3.100 (est)
NIST chemische Informationen	Vincamine(1617-90-9)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	22
S-Sätze:	36-26
WGK Germany	3
RTECS-Nr.	YY8575000
HS Code	29399990
Speicherklasse	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Oral
Giftige Stoffe Daten	1617-90-9(Hazardous Substances Data)
Toxizität	LD50 in mice (mg/kg): 75 i.v.; >1000 s.c. (Szporny, Szász); 1000 orally (Szabo, Nagy)

Gefahreninformationscode (GHS)

Vincamine Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
S-Sätze Betriebsanweisung:
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Beschreibung
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.
Chemische Eigenschaften
white to almost white fine crystalline powder
Originator
Pervancamine ,Dausse,France,1969
Verwenden
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.
Trademarks
Cerebroxine;Cetal;Ocu-vinc;Oxygeron;Pervincamine;Vadicate;Vinca minor;Vincacen;Vincapront;Vincavix;Vincimax.
Therapeutic Function
Vasodilator
Weltgesundheitsorganisation (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).
Allgemeine Beschreibung
Vincamine is a monoterpenoid indole alkaloid found in the leaves of Vinca minor L., belonging to the Apocynaceae family.

Vincamine Upstream-Materialien And Downstream Produkte

14,15-Dihydro-14-hydroxy-eburname-nin-14-carboxylsäure-methylester,(3 alpha, 14 beta, 16 alpha),- Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

1617-90-9, Vincamine Verwandte Suche:

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