| Identification | Back Directory | [Name]
Vincamine | [CAS]
1617-90-9 | [Synonyms]
Vinca
Vraap
Perval
Pervone
Equipur
Minorin
Monorin
Novicet
Minorine
Sostenil
Ocu-vinc
Oxygeron
Decincan
Devincan
Devinkan
Angiopac
Vincadar
Vincafor
Vincagil
Vincalen
Vincamin
Vincapan
Vincimax
Vincafarm
VINCAMINE
Oxicebral
Tripervan
NSC-91998
Vincachron
Anasclerol
Teprosilic
Vincamidol
Vincapront
Vinca-Minor
Vinkametrin
Vincafolina
Vinca-Ecobi
Vincasaunier
Vinvasaunier
VINCAMINE(P)
Arteriovinca
Pervincamine
cis-Vincamine
VINCAMINE(RG)
VINCAMINE BASE
VINCAMINE 98+%
vinodrelretard
Vinodrel retard
Vincamine(8.5%)
lpha,14beta,16.)
Anasclerol (base)
(+)-cis-Vincamine
methylvincaminate
Methyl vincaminate
Alkaloid obtained from Vinca minor
Vincamine (base and/or unspecified salts)
Methyl 14-hydroxy-14,15-dihydroeburnamenine-14-carboxylate
14,15-dihydro-14-hydroxyeburnamenine-14-carboxylicacidmethylester
14,15-DIHYDRO-14-HYDROXYBURNAMENINE-14-CARBOXYLIC ACID METHYL ESTER
Methy(3α,16α)-14,15-dihydro-14β-hydroxy-eburnamenine-14-carboxylate
14,15-Dihydro-14-hydroxyeburnamenine-14-carboxylic acid methyl ester
eburnamenine-14-carboxylicacid,14,15-dihydro-14-hydroxy-,methylester,(3a
Methyl (3alpha,14beta,16alpha)-14-hydroxy-14,15-dihydroeburnamenine-14-carboxylate
(3alpha,14beta,16alpha)-Dihydro-14-hydroxyeburnamenine-14-carboxylic acid methyl ester
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
1H-Indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine, eburnamenine-14-carboxylic acid deriv.
Eburnamine-14-carboxylic acid,14,15-dihydro-14-hydroxy-, methyl ester,3alpha,14beta,16alpha)-
Eburnamenine-14-carboxylic acid, 14,15-dihydro-14-hydroxy-, methyl ester, (3alpha,14beta,16alpha)-
(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 | [EINECS(EC#)]
216-576-3 | [Molecular Formula]
C21H26N2O3 | [MDL Number]
MFCD00078054 | [MOL File]
1617-90-9.mol | [Molecular Weight]
354.44 |
| Chemical Properties | Back Directory | [Appearance]
white to almost white fine crystalline powder | [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. ]
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 | [LogP]
3.100 (est) | [NIST Chemistry Reference]
Vincamine(1617-90-9) |
| Hazard Information | Back Directory | [Chemical Properties]
white to almost white fine crystalline powder | [Uses]
vasodilator | [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. | [Originator]
Pervancamine ,Dausse,France,1969 | [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. |
| Raw materials And Preparation Products | Back Directory | [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-->EBURNAMENINE-14-CARBOXYLIC ACID, 14,15-DIHYDRO-14-HYDROXY-, ETHYL ESTER, (3A,14B,16A)- |
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