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ChemicalBook >> CAS DataBase List >>Vincamine

Vincamine

CAS No.
1617-90-9
Chemical Name:
Vincamine
Synonyms
Vinca;Vraap;Perval;Equipur;Minorin;Monorin;Novicet;Pervone;Oxybral;Angiopac
CBNumber:
CB7344925
Molecular Formula:
C21H26N2O3
Molecular Weight:
354.44
MDL Number:
MFCD00078054
MOL File:
1617-90-9.mol
MSDS File:
SDS
Last updated:2024-11-29 14:36:51

Vincamine Properties

Melting point 232 °C (dec.)(lit.)
Boiling point 487.66°C (rough estimate)
alpha 42.8 º (c=1 in pyridine)
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)
EWG's Food Scores 1
FDA UNII 996XVD0JHT
ATC code C04AX07
NIST Chemistry Reference Vincamine(1617-90-9)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302
Precautionary statements  P264-P270-P301+P312-P501
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)
NFPA 704
0
2 0

Vincamine price More Price(47)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich Y0002124 Vincamine European Pharmacopoeia (EP) Reference Standard 1617-90-9 Y0002124 $150 2024-03-01 Buy
Sigma-Aldrich 75778 Vincamine analytical standard 1617-90-9 50mg $108 2022-05-15 Buy
TCI Chemical V0061 Vincamine >98.0%(T) 1617-90-9 1g $84 2024-03-01 Buy
TCI Chemical V0061 Vincamine >98.0%(T) 1617-90-9 5g $281 2024-03-01 Buy
Alfa Aesar J60545 Vincamine 98% 1617-90-9 1g $103 2023-06-20 Buy
Product number Packaging Price Buy
Y0002124 Y0002124 $150 Buy
75778 50mg $108 Buy
V0061 1g $84 Buy
V0061 5g $281 Buy
J60545 1g $103 Buy

Vincamine Chemical Properties,Uses,Production

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.

3247-10-7
1617-90-9
Synthesis of Vincamine from Aspidospermidine-3-carboxylic acid, 2,3-didehydro-, methyl ester, (5alpha,12beta,19alpha)-
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View Lastest Price from Vincamine manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Vincamine pictures 2024-12-20 Vincamine
1617-90-9
US $150.00 / kg 1kg 99% 500kg Hebei Zhuanglai Chemical Trading Co Ltd
Vincamine pictures 2024-12-13 Vincamine
1617-90-9
US $0.00 / Kg/Bag 1KG 98.5%-101.5% 100kg WUHAN FORTUNA CHEMICAL CO., LTD
Vincamine pictures 2024-11-22 Vincamine
1617-90-9
US $10.00 / KG 100KG 99% 100 mt Hebei Weibang Biotechnology Co., Ltd
  • Vincamine pictures
  • Vincamine
    1617-90-9
  • US $150.00 / kg
  • 99%
  • Hebei Zhuanglai Chemical Trading Co Ltd
  • Vincamine pictures
  • Vincamine
    1617-90-9
  • US $0.00 / Kg/Bag
  • 98.5%-101.5%
  • WUHAN FORTUNA CHEMICAL CO., LTD
  • Vincamine pictures
  • Vincamine
    1617-90-9
  • US $10.00 / KG
  • 99%
  • Hebei Weibang Biotechnology Co., Ltd
(+)-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 Eburnamenine-14-carboxylic acid, 14,15-dihydro-14-hydroxy-, methyl ester, (3a,14b,16a)- Oxicebral Vincamine(8.5%) VINCAMINE(P) Methyl (3alpha,14beta,16alpha)-14-hydroxy-14,15-dihydroeburnamenine-14-carboxylate Methy(3α,16α)-14,15-dihydro-14β-hydroxy-eburnamenine-14-carboxylate 14,15-dihydro-14-hydroxyeburnamenine-14-carboxylicacidmethylester 1H-Indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine, eburnamenine-14-carboxylic acid deriv. Alkaloid obtained from Vinca minor Anasclerol Anasclerol (base) Angiopac Arteriovinca cis-Vincamine Decincan Devincan Devinkan Eburnamenine-14-carboxylic acid, 14,15-dihydro-14-hydroxy-, methyl ester, (3alpha,14beta,16alpha)- eburnamenine-14-carboxylicacid,14,15-dihydro-14-hydroxy-,methylester,(3a Eburnamine-14-carboxylic acid,14,15-dihydro-14-hydroxy-, methyl ester,3alpha,14beta,16alpha)- Equipur lpha,14beta,16.) Methyl 14-hydroxy-14,15-dihydroeburnamenine-14-carboxylate Methyl vincaminate methylvincaminate Minorin Minorine Monorin VINCAMINE(RG) Vincamine (base and/or unspecified salts) (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 14,15-DIHYDRO-14-HYDROXYBURNAMENINE-14-CARBOXYLIC ACID METHYL ESTER VINCAMINE VINCAMINE BASE Teprosilic VINCAMINE 98+% Novicet NSC-91998 Ocu-vinc Oxygeron Perval Pervincamine Pervone Sostenil Tripervan Vinca Vincachron Vincadar Vinca-Ecobi Vincafarm Vincafolina Vincafor Vincagil Vincalen