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Vincamine(CAS No. 1617-90-9)

Vincamine C21H26N2O3 (cas 1617-90-9) Molecular Structure

1617-90-9 Structure

Identification and Related Records

【Name】
Vincamine
【CAS Registry number】
1617-90-9
【Synonyms】
Vincapan
Pervincamine
Decincan
Eburnamenine-14-carboxylic acid,14,15-dihydro-14-hydroxy-,methyl ester,(3R,14a,16R)-
Vincamidol
Perval
Methyl vincaminate
Monorin
Eburnamenine-14-carboxylic acid, 14,15-dihydro-14-hydroxy-, methyl ester, (3alpha,14beta,16alpha)-
Minorin
Vinkametrin
Vinca-Ecobi
Anasclerol
Vincimax
Eburnamenine-14-carboxylic acid, 14,15-dihydro-14-hydroxy-, methyl ester, (3.alpha.,14.beta.,16.alpha.)-
Vinca-Minor
Equipur
Minorine
【EINECS(EC#)】
216-576-3
【Molecular Formula】
C21H26N2O3 (Products with the same molecular formula)
【Molecular Weight】
354.44
【Inchi】
InChI=1/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-MNLRITNHSA-N
【Canonical SMILES】
CCC12CCCN3C1C4=C(CC3)C5=CC=CC=C5N4C(C2)(C(=O)OC)O
【Isomers smiles】
CC[C@@]12CCCN3[C@@H]1C4=C(CC3)C5=CC=CC=C5N4[C@](C2)(C(=O)OC)O
【MOL File】
1617-90-9.mol

Chemical and Physical Properties

【Appearance】
white to almost white fine crystalline powder
【Density】
1.36 g/cm3
【Melting Point】
232℃ (dec.)
【Boiling Point】
508.9 °C at 760 mmHg
【Vapour】
0mmHg at 25°C
【Flash Point】
261.6 °C
【Alpha】
42.8 º (C=1 IN PYRIDINE)
【Solubilities】
Insoluble
【Color/Form】
Yellow crystals from acetone or methanol
【Stability】
Stable under normal temperatures and pressures.
【Storage temp】
2-8°C
【Spectral properties】
UV max: 225, 278 nm (logE = 4.14, 3.61)
【Computed Properties】
Molecular Weight:354.44274 [g/mol]
Molecular Formula:C21H26N2O3
XLogP3-AA:2.9
H-Bond Donor:1
H-Bond Acceptor:4
Rotatable Bond Count:3
Exact Mass:354.194343
MonoIsotopic Mass:354.194343
Topological Polar Surface Area:54.7
Heavy Atom Count:26
Formal Charge:0
Complexity:598
Isotope Atom Count:0
Defined Atom Stereocenter Count:3
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:2
Feature 3D Donor Count:1
Feature 3D Cation Count:2
Feature 3D Hydrophobe Count:1
Feature 3D Ring Count:5
Effective Rotor Count:4.4
Conformer Sampling RMSD:0.8
CID Conformer Count:6

Safety and Handling

【Hazard Codes】
Xn:Harmful;
【Risk Statements】
R22
【Safety Statements 】
S36
【Safety】

Poison by intravenous and intraperitoneal routes. Moderately toxic by ingestion. When heated to decomposition it emits toxic fumes of NOx. Used as a vasodilator.
Hazard Codes: HarmfulXn
Risk Statements: 22
R22:Harmful if swallowed.
Safety Statements: 36
S36:Wear suitable protective clothing.
WGK Germany: 3
RTECS: YY8575000

【Specification】

  Vincamine , with CAS number of 1617-90-9, can be called Eburnamenine-14-carboxylic acid, 14,15-dihydro-14-hydroxy-, methyl ester, (3alpha,14beta,16.) ; Oligo Proanthocyanidin ; Vincasaunier ; Vincadar ; 14,15-Dihydro-14-hydroxyeburnamenine-14-carboxylic acid methyl ester ; Eburnamenine-14-carboxylic acid, 14,15-dihydro-14-hydroxy-, methyl ester, (3.alpha.,14.beta.,16.alpha.)- . It is a white to almost white fine crystalline powder, 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 (CAS NO.1617-90-9) is a peripheral vasodilator that increases blood flow to the brain. Vincamine is an indole alkaloid (specifically a tryptamine) found in the leaves of Vinca minor, comprising about 25-65% of the indole alkaloids found in Vinca minor by weight. Vincamine is also found in the species Catharanthus roseus. Vincamine can be synthesized from related alkaloids.

【Octanol/Water Partition Coefficient】
log Kow = 3.49 @ 25 deg C /Estimated/

Use and Manufacturing

【Usage】
Support cerebral metabolism by increasing blood flow to the brain.

Biomedical Effects and Toxicity

【Pharmacological Action】
- Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS.
- Drugs used to cause dilation of the blood vessels.
【Therapeutic Uses】
Periwinkle is used for circulatory disorders, cerebral circulatory impairment, support for the metabolism of the brain and its improved oxygen supply, prophylaxis of memory and concentration impairment, improvement of memory and thinking capacity, mental productivity, prevention of premature aging of brain cells, for geriatric support, as a sedative and as a blood pressure-lowering remedy, for catarrhs, feebleness, and for improvement of the immune function, for diarrhea, vaginal flux, throat aliments, tonsillitis and angina, sore throat, intestinal inflammation, toothache, dropsy, as a diuretic and blood-purifying remedy, for promotion of wound healing, as a hemostatic remedy, and a bitter principle.
Its use is recommended as a cerebral vasodilator in neonatal calves for cerebral anoxia.
/VET:/ Vincamine is widely used in human medicine to increase global and regional blood flow in patients suffering from acute or subchronic cerebral ischemia.
/VET:/ It is mostly used in combination with heptaminol (a central nervous system stimulant) and papaverine (a vasodilator).
【Biomedical Effects and Toxicity】
In a crossover study of six healthy volunteers the pharmacokinetics and the bioavailability of vincamine were studied after administration of two oral forms. All subjects received an oral dose of 60 mg vincamine. ...The drug generally follows a one-compartment kinetic model. The average value of Tmax is 1.4 +/- 0.5/hr with the tablets and 1 +/- 0.6/hr with the solution; the Cmax are, respectively, 155 +/- 82 micrograms . 1(-1) and 133 +/- 104 micrograms . 1(-1). The AUC are 443 +/- 156 micrograms . 1(-1) hr with the tablets and 315 +/- 178 micrograms . 1(-1) hr with the solution. [Millart H et al; Int J Clin Pharmacol Ther Toxicol 21 (11): 581-586 (1983)] PubMed Abstract
Vincamine HCl was biopharmaceutically and pharmacokinetically evaluated. For biopharmaceutical characterization of the drug the apparent lipoid/water partition coefficient (APC), pKa, extent of protein (bovine) binding and the erythrocyte (human) uptake were determined. Vincamine has an APC of 2.05, a pKa of 6.17, is 64% bound to plasma proteins, and is about 6% bound to erythrocytes. Because the gerbil was used as model in pharmacodynamic studies, the pharmacokinetic drug disposition was determined in this species and compared to parameters reported in the literature for other species. The terminal half-life is about 1 hour, the apparent volume of distribution 2.9 L/kg, and the total clearance is about 33.3 mL/min/kg. The parameters are comparable to other species including man. The brain concentration is about 5-fold that in plasma. A therapeutic steady state concentration for effectiveness in gerbils has been estimated to be 0.02 ug/mL. [Ritschel WA, Agrawala P; Methods Find Exp Clin Pharmacol 7 (3): 129-36 (1985)] PubMed Abstract
Pharmacokinetic parameters of vincamine in rats were measured after oral administration of 20 mg base/kg bw and intravenous injection of 10 mg vincamine hydrochloride/kg bw. After oral administration, a bioavailability of 58% was found and the concentration/time curve showed a two-compartment open model. The following parameters were observed: an elimination half-life of 1.71 hours, a t-max of 1.27 hours, a C-max of 0.87 ug/ml, a total clearance of 0.818 1/h (higher than the plasma perfusion volume, which indicates a very quick metabolism in other organs in addition to the liver), and a volume of distribution of 2.018 liters. The amount of unchanged vincamine excreted was very low with 3 to 11% in urine and 2 to 5% in bile. Vincamine is taken up in high concentrations into the different organs resulting in the following ratios: lung/plasma 21, brain/plasma 14.6, kidneys/plasma 14.3, liver/plasma 8.9, heart/plasma 7.6. However, elimination from these organs was significantly more rapid than from plasma. After intravenous injection the pharmacokinetic parameters observed were an elimination half-life of 1.68 hours, a C-max of 5.46 ug/ml, a total clearance of 0.866 1/hour, and a volume of distribution of 2.104 liters. The values for elimination half-life, volume of distribution and total clearance did not differ significantly between oral and intravenous administration.
Pharmacokinetics of vincamine in dogs also followed a two-compartment open model. Doses of 10, 20 and 40 mg intravenously showed dose-dependent half-life and clearance rate. After oral administration of 20 mg vincamine hydrochloride, bioavailability ranged between 23 and 58%. Vincamine could be detected in the urine at up to 9.5% depending on urinary pH.
The pharmacokinetics of vincamine were measured in 6 calves aged 2 weeks after an intravenous injection of 1 mg/kg bw of vincamine followed 5 days later by an intramuscular injection of 1 mg/kg bw of vincamine. This GLP study revealed a rapid and high intramuscular bioavailability, a high distribution volume and a very rapid elimination. The following parameters were found: bioavailability 75%; C-max 496 ug/L; t-max 0.47 hours, area under the curve (AUC) 757 ug.h/L; half life of elimination 2.39 hours; apparent volume of distribution 4.6 L/kg.
Pharmacokinetics were studied in humans, by using radio-labelled drug by oral route either in an aqueous solution (169 mg vincamine hydrochloride) or as control-released tablets (33.81 mg vincamine hydrochloride). Half-life of elimination for the solution was 0.57 to 1.07 hours, C-max was reached between 60 and 90 minutes after administration proving a rapid oral absorption. In another study, the amount of vincamine eliminated in the unchanged form in urine was 5.85% and 7.23% after 30 and 60 minutes respectively. Intravenous infusion of 30 or 40 mg of vincamine hydrochloride resulted in plasma levels of 0.6 to 1.0 3tg/ml. Cerebrospinal fluid concentrations were 5 to 24% of the simultaneous plasma concentrations 2 hours after a 30 mg infusion. Due to the very short elimination half-life, sustained release forms are used in human therapy.

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