Vincamine

Iupac Name：methyl (15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate

CAS No.: 1617-90-9

Molecular Weight：354.44274

Modify Date.: 2022-11-22 16:56

Introduction:

white to almost white fine crystalline powder

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 derives from an eburnamenine.|Vincamine is a monoterpenoid indole alkaloid obtained from the leaves of *Vinca minor* with a vasodilatory property. Studies indicate that vincamine increases the regional cerebral blood flow.|A major alkaloid of Vinca minor L., Apocynaceae. It has been used therapeutically as a vasodilator and antihypertensive agent, particularly in cerebrovascular disorders.

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1. Names and Identifiers

: 1.1 Name; Vincamine; 1.2 Synonyms; (+)-cis-Vincamine (12S,13aS,13bS)-13a-éthyl-12-hydroxy-2,3,5,6,12,13,13a,13b-octahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij]-1,5-naphtyridine-12-carboxylate de méthyle (3a,14b,16a)-14,15-Dihydro-14-hydroxyeburnamenine-14-carboxylic Acid Methyl Ester (3alpha,14beta,16alpha)-14,15-Dihydro-14-hydroxyeburnamenine-14-carboxylic acidmethyl ester (3alpha,14beta,16alpha)-Dihydro-14-hydroxyeburnamenine-14-carboxylic acid methyl ester (41S,12S,13aS)-methyl 14,15-Dihydro-14-hydroxyeburnamenine-14-carboxylic acid methyl ester Angiopac Decincan Eburnamenine-14-carboxylic acid, 14,15-dihydro-14-hydroxy-, methyl ester, (3a,14b,16a)- Eburnamenine-14-carboxylic acid, 14,15-dihydro-14-hydroxy-, methyl ester, (3α,14Β,16α)- EINECS 216-576-3 Equipur Methyl (12S,13aS,13bS)-13a-ethyl-12-hydroxy-2,3,5,6,12,13,13a,13b-octahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate Methyl (3α,14Β,16α)-14-hydroxy-14,15-dihydroeburnamenine-14-carboxylate methyl 14-hydroxy-14,15-dihydroeburnamenine-14-carboxylate Methyl-(12S,13aS,13bS)-13a-ethyl-12-hydroxy-2,3,5,6,12,13,13a,13b-octahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij]-1,5-naphthyridin-12-carboxylat MFCD00078054 Minorin Monorin Novicet Oxicebral Perval Pervone Vinca Vraap; View all

1.3 CAS No.: 1617-90-9

1.4 CID: 15376

1.5 EINECS(EC#): 216-576-3

1.6 Molecular Formula: C21H26N2O3 (isomer)

1.7 Inchi: 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

1.8 InChIkey: RXPRRQLKFXBCSJ-GIVPXCGWSA-N

1.9 Canonical Smiles: CCC12CCCN3C1C4=C(CC3)C5=CC=CC=C5N4C(C2)(C(=O)OC)O

1.10 Isomers Smiles: CC[C@@]12CCCN3[C@@H]1C4=C(CC3)C5=CC=CC=C5N4[C@](C2)(C(=O)OC)O

2. Properties

2.1 Density: 1.36

2.1 Melting point: 232℃ (dec.)

2.1 Boiling point: 508.9 °C at 760 mmHg

2.1 Refractive index: 1.6500 (estimate)

2.1 Flash Point: 261.6 °C

2.1 Precise Quality: 354.19400

2.1 PSA: 54.70000

2.1 logP: 2.89040

2.1 Appearance: white to almost white fine crystalline powder

2.2 Storage: Keep Cold.

2.3 Chemical Properties: white to almost white fine crystalline powder

2.4 Color/Form: Yellow crystals from acetone or methanol

2.5 Decomposition: When heated to decomposition it emits toxic fumes of /nitrogen oxides/.

2.6 pKa: 12.13±0.40(Predicted)

2.7 Water Solubility: In water, 62 mg/L @ 25 deg C /Estimated/

2.8 Spectral Properties: UV max: 225, 278 nm (logE = 4.14, 3.61)

2.9 Stability: Stable under normal temperatures and pressures.

2.10 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Usage: vasodilator

4. Safety and Handling

4.1 Symbol: GHS07

4.1 Hazard Codes: Xn

4.1 Signal Word: Warning

4.1 Risk Statements: R22

4.1 Safety Statements: S36

4.1 Octanol/Water Partition Coefficient: log Kow = 3.49 @ 25 deg C /Estimated/

4.2 Hazard Declaration: H302

4.2 RIDADR: NONH for all modes of transport

4.2 Caution Statement: P301 + P312 + P330

4.2 WGK Germany: 3

4.2 RTECS: YY8575000

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

4.3 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.; View all

4.4 Toxicity: LD50 in mice (mg/kg): 75 i.v.; >1000 s.c. (Szporny, Szász); 1000 orally (Szabo, Nagy)

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth.
Storage	none
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : in CDCl3

1H NMR : 400 MHz in CDCl3

IR : KBr disc

IR : nujol mull

Mass

7. Synthesis Route

1617-90-9Total: 64 Synthesis Route

61-54-1 223 Suppliers

1617-90-9 187 Suppliers

Literatures:
Journal of Organic Chemistry, , vol. 62, # 12 p. 3890 - 3901
Yield: null

6835-99-0 1 Suppliers

1617-90-9 187 Suppliers

Literatures:
Acta Chimica Hungarica, , vol. 128, # 1 p. 109 - 118
Yield: null

1617-90-9 187 Suppliers

Literatures:
Heterocycles, , vol. 71, # 11 p. 2347 - 2362
Yield: null

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8. Precursor and Product

precursor:

83289-22-9

89396-73-6

3389-21-7

83023-42-1

82398-60-5

77793-33-0

83348-67-8

77715-76-5

85647-38-7

78179-02-9

96861-84-6

25328-05-6

35226-43-8

61-54-1

35226-42-7

96861-83-5

6835-99-0

3247-10-7

55872-13-4

77793-34-1

1617-90-9

83220-17-1

51152-47-7

View all

product :

3382-95-4

42971-09-5

1617-90-9

9. Other Information

9.0 Henrys Law Constant: Henry's Law constant = 2X10-12 atm-cu m/mol @ 25 °C /Estimated/

9.1 Collision Cross Section: 180.9 ?2 [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

9.2 Experimental Properties: Hydroxyl radical reaction rate constant = 2.6X10-10 cu cm/molec-sec @ 25 °C /Estimated/

9.3 Interactions: Vincamine in low concentrations induced a sustained contraction of the isolated guinea pig trachealis with long latency and slow onset and, in high concentrations, it induced relaxation which was potentiated in the precontracted trachealis. ...The vincamine-induced trachealis contraction was not changed by substance P desensitization, was reduced by tetrodotoxin, nifedipine and low Ca2+ high Mg2+ solution and increased in nominally Ca2+-free solution. The vincamine-induced relaxation of precontracted trachealis was increased by guanethidine and was not affected by propranolol, high Mg2+-low Ca2+ solution and tetrodotoxin. Vincamine- and vinpocetine-induced trachealis contraction as well as vinpocetine-induced relaxation at basal tension were abolished by indomethacin.

9.4 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).; View all

9.5 Drug Warnings: ...Vincamine and vincamine derivatives, ...are able to prevent the occurrence of an edematous reaction.|In animal experiments, administration of periwinkle caused destruction of blood components, manifested as leukocytopenia, lymphocytopenia, and lowering of the a a2-, and g-globulin level.|Arrhythmia was observed in rabbits and dogs after intravenous administration of doses of 0.5 to 2.5 mg/kg bw. However, this effect was not only a function of the dose but also of the speed of the infusion. When the speed of the infusion was higher than the rate of metabolic transformation, the effect on the heart increased even up to the death of the animal. The effect was linear with the dose and was present at all speeds of infusion used.|Sedative effects were established in mice after subcutaneous administration of doses of 2.5 to 10 mg/kg bw.|Other observed effects of vincamine include cardiovascular effects (e.g. hypotension, proarrhythmogenic effect) and effects on central nervous system (sedation).; View all

9.6 Mesh: 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. (See all compounds classified as Antihypertensive Agents.)|Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)

9.7 Absorption: 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.|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.|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.|For more Absorption, Distribution and Excretion (Complete) data for VINCAMINE (6 total), please visit the HSDB record page.; View all

9.8 Metabolism: The metabolism of vincamine hydrochloride was studied in the rat after oral administration of the drug. Vincamine is almost completely metabolized, only a small fraction of the original compound being excreted in the urine. The metabolites detected in blood, urine and tissues were purified by preparative thin layer and column chromatography in several solvent systems, and analyzed by mass spectrometry. It was found that the main urinary metabolites were vincamine conjugates (sulphates and glucuronides). Two new metabolites were detected in all the biological fluids and specimens analyzed: these compounds are more polar than vincamine and their structure was characterized by mass spectrometry, I.R. and U.V. spectroscopy and confirmed by synthesis in our laboratory.[Vigano V et al; Farmaco|Vincamine is very extensively metabolised with only a small percentage of unchanged compound detectable in the urine. Radiolabel studies in rats after an oral dose of 10 mg/kg bw demonstrate the metabolic pathway of vincamine. On the one hand it is hydrolysed by the plasma esterases to the unstable vincaminic acid. The latter is quickly decarboxylised and oxidised to eburnamenine. On the other hand vincamine is hydroxylated to the major metabolite 6-beta-hydroxy-vincamine, which accounts for 40% of total urinary and biliary radioactivity, followed by 6-alpha-hydroxy-vtncamine (8%) and 6-keto-vincamine, the oxidized metabolite of both previous metabolites (about 10% of the administered dose). 6-Keto-vincamine is eliminated by conjugation. The same metabolites (hydroxy.-keto) could also be detected in the urine of rabbits, dogs and man. Within 72 hours 40% of the total radioactivity are excreted in twine and 23% in the feces.; View all

9.9 Merck: 14,9983

9.10 Chemical Properties: white to almost white fine crystalline powder

9.11 Uses: vasodilator

9.12 Biological Half Life: After intravenous injection /of vincamine hydrochloride to rats/ the pharmacokinetic parameters observed were an elimination half-life of 1.68 hours /Vincamine hydrochloride/.|The following parameters were observed /after oral administration of 20 mg/kg vincamine (base) to rats/: an elimination half-life of 1.71 hours...|After oral administration of 4 mg vincamine hydrochloride/kg bw /in dogs/ an elimination half-life of 4.5 hours (longer than for rats) and a total clearance of 0.52 1/hour were observed. /vincamine hydrochloride/|Half-life of elimination for the solution was 0.57 to 1.07 hours/for 169 mg vincamine hydrochloride and 33.81 mg vincamine hydrochloride control-released tablets respectively/.|Vincamine HCl was biopharmaceutically and pharmacokinetically evaluated. ...The terminal half-life is about 1 hour... .

9.13 Antidote: Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/|Presentation depends on the active toxic agent. In most cases, vomiting, abdominal pain, and diarrhea occur within 60 to 90 minutes of significant ingestion. With some toxins, severe gastroenteritis may result in massive fluid and electrolyte loss. ... Maintain open airway and assist ventilation if necessary. Administer supplemental oxygen. Treat coma, seizures, arrhythmias, and hypotension if they occur. Replace fluid loss caused by gastroenteritis with intravenous crystalloid solutions. ... Administer activated charcoal if available ... Gastric emptying is not necessary if activated charcoal is given promptly. /Plants and Herbal Medicines: Group 1/; View all

9.14 Human Toxicity Excerpts: /SIGNS AND SYMPTOMS/ Other observed effects of vincamine include cardiovascular effects (e.g. hypotension, proarrhythmogenic effect) and effects on central nervous system (sedation).|/CASE REPORTS/ Six patients developed ventricular arrhythmias with parenteral administration of vincamine. Direct intravenous injection was the mode of administration in 2 cases, intravenous infusion in 3 cases (one at very high dosage) and intramuscular injection in 1 case. The same signs of toxicity were observed in all patients:--5 patients had recorded attacks of "torsades de pointe", which recurred in 1 of them when the drug was restarted.--1 patient had syncope and, although an ECG was not recorded at the time, an ECG shortly afterwards showed a long QT interval and R/T ventricular extrasystoles. Symptoms were generally neurological in nature with syncope, cyanosis, and convulsions. Spontaneous regression was observed in 3 cases but in the others the drug had to be stopped and cardiopulmonary resuscitation instituted. None of our patients died of their arrhythmia.|/EPIDEMIOLOGY STUDIES/ This trial was performed to investigate the therapeutic efficacy of vincamine in the treatment of primary degenerative and vascular dementia. 152 male and female patients aged between 50 and 85 years from two psychogeriatric centers and two nursing homes were initially included in the trial and screened for eligibility. 142 patients completed the trial. ...In a 12-wk double-blind treatment either 30 mg vincamine or placebo was given twice daily. ...The therapeutic efficacy of vincamine was clearly demonstrated by confirmatory analysis as the drug was statistically significantly superior to placebo in all four target variables. The clinical relevance of the outcome was further underlined by the results of the responder analysis of the variables /Sandoz Clinical Assessment Geriatric scale/ (SCAG), /the subscale 'need for help' of the nurse's rating of geriatric patients (Beurteilungsskala fur geriatrische Patienten (Evaluation scale for geriatric patients);/ BGP) and /Short Cognitive Performance Test (Syndrom-Kurztest;/ SKT). Based on the results of this trial, it can be accepted that the therapeutic effect of vincamine is superior to placebo in patients with mild to moderate dementia of degenerative and vascular etiologies.; View all

9.15 Mesh Entry Terms: Cerebroxine

9.16 Usage: A vasodilator

10. Computational chemical data

Molecular Weight: 354.44274g/mol
Molecular Formula: C₂₁H₂₆N₂O₃
Compound Is Canonicalized: True
XLogP3-AA: 2.9
Exact Mass: 354.19434270
Monoisotopic Mass: 354.19434270
Complexity: 598
Rotatable Bond Count: 3
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 4
Topological Polar Surface Area: 54.7
Heavy Atom Count: 26
Defined Atom Stereocenter Count: 3
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceB7MAAAAAAAAAAAAAAAAAAAAWAAAAA8WLEAAAAAAFix8AAAHgAACAAADizBngYyyPMMFgCoAyTyTAKCgCAhAiAImCH4ZJgLYPLAkbGVYAhkgADbyAe42eOfgAAAAAACAAAAAAAAAAQAAAAAAAAAAA==

11. Question & Answer

Is it possible that a person can know a chemical use that they never saw just by looking at its molecular formula? Or name of it? (such as vincamine 98%) Jan 20 2022
Is it possible that a person can know a chemical use that they never saw just by looking at its molecular formula? Or name of it? (such as vincamine 98%) Molecular formula, almost never. Molecular for..
What are the differences between Vincamine and Mecobalamin? Jul 20 2021
Vincamine, as the name suggests, is a type of alkaloid extracted from the Periwinkle plant. It belongs to the indole alkaloid class and can now be semi-synthesized. Vincamine has the ability to dilate..

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