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1617-90-9

Basic Information
CAS No.: 1617-90-9
Name: Vincamine
Article Data: 43
Molecular Structure:
Molecular Structure of 1617-90-9 (Vincamine)
Formula: C21H26N2O3
Molecular Weight: 354.449
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: 216-576-3
Density: 1.36 g/cm3
Melting Point: 232 °C (dec.)(lit.)
Boiling Point: 508.9 °C at 760 mmHg
Flash Point: 261.6 °C
Appearance: white to almost white fine crystalline powder
Hazard Symbols: HarmfulXn
Risk Codes: 22
Safety: 36
PSA: 54.70000
LogP: 2.89040
Synthetic route
142892-63-5

(+)-15α-Chloro-vincamine

1617-90-9

vincamin

Conditions
ConditionsYield
With hydrogen; potassium carbonate; triethylamine; palladium on activated charcoal In methanol for 6h; Ambient temperature;84.7%
6835-99-0

14-epivincamine

A

1617-90-9

vincamin

B

4880-92-6

apovincamine

Conditions
ConditionsYield
at 250℃; for 0.25h;A 7%
B 83%
at 20℃; for 0.25h;A 8%
B 75%
3247-10-7

(-)-vincadifformine

1617-90-9

vincamin

Conditions
ConditionsYield
Stage #1: (-)-vincadifformine With monoperoxymaleic acid In methanol at -5 - 0℃; for 6.16667h;
Stage #2: With sodium dithionate at 40℃; for 3h; Reagent/catalyst;
78.3%
66113-74-4

hydroxy-16 dehydro-1 vincadifformine

A

1617-90-9

vincamin

B

4880-88-0

vinburnine

Conditions
ConditionsYield
In toluene at 450℃; under 20 Torr;A 5%
B 70%
96861-85-7

O-methyl vincamine

A

6835-99-0

14-epivincamine

B

1617-90-9

vincamin

Conditions
ConditionsYield
With hydrogenchloride In acetone for 72h; Ambient temperature; Yields of byproduct given;A n/a
B 66%
85588-92-7

(-)-methyl 1,2,3,4,6,7,12,12bα-octahydroindolo<2,3-a>quinolizine(1β-yl) pyruvate oxime

A

6835-99-0

14-epivincamine

B

1617-90-9

vincamin

Conditions
ConditionsYield
With sodium disulfite; acetic acid In water at 90 - 92℃; for 6h; Yields of byproduct given;A n/a
B 60%
With sodium disulfite; acetic acid In water at 90 - 92℃; for 6h; Yield given. Title compound not separated from byproducts;A n/a
B 60%
With sodium disulfite; acetic acid In water at 92 - 95℃; for 5h;A 20%
B 40%
66113-74-4

hydroxy-16 dehydro-1 vincadifformine

A

6835-99-0

14-epivincamine

B

1617-90-9

vincamin

Conditions
ConditionsYield
at 150℃; for 0.25h;A 35%
B 60%
at 150℃; for 0.25h; other condition;A 35%
B 60%
In acetic acid at 20℃; for 12h;A 4 mg
B 50 mg
In acetic acid for 12h; Ambient temperature;A 4 mg
B 50 mg
75-09-2

dichloromethane

584-08-7

potassium carbonate

A

methyl 3-benzyl-4,4-diethyl-6-hydroxy-2,3,3,a4,5,6-hexahydro-1H-indolo(3,2,1-de)(1,5)naphthyridine-6-carboxylate

methyl 3-benzyl-4,4-diethyl-6-hydroxy-2,3,3,a4,5,6-hexahydro-1H-indolo(3,2,1-de)(1,5)naphthyridine-6-carboxylate

B

1617-90-9

vincamin

Conditions
ConditionsYield
With hydrogenchloride; ammonia; sodium chloride In methanolA n/a
B 58%
6835-99-0

14-epivincamine

A

1617-90-9

vincamin

B

4880-88-0

vinburnine

C

4880-92-6

apovincamine

Conditions
ConditionsYield
In toluene at 400℃; under 20 Torr;A 9%
B 47%
C 10%
3247-10-7

(-)-vincadifformine

A

6835-99-0

14-epivincamine

B

1617-90-9

vincamin

Conditions
ConditionsYield
With sodium hydroxide; oxygen; sodium acetate; rose bengal; sodium thiosulfate; acetic acid 1.) methanol, irradation, 60 min, 2.) H2O, 70 deg C, 20 min; Yield given. Multistep reaction;A n/a
B 46%
With sodium hydroxide; oxygen; sodium acetate; rose bengal; sodium thiosulfate; acetic acid 1.) methanol, irradation, 60 min, 2.) H2O; Yield given. Multistep reaction. Yields of byproduct given;
With sulfuric acid; ozone In methanol at 60℃; Yield given. Yields of byproduct given;
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Chemistry

Molecular Structure of Vincamine (CAS NO.1617-90-9):

Molecular Formula: C21H26N2O3
Molecular Weight: 354.44
CAS Registry Number: 1617-90-9
H bond acceptors: 5
H bond donors: 1
Freely Rotating Bonds: 4
Polar Surface Area: 43.7 Å2
Index of Refraction: 1.681
Molar Refractivity: 98.28 cm3
Molar Volume: 259.6 cm3
Surface Tension: 54.2 dyne/cm
Density: 1.36 g/cm3
Flash Point: 261.6 °C
Enthalpy of Vaporization: 82.06 kJ/mol
Boiling Point: 508.9 °C at 760 mmHg
Vapour Pressure: 3.53E-11 mmHg at 25°C
Melting point: 232 oC (dec.)
EINECS: 216-576-3
Storage temp: 2-8°C
Merck: 9983
Product Categories: Alkaloids;Biochemistry; Indole Alkaloids; AlkaloidAsymmetric Synthesis; Biochemicals Found in Plants; Chiral Building Blocks; Complex Molecules; Nutrition Research

Toxicity Data With Reference

1.    

ipr-rat LD50:253 mg/kg

    ARZNAD    Arzneimittel-Forschung. Drug Research. 32 (1982),601.
2.    

orl-mus LD50:1 g/kg

    ARZNAD    Arzneimittel-Forschung. Drug Research. 10 (1960),811.
3.    

ipr-mus LD50:215 mg/kg

    EJMCA5    European Journal of Medicinal Chemistry. Chimie Therapeutique. 16 (1981),191.
4.    

ivn-mus LD50:47,740 µg/kg

    AGSOA6    Agressologie. Revue Internationale de Physio-Biologie et de Pharmacologie Appliquees aux Effets de l’Agression. 19 (1978),211.

Safety Profile

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.