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42971-09-5

Basic Information
CAS No.: 42971-09-5
Name: Vinpocetine
Article Data: 21
Cas Database
Molecular Structure:
Molecular Structure of 42971-09-5 (Vinpocetine)
Formula: C22H26N2O2
Molecular Weight: 350.461
Synonyms: (+)-Apovincaminic acid ethyl ester;(+)-Vinpocetine;(+)-cis-Apovincaminic acid ethyl ester;AY 27255;Apovincaminic acid ethyl ester;Bravinton;Cavinton;Ceractin;Ethyl(+)-apovincaminate;Ethyl (+)-cis-apovincaminate;Ethyl apovincaminate;RGH4405;TCV 3B;Ultra-Vinca;Vinpocetinum;Vinporal;cis-Apovincaminic acid ethylester;
EINECS: 256-028-0
Density: 1.28 g/cm3
Melting Point: 147-153 °C dec
Boiling Point: 419.5 °C at 760 mmHg
Flash Point: 207.5 °C
Solubility: DMSO: 5 mg/mL
Appearance: White crystalline solid
Hazard Symbols: HarmfulXn
Risk Codes: 22
Safety: 36
Transport Information: N/A
PSA: 34.47000
LogP: 4.08620
Synthetic route
64-17-5

ethanol

4880-92-6

apovincamine

42971-09-5

Vinpocetine

Conditions
ConditionsYield
With titanium(IV) tetraethanolate In 1,4-dioxane for 40h; Heating;92%
141-52-6

sodium ethanolate

4880-92-6

apovincamine

42971-09-5

Vinpocetine

Conditions
ConditionsYield
In ethanol; toluene for 0.0166667h; Heating;90%
In ethanol for 1h; Temperature; Reflux; Autoclave; Industrial scale;1.93 kg
89396-73-6

3-((1S,12bS)-1-Ethyl-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-1-yl)-2-[(E)-hydroxyimino]-propionic acid ethyl ester

42971-09-5

Vinpocetine

Conditions
ConditionsYield
In ethanol; sulfuric acid for 0.5h; Heating;83%

(1R,5S,12bS)-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine-1-carbaldehyde

105-39-5

chloroacetic acid ethyl ester

42971-09-5

Vinpocetine

Conditions
ConditionsYield
With sodium ethanolate In tetrahydrofuran at -10 - -5℃; Product distribution / selectivity;79.4%
40163-56-2

14,15-dihydro-14β-hydroxy-(3α,16α)-eburnamenine-14-carboxylic acid ethyl ester

42971-09-5

Vinpocetine

Conditions
ConditionsYield
With methanesulfonic acid for 8h; Heating;79%
64-17-5

ethanol

82398-60-5

(3S,17S)-14-oxo-15-hydroxyimino-E-homoeburnane

42971-09-5

Vinpocetine

Conditions
ConditionsYield
With sulfuric acid for 5h;67.6%

(3aS,10bR,12bS)-5-Chloro-3a-ethyl-2,3,3a,4,5,11,12,12b-octahydro-1H-6,12a-diaza-indeno[7,1-cd]fluorene-5-carboxylic acid ethyl ester

42971-09-5

Vinpocetine

Conditions
ConditionsYield
In trifluoroacetic acid at 100℃; for 1h; Yield given;
64-17-5

ethanol

1617-90-9

vincamin

42971-09-5

Vinpocetine

Conditions
ConditionsYield
With aluminium trichloride; zinc(II) chloride 1.) reflux, 38 h, 2.) reflux, 8 h; Yield given. Multistep reaction;
1617-90-9

vincamin

42971-09-5

Vinpocetine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 90 percent / Ti(OEt)4 / various solvent(s) / 8 h / Heating
2: 79 percent / methanesulfonic acid / 8 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: 78 percent / AlCl3 / ethanol / 3 h / Heating
2: 92 percent / Ti(OEt)4 / dioxane / 40 h / Heating
View Scheme
85588-92-7

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

42971-09-5

Vinpocetine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 88 percent / p-toluenesulfonic acid monohydrate / toluene / 1.5 h / Heating
2: 90 percent / toluene; ethanol / 0.02 h / Heating
View Scheme
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Chemistry

Molecular Structure of Vinpocetinum (CAS NO.42971-09-5):

Empirical Formula: C22H26N2O2
Molecular Weight: 350.454
H bond acceptors: 4
H bond donors: 0
Freely Rotating Bonds: 4
Polar Surface Area: 34.47 Å2
Index of Refraction: 1.665
Molar Refractivity: 101.5 cm3
Molar Volume: 273 cm3
Surface Tension: 49 dyne/cm
Density: 1.28 g/cm3
Flash Point: 207.5 °C
Enthalpy of Vaporization: 67.32 kJ/mol
Boiling Point: 419.5 °C at 760 mmHg
Vapour Pressure: 3.02E-07 mmHg at 25°C
EINECS: 256-028-0
Melting point: 147-153 °C dec
Solubility: DMSO: 5 mg/mL
Appearance: White Crystalline Solid
Categories: Active Pharmaceutical Ingredients; All Inhibitors; Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals; Cyclic Nucleotide related

Toxicity Data With Reference

1.    

orl-rat LD50:503 mg/kg

    ARZNAD    Arzneimittel-Forschung. Drug Research. 26 (1976),1938.
2.    

ipr-rat LD50:134 mg/kg

    ARZNAD    Arzneimittel-Forschung. Drug Research. 26 (1976),1938.
3.    

ivn-rat LD50:42,600 mg/kg

    ARZNAD    Arzneimittel-Forschung. Drug Research. 26 (1976),1938.
4.    

orl-mus LD50:534 mg/kg

    ARZNAD    Arzneimittel-Forschung. Drug Research. 26 (1976),1938.
5.    

ipr-mus LD50:161 mg/kg

    ARZNAD    Arzneimittel-Forschung. Drug Research. 26 (1976),1938.
6.    

ivn-mus LD50:58,700 µg/kg

    ARZNAD    Arzneimittel-Forschung. Drug Research. 26 (1976),1938.

Safety Profile

Poison by intravenous and intraperitoneal routes. Moderately toxic by ingestion. Experimental teratogenic and reproductive effects. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes: Xn
Risk Statements: 22
22:  Harmful if swallowed 
Safety Statements: 36
36:  Wear suitable protective clothing 
WGK Germany: 3
RTECS: JW4792000

Specification

  Vinpocetinum , with CAS number of 42971-09-5, can be called Ethyl (+)-cis-apovincaminate ; Ethyl(+)-apovincaminate ; cis-Apovincaminic acid ethylester ; Apovincaminic acid ethyl ester ; (+)-cis-Apovincaminic acid ethyl ester ; 1H-Indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine,eburnamenine-14-carboxylic acid deriv ; (+)-Apovincaminic acid ethyl ester . It is a white crystalline solid, Vinpocetinum (CAS NO.42971-09-5) is used as a vasodilator.