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42971-09-5

Basic Information
CAS No.: 42971-09-5
Name: Vinpocetine
Molecular Structure:
Molecular Structure of 42971-09-5 (Vinpocetine)
Formula: C22H26N2O2
Molecular Weight: 350.50
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:
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
23944-42-5

(-)-1β-methoxycarbonylethyl-1α-ethyl-1,2,3,4,6,7,12,12bα-octahydroindolo<2,3-a>quinolizine

42971-09-5

Vinpocetine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: tert-butyl nitrite, potassium tert-butoxide / toluene; methanol / 3 h / 40 °C
2: 88 percent / p-toluenesulfonic acid monohydrate / toluene / 1.5 h / Heating
3: 90 percent / toluene; ethanol / 0.02 h / Heating
View Scheme
Multi-step reaction with 4 steps
1: 95 percent / NaOH / aq. ethanol / 1.5 h / Heating
2: 77 percent / phosphoryl chloride / 24 h / Ambient temperature
3: tert-butyl nitrite, t-BuOK / toluene / 1 h / Ambient temperature
4: 67.6 percent / conc. H2SO4 / 5 h
View Scheme
Multi-step reaction with 3 steps
1: 60 percent / NaH / toluene / 5 h / Heating
2: tert-butyl nitrite, t-BuOK / toluene / 1 h / Ambient temperature
3: 67.6 percent / conc. H2SO4 / 5 h
View Scheme
83023-42-1

(+)-(1α-Ethyl-1,2,3,4,6,7,12,12bα-octahydro-indolo<2,3-a>quinolizin-1β-yl)-propionic acid

42971-09-5

Vinpocetine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 77 percent / phosphoryl chloride / 24 h / Ambient temperature
2: tert-butyl nitrite, t-BuOK / toluene / 1 h / Ambient temperature
3: 67.6 percent / conc. H2SO4 / 5 h
View Scheme
35226-41-6

(+)-(3S,17S)-14-oxo-E-homo-eburnane

42971-09-5

Vinpocetine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tert-butyl nitrite, t-BuOK / toluene / 1 h / Ambient temperature
2: 67.6 percent / conc. H2SO4 / 5 h
View Scheme
77793-33-0

(+/-)-1α-ethyl-1β-(2'-carboxy-2'-ethoxycarbonylethyl)-1,2,3,4,6,7,12,12bα-octahydro-indolo<2,3-a>quinolizine

42971-09-5

Vinpocetine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 72 percent / NaNO2 / H2O; acetic acid / 1 h / Ambient temperature
2: 46.5 percent / D-dibenzoyl tartaric acid/CH2Cl2 / ethanol
3: 83 percent / ethanol; H2SO4 / 0.5 h / Heating
View Scheme
85647-38-7, 85647-39-8, 86194-84-5, 89396-72-5, 89396-73-6, 101978-25-0, 105221-74-7, 105221-75-8

(+/-)-ethyl-(1,2,3,4,6,7,12,12bα-octahydro-indolo<2,3-a>quinolizin-1β-yl)pyruvate oxime

42971-09-5

Vinpocetine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 46.5 percent / D-dibenzoyl tartaric acid/CH2Cl2 / ethanol
2: 83 percent / ethanol; H2SO4 / 0.5 h / Heating
View Scheme
77793-34-1, 89396-79-2, 135266-72-7

(+/-)-1α-ethyl-1β-(2',2'-diethoxycarbonylethyl)-1,2,3,4,6,7,12,12bα-octahydro-indolo<2,3-a>quinolizine

42971-09-5

Vinpocetine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 79 percent / KOH / ethanol; H2O / 4 h / Ambient temperature
2: 72 percent / NaNO2 / H2O; acetic acid / 1 h / Ambient temperature
3: 46.5 percent / D-dibenzoyl tartaric acid/CH2Cl2 / ethanol
4: 83 percent / ethanol; H2SO4 / 0.5 h / Heating
View Scheme
73789-07-8

vincadifforminate d'ethyle

42971-09-5

Vinpocetine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-chlorosuccinimide / trifluoroacetic acid / 2 h / Ambient temperature
2: trifluoroacetic acid / 1 h / 100 °C
View Scheme
141-52-6

sodium ethanolate

1617-90-9

vincamin

42971-09-5

Vinpocetine

Conditions
ConditionsYield
With sulfuric acid; acetic acid In ethanol at 70℃; for 3h; pH=2 - 14; Reflux; Large scale;43.2 kg
141-52-6

sodium ethanolate

28152-73-0

(3α,14β,16α)-14,15-dihydro-14-hydroxyeburnamenine-14-carboxylic acid

42971-09-5

Vinpocetine

Conditions
ConditionsYield
With methanesulfonic acid; sulfuric acid In ethanol at 50 - 60℃; Temperature; Reagent/catalyst; Flow reactor; Large scale;
42971-09-5

Vinpocetine

27773-65-5

Apovincaminic acid

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane at 80℃; for 2h;98%
With sodium hydroxide In ethanol for 5h; Reflux;92.4%
With sodium hydroxide In methanol at 40℃; for 1h; Kinetics; Further Variations:; Reagents; Solvents; Temperatures; pH-values;
42971-09-5

Vinpocetine

109741-24-4

(+)-apovincaminic acid N-oxide ethyl ester

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In chloroform96.1%
42971-09-5

Vinpocetine

23173-26-4

((41S,13aS)-13a-ethyl-2,3,41,5,6,13a-hexahydro-1H-indolyl[3,2,1-de]pyridyl[3,2,1-ij][1,5]naphthyridine-12-yl)methanol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 10h; Inert atmosphere;93%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 10h;93%
With HN(CH2CH2C3H3N2Mes)2Cl2; potassium tert-butylate; hydrogen; cobalt(II) chloride In tetrahydrofuran at 100℃; under 45004.5 Torr; for 16h; Autoclave; Glovebox;78%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 0.5h; Inert atmosphere;
42971-09-5

Vinpocetine

(41S,13aS)-13a-ethyl-2,3,41,5,6,13a-hexahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-hydrazide

Conditions
ConditionsYield
With hydrazine hydrate In ethanol for 6h; Reflux;91%
Multi-step reaction with 2 steps
1.1: sodium hydroxide / 1,4-dioxane / 2 h / 80 °C
2.1: thionyl chloride / N,N-dimethyl-formamide; chloroform / 3 h / 0 °C / Reflux
2.2: 2 h / 20 °C
View Scheme
42971-09-5

Vinpocetine

108-46-3

recorcinol

C22H26N2O2*C6H6O2

Conditions
ConditionsYield
In 5,5-dimethyl-1,3-cyclohexadiene at 0 - 120℃; for 17h; Solvent; Temperature;91%
42971-09-5

Vinpocetine

1415983-13-9

2,7-seco vinpocetine

Conditions
ConditionsYield
With 3,7-bis(dimethylamino)phenothiazin-5-ium chloride trihydrate; oxygen In methanol Irradiation;74%
42971-09-5

Vinpocetine

vinpocetine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In ethanol; cyclohexane at 20℃; for 2h; Solvent;74%
With hydrogenchloride In ethanol; water; toluene
1594-58-7

nicotinamide oxime

42971-09-5

Vinpocetine

C26H25N5O

Conditions
ConditionsYield
With sodium ethanolate In ethanol for 10h; Reflux;72%
42971-09-5

Vinpocetine

142892-65-7

(+)-15α-Chloro-vincaminic acid ethyl ester

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite In water at 10 - 15℃; for 0.333333h;55%
42971-09-5

Vinpocetine

A

198214-30-1

(+)-vinpocetine-10-sulfonyl chloride

B

(+)-vinpocetine-11-sulfonyl chloride

Conditions
ConditionsYield
With chlorosulfonic acid In chloroform for 0.5h; Ambient temperature;A 43.7%
B 6.2%
42971-09-5

Vinpocetine

A

11-nitro-apovincaminic acid ethyl ester

B

9-nitro-apovincaminic acid ethyl ester

C

(-)-2,7-dihydro-7α,10-dinitro-2α-hydroxy-eburnamenine(3α,16α)-14-carboxylic acid ethyl ester

Conditions
ConditionsYield
With nitric acid In acetic acid for 0.5h; Ambient temperature;A n/a
B n/a
C 10%
42971-09-5

Vinpocetine

A

27773-65-5

Apovincaminic acid

B

40163-56-2

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

C

3α-epivincaminic acid ethyl ester

D

14-epivincaminic acid

E

4880-88-0

vinburnine

F

28152-73-0

(3α,14β,16α)-14,15-dihydro-14-hydroxyeburnamenine-14-carboxylic acid

Conditions
ConditionsYield
With hydrogenchloride at 80℃; for 336h; Product distribution; Rate constant; Thermodynamic data; ln A, Ea, ΔS<*>; degradation of vinpocetine in aqueous solutions, degradation products equilibria in solutions, effect of various pH, temperature and ionic strength, buffer catalysis, metal ion catalysis, oxygen effect, mechanism;
42971-09-5

Vinpocetine

A

57327-92-1

3α-deoxyvincaminic acid ethyl ester

B

57517-54-1

3α-deoxyepivincaminic acid ethyl ester

Conditions
ConditionsYield
With hydrogen; Rh on carbon In methanol at 25℃; under 4500.4 Torr; Yield given. Yields of byproduct given;
With hydrogen; palladium on activated charcoal In methanol at 25℃; under 4500.4 Torr; Yield given. Yields of byproduct given;
61-54-1

tryptamine

42971-09-5

Vinpocetine

A

(11aS,11bS)-11a-Ethyl-8-[2-(1H-indol-3-yl)-ethylsulfamoyl]-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester

B

(11aS,11bS)-11a-Ethyl-7-[2-(1H-indol-3-yl)-ethylsulfamoyl]-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester

Conditions
ConditionsYield
With chlorosulfonic acid 1) CHCl3, r.t., 0.5 h, 2) CHCl3, r.t.; Yield given. Multistep reaction;
108-91-8

cyclohexylamine

42971-09-5

Vinpocetine

A

(11aS,11bS)-8-Cyclohexylsulfamoyl-11a-ethyl-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester

B

(11aS,11bS)-7-Cyclohexylsulfamoyl-11a-ethyl-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester

Conditions
ConditionsYield
With chlorosulfonic acid 1) CHCl3, r.t., 0.5 h, 2) CHCl3, r.t.; Yield given. Multistep reaction;
104-94-9

4-methoxy-aniline

42971-09-5

Vinpocetine

A

(11aS,11bS)-11a-Ethyl-8-(4-methoxy-phenylsulfamoyl)-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester

B

(11aS,11bS)-11a-Ethyl-7-(4-methoxy-phenylsulfamoyl)-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester

Conditions
ConditionsYield
With chlorosulfonic acid 1) CHCl3, r.t., 0.5 h, 2) CHCl3, r.t.; Yield given. Multistep reaction;
55-81-2

4-Methoxyphenethylamine

42971-09-5

Vinpocetine

A

(11aS,11bS)-11a-Ethyl-8-[2-(4-methoxy-phenyl)-ethylsulfamoyl]-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester

B

(11aS,11bS)-11a-Ethyl-7-[2-(4-methoxy-phenyl)-ethylsulfamoyl]-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester

Conditions
ConditionsYield
With chlorosulfonic acid 1) CHCl3, r.t., 0.5 h, 2) CHCl3, r.t.; Yield given. Multistep reaction;
109-73-9

N-butylamine

42971-09-5

Vinpocetine

A

(11aS,11bS)-8-Butylsulfamoyl-11a-ethyl-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester

B

(11aS,11bS)-7-Butylsulfamoyl-11a-ethyl-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester

Conditions
ConditionsYield
With chlorosulfonic acid 1) CHCl3, r.t., 0.5 h, 2) CHCl3, r.t.; Yield given. Multistep reaction;
100-46-9

benzylamine

42971-09-5

Vinpocetine

A

(11aS,11bS)-8-Benzylsulfamoyl-11a-ethyl-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester

B

(11aS,11bS)-7-Benzylsulfamoyl-11a-ethyl-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester

Conditions
ConditionsYield
With chlorosulfonic acid 1) CHCl3, r.t., 0.5 h, 2) CHCl3, r.t.; Yield given. Multistep reaction;
873-74-5

4-Aminobenzonitrile

42971-09-5

Vinpocetine

A

(11aS,11bS)-8-(4-Cyano-phenylsulfamoyl)-11a-ethyl-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester

B

(11aS,11bS)-7-(4-Cyano-phenylsulfamoyl)-11a-ethyl-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester

Conditions
ConditionsYield
With chlorosulfonic acid 1) CHCl3, r.t., 0.5 h, 2) CHCl3, r.t.; Yield given. Multistep reaction;
2045-79-6

o-methoxy-2-phenylethylamine

42971-09-5

Vinpocetine

A

(11aS,11bS)-11a-Ethyl-8-[2-(2-methoxy-phenyl)-ethylsulfamoyl]-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester

B

(11aS,11bS)-11a-Ethyl-7-[2-(2-methoxy-phenyl)-ethylsulfamoyl]-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester

Conditions
ConditionsYield
With chlorosulfonic acid 1) CHCl3, r.t., 0.5 h, 2) CHCl3, r.t.; Yield given. Multistep reaction;
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    English Name: Vinpocetine (Calan) Molecular formula: C22H26N2O2 Molecular weight: 350.46 CAS accession number: 42971-09-5 Improve cerebral infarction sequelae, cerebral hemorrhage sequelae, cerebral arteriosclerosis and other symptoms i

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  • High purity Various Specifications Vinpocetine CAS:42971-09-5

  • Casno:

    42971-09-5

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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.