Vinpocetine supplier | CasNO.42971-09-5

Name
Vinpocetine
EINECS 256-028-0
CAS No. 42971-09-5
Article Data21
CAS DataBase
Density 1.28 g/cm³
Solubility DMSO: 5 mg/mL
Melting Point 147-153 °C dec
Formula C₂₂H₂₆N₂O₂
Boiling Point 419.5 °C at 760 mmHg
Molecular Weight 350.461
Flash Point 207.5 °C
Transport Information
Appearance White crystalline solid
Safety 36
Risk Codes 22
Molecular Structure
Hazard Symbols Xn
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;
PSA 34.47000
LogP 4.08620

Synthetic route

: 64-17-5
ethanol

: 4880-92-6
apovincamine

: 42971-09-5
Vinpocetine

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
In trifluoroacetic acid at 100℃; for 1h; Yield given;

: 64-17-5
ethanol

: 1617-90-9
vincamin

: 42971-09-5
Vinpocetine

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In chloroform	96.1%

: 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

: 42971-09-5
Vinpocetine

: vinpocetine hydrochloride

Conditions

Conditions	Yield
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

Conditions	Yield
With sodium ethanolate In ethanol for 10h; Reflux;	72%

: 42971-09-5
Vinpocetine

: 142892-65-7
(+)-15α-Chloro-vincaminic acid ethyl ester

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With nitric acid In acetic acid for 0.5h; Ambient temperature;	A n/a B n/a C 10%

...Expand

: 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

Conditions	Yield
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;

...Expand

: 42971-09-5
Vinpocetine

A: 57327-92-1
3α-deoxyvincaminic acid ethyl ester

B: 57517-54-1
3α-deoxyepivincaminic acid ethyl ester

Conditions

Conditions	Yield
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

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

...Expand

: 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

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

...Expand

: 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

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

...Expand

: 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

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

...Expand

: 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

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

...Expand

: 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

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

...Expand

: 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

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

...Expand

: 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

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

...Expand

Vinpocetine Chemical Properties

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

Vinpocetine 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.

Vinpocetine 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 NO_x.
Hazard Codes: Xn
Risk Statements: 22
22: Harmful if swallowed
Safety Statements: 36
36: Wear suitable protective clothing
WGK Germany: 3
RTECS: JW4792000

Vinpocetine 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.

Product Name

Vinpocetine

Synthetic route

Vinpocetine Chemical Properties

Vinpocetine Toxicity Data With Reference

Vinpocetine Safety Profile

Vinpocetine Specification

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