Product Name

  • Name

    Vincamine

  • EINECS 216-576-3
  • CAS No. 1617-90-9
  • Article Data43
  • CAS DataBase
  • Density 1.36 g/cm3
  • Solubility
  • Melting Point 232 °C (dec.)(lit.)
  • Formula C21H26N2O3
  • Boiling Point 508.9 °C at 760 mmHg
  • Molecular Weight 354.449
  • Flash Point 261.6 °C
  • Transport Information
  • Appearance white to almost white fine crystalline powder
  • Safety 36
  • Risk Codes 22
  • Molecular Structure Molecular Structure of 1617-90-9 (Vincamine)
  • Hazard Symbols HarmfulXn
  • 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;
  • PSA 54.70000
  • LogP 2.89040

Synthetic route

(+)-15α-Chloro-vincamine
142892-63-5

(+)-15α-Chloro-vincamine

vincamin
1617-90-9

vincamin

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

14-epivincamine

A

vincamin
1617-90-9

vincamin

B

apovincamine
4880-92-6

apovincamine

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

(-)-vincadifformine

vincamin
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%
hydroxy-16 dehydro-1 vincadifformine
66113-74-4

hydroxy-16 dehydro-1 vincadifformine

A

vincamin
1617-90-9

vincamin

B

vinburnine
4880-88-0

vinburnine

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

O-methyl vincamine

A

14-epivincamine
6835-99-0

14-epivincamine

B

vincamin
1617-90-9

vincamin

Conditions
ConditionsYield
With hydrogenchloride In acetone for 72h; Ambient temperature; Yields of byproduct given;A n/a
B 66%
(-)-methyl 1,2,3,4,6,7,12,12bα-octahydroindolo<2,3-a>quinolizine(1β-yl) pyruvate oxime
85588-92-7

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

A

14-epivincamine
6835-99-0

14-epivincamine

B

vincamin
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%
hydroxy-16 dehydro-1 vincadifformine
66113-74-4

hydroxy-16 dehydro-1 vincadifformine

A

14-epivincamine
6835-99-0

14-epivincamine

B

vincamin
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
dichloromethane
75-09-2

dichloromethane

MCPB
94-81-5

MCPB

potassium carbonate
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

vincamin
1617-90-9

vincamin

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

14-epivincamine

A

vincamin
1617-90-9

vincamin

B

vinburnine
4880-88-0

vinburnine

C

apovincamine
4880-92-6

apovincamine

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

(-)-vincadifformine

A

14-epivincamine
6835-99-0

14-epivincamine

B

vincamin
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;
methanol
67-56-1

methanol

(3α,16α)-D-homoeburnamonine-14,15-dione
35226-43-8

(3α,16α)-D-homoeburnamonine-14,15-dione

vincamin
1617-90-9

vincamin

Conditions
ConditionsYield
With potassium tert-butylate at 20℃; for 2h;40%
With potassium tert-butylate for 2h; Ambient temperature;
(-)-vincadifformine hydrochloride

(-)-vincadifformine hydrochloride

A

14-epivincamine
6835-99-0

14-epivincamine

B

vincamin
1617-90-9

vincamin

C

C21H26N2O4
78084-15-8

C21H26N2O4

Conditions
ConditionsYield
With methylene blue In methanol for 4h; Irradiation;A 2 mg
B 10 mg
C 40%
...Expand
diazomethane
186581-53-3, 908094-01-9

diazomethane

(-)-2-(1α-Ethyl-1,2,3,4,6,7,12,12bα-octahydroindolo<2,3-a>quinolizin-1-yl)-2-oxoacetic acid
100945-10-6, 100992-96-9, 120201-19-6

(-)-2-(1α-Ethyl-1,2,3,4,6,7,12,12bα-octahydroindolo<2,3-a>quinolizin-1-yl)-2-oxoacetic acid

A

vincamin
1617-90-9

vincamin

B

(-)-14-oxo-15α-oxirano-eburnane
120090-43-9

(-)-14-oxo-15α-oxirano-eburnane

Conditions
ConditionsYield
In methanol; dichloromethane at 0℃; for 4h; Product distribution; reactions of vincamones and eburnanes;A 38%
B 27%
In methanol; dichloromethane at 0℃; for 4h;A 32%
B 27%
...Expand
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 methyl ester
89396-77-0

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 methyl ester

A

vincamin
1617-90-9

vincamin

B

apovincamine
4880-92-6

apovincamine

Conditions
ConditionsYield
With sulfuric acid; sodium methylate 1.) AcOH, heating, 2 h; 2.) MeOH, rt, 2 h; Yield given. Multistep reaction;A n/a
B 35%
(+)-15,15a-didehydro-15-formamido-D-homoeburnamin-14-one
112965-87-4

(+)-15,15a-didehydro-15-formamido-D-homoeburnamin-14-one

A

14-epivincamine
6835-99-0

14-epivincamine

B

vincamin
1617-90-9

vincamin

Conditions
ConditionsYield
With hydrogenchloride; methanol; acetyl chloride for 4h; Heating; Yield given. Yields of byproduct given;
methyl (1α,12bα,Z)-α-<(2,4-dinitrophenyl)hydrazono>-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-1-propanoate
83289-24-1

methyl (1α,12bα,Z)-α-<(2,4-dinitrophenyl)hydrazono>-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-1-propanoate

(+/-)-16-epi vincamine
18210-81-6

(+/-)-16-epi vincamine

B

vincamin
1617-90-9

vincamin

Conditions
ConditionsYield
With hydrogenchloride; methanol; iron; sodium nitrite 1.) 50 deg C, 16 h, 2.) room temp., 30 min; Yield given. Multistep reaction. Title compound not separated from byproducts;
methyl (1α,12bα,Z)-α-<(2,4-dinitrophenyl)hydrazono>-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-1-propanoate
83289-24-1

methyl (1α,12bα,Z)-α-<(2,4-dinitrophenyl)hydrazono>-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-1-propanoate

A

14-epivincamine
6835-99-0

14-epivincamine

B

vincamin
1617-90-9

vincamin

Conditions
ConditionsYield
With hydrogenchloride; methanol; iron; sodium nitrite 1.) 50 deg C, 16 h, 2.) room temperature, 30 min; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;
With hydrogenchloride; methanol; iron; sodium nitrite 1.) 50 deg C, 16 h, 2.) room temperature, 30 min; Yield given. Multistep reaction. Yields of byproduct given;
14-epivincamine
6835-99-0

14-epivincamine

vincamin
1617-90-9

vincamin

Conditions
ConditionsYield
With ammonium hydroxide In methanol for 4h; Equilibrium constant; Rate constant; Heating;
14-iodo criocerine
74947-45-8

14-iodo criocerine

vincamin
1617-90-9

vincamin

Conditions
ConditionsYield
With sodium cyanoborohydride In acetic acid at 20℃; for 2.5h;8 mg
(1S,12bS,2'S)-1α-ethyl-1β-(2-hydroxy-2-methoxycarbonylethyl)-1,2,3,4,6,7,12,12bα-octahydroindolo<2,3-a>quinolizine
25328-05-6, 25819-96-9, 34786-67-9, 41173-96-0, 55528-20-6, 64395-18-2, 65634-79-9, 65634-80-2, 95782-87-9

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

vincamin
1617-90-9

vincamin

Conditions
ConditionsYield
With sodium methylate 1.) toluene, reflux, 6 h; 2.) MeOH, reflux, 1 h; Yield given. Multistep reaction;
Δ14-vincamine
32790-09-3

Δ14-vincamine

vincamin
1617-90-9

vincamin

Conditions
ConditionsYield
With hydrogen; platinum(IV) oxide In methanol9 mg
Multi-step reaction with 2 steps
1: 49 mg / acetic acid, iodine, potassium iodate / dioxane / 24 h / 20 °C
2: 8 mg / NaBH3CN / acetic acid / 2.5 h / 20 °C
View Scheme
tryptamine
61-54-1

tryptamine

vincamin
1617-90-9

vincamin

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1: 83 percent / tetrahydrofuran / 12 h / 20 °C
2: 83 percent / 1,4-bis(methylamino)pyridine, DCC / CH2Cl2 / 18 h / 20 °C
3: 79 percent / NaH / tetrahydrofuran / 4 h / 20 °C
4: 79 percent / LiBr, H2O / dimethylformamide / 12 h / Heating
5: p-TsOH / toluene / 12 h / Heating
6: 1.) hydroquinone, 2.) 20percent AcOH / 1.) THF, 60 deg C, 2 d,2.) H2O, THF, 40 deg C, 72 h
7: 76 percent / LiOH, 30percent H2O2 / methanol / 5 h / 20 °C
8: 1.) NH2NH2*H2O, 2.) KOH, 3.) conc. HCl / 1.) diethylene glycol, 160 deg C, 1 h, 2.) 220-225 deg C, 4 h, 3.) H2O, 0 deg C, 4.) Et2O, 0 deg C
9: 1.) POCl3, 2.) 1M LiClO4, 3.) H2, 4.) 30percent ammonia / 3.) 10percent Pd/C / 1.) CH3CN, 100 deg C, 4 h, 2.) CH2Cl2, 10 min, 3.) DMF, 1 bar, 5 h
10: 70 percent / sodium bis(trimethylsilyl)amide / toluene; tetrahydrofuran / 2 h / 20 °C
11: 65 percent / tert-butyl nitrite, sodium bis(trimethylsilyl)amide / toluene; tetrahydrofuran / 1.5 h / 50 °C
12: p-TsOH, paraformaldehyde / acetic acid / 5 h / 100 - 105 °C
13: 40 percent / t-BuOK / 2 h / 20 °C
View Scheme
Multi-step reaction with 19 steps
1: 83 percent / tetrahydrofuran / 12 h / 20 °C
2: 83 percent / 1,4-bis(methylamino)pyridine, DCC / CH2Cl2 / 18 h / 20 °C
3: 79 percent / NaH / tetrahydrofuran / 4 h / 20 °C
4: 79 percent / LiBr, H2O / dimethylformamide / 12 h / Heating
5: p-TsOH / toluene / 12 h / Heating
6: 1.) hydroquinone, 2.) 20percent AcOH / 1.) THF, 60 deg C, 2 d,2.) H2O, THF, 40 deg C, 72 h
7: 76 percent / LiOH, 30percent H2O2 / methanol / 5 h / 20 °C
8: 1.) Et3N, isobutyl chloroformate, 2.) NaBH4 / 1.) THF, 0 deg C, 30 min, 2.) CH3OH, 20 deg C, 3 h
9: 68 percent / imidazole / dimethylformamide / 12 h / 20 °C
10: 1.) NaH, imidazole / 1.) THF, 20 deg C, 30 min, 2.) 30 min, 3.) 15 min
11: 85 percent / AIBN, tri-n-butyl hydride / toluene / 2 h / Heating
12: 69 percent / NaH / tetrahydrofuran / 3 h / 20 °C
13: 77 percent / TBAF / tetrahydrofuran / 4 h / 20 °C
14: 1.) pyridinium dichromate, 3.) formic acid / 1.) DMF, 20 deg C, 12 h, 2.) CH2Cl2, Et2O, 3.) 20 deg C, 12 h
15: 1.) POCl3, 2.) 1M LiClO4, 3.) H2, 4.) 30percent ammonia / 3.) 10percent Pd/C / 1.) CH3CN, 100 deg C, 4 h, 2.) CH2Cl2, 10 min, 3.) DMF, 1 bar, 5 h
16: 70 percent / sodium bis(trimethylsilyl)amide / toluene; tetrahydrofuran / 2 h / 20 °C
17: 65 percent / tert-butyl nitrite, sodium bis(trimethylsilyl)amide / toluene; tetrahydrofuran / 1.5 h / 50 °C
18: p-TsOH, paraformaldehyde / acetic acid / 5 h / 100 - 105 °C
19: 40 percent / t-BuOK / 2 h / 20 °C
View Scheme
3-<<2-(1H-indol-3-yl)ethyl>amino>propanoic acid ethyl ester
14487-98-0

3-<<2-(1H-indol-3-yl)ethyl>amino>propanoic acid ethyl ester

vincamin
1617-90-9

vincamin

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1: 83 percent / 1,4-bis(methylamino)pyridine, DCC / CH2Cl2 / 18 h / 20 °C
2: 79 percent / NaH / tetrahydrofuran / 4 h / 20 °C
3: 79 percent / LiBr, H2O / dimethylformamide / 12 h / Heating
4: p-TsOH / toluene / 12 h / Heating
5: 1.) hydroquinone, 2.) 20percent AcOH / 1.) THF, 60 deg C, 2 d,2.) H2O, THF, 40 deg C, 72 h
6: 76 percent / LiOH, 30percent H2O2 / methanol / 5 h / 20 °C
7: 1.) NH2NH2*H2O, 2.) KOH, 3.) conc. HCl / 1.) diethylene glycol, 160 deg C, 1 h, 2.) 220-225 deg C, 4 h, 3.) H2O, 0 deg C, 4.) Et2O, 0 deg C
8: 1.) POCl3, 2.) 1M LiClO4, 3.) H2, 4.) 30percent ammonia / 3.) 10percent Pd/C / 1.) CH3CN, 100 deg C, 4 h, 2.) CH2Cl2, 10 min, 3.) DMF, 1 bar, 5 h
9: 70 percent / sodium bis(trimethylsilyl)amide / toluene; tetrahydrofuran / 2 h / 20 °C
10: 65 percent / tert-butyl nitrite, sodium bis(trimethylsilyl)amide / toluene; tetrahydrofuran / 1.5 h / 50 °C
11: p-TsOH, paraformaldehyde / acetic acid / 5 h / 100 - 105 °C
12: 40 percent / t-BuOK / 2 h / 20 °C
View Scheme
Multi-step reaction with 18 steps
1: 83 percent / 1,4-bis(methylamino)pyridine, DCC / CH2Cl2 / 18 h / 20 °C
2: 79 percent / NaH / tetrahydrofuran / 4 h / 20 °C
3: 79 percent / LiBr, H2O / dimethylformamide / 12 h / Heating
4: p-TsOH / toluene / 12 h / Heating
5: 1.) hydroquinone, 2.) 20percent AcOH / 1.) THF, 60 deg C, 2 d,2.) H2O, THF, 40 deg C, 72 h
6: 76 percent / LiOH, 30percent H2O2 / methanol / 5 h / 20 °C
7: 1.) Et3N, isobutyl chloroformate, 2.) NaBH4 / 1.) THF, 0 deg C, 30 min, 2.) CH3OH, 20 deg C, 3 h
8: 68 percent / imidazole / dimethylformamide / 12 h / 20 °C
9: 1.) NaH, imidazole / 1.) THF, 20 deg C, 30 min, 2.) 30 min, 3.) 15 min
10: 85 percent / AIBN, tri-n-butyl hydride / toluene / 2 h / Heating
11: 69 percent / NaH / tetrahydrofuran / 3 h / 20 °C
12: 77 percent / TBAF / tetrahydrofuran / 4 h / 20 °C
13: 1.) pyridinium dichromate, 3.) formic acid / 1.) DMF, 20 deg C, 12 h, 2.) CH2Cl2, Et2O, 3.) 20 deg C, 12 h
14: 1.) POCl3, 2.) 1M LiClO4, 3.) H2, 4.) 30percent ammonia / 3.) 10percent Pd/C / 1.) CH3CN, 100 deg C, 4 h, 2.) CH2Cl2, 10 min, 3.) DMF, 1 bar, 5 h
15: 70 percent / sodium bis(trimethylsilyl)amide / toluene; tetrahydrofuran / 2 h / 20 °C
16: 65 percent / tert-butyl nitrite, sodium bis(trimethylsilyl)amide / toluene; tetrahydrofuran / 1.5 h / 50 °C
17: p-TsOH, paraformaldehyde / acetic acid / 5 h / 100 - 105 °C
18: 40 percent / t-BuOK / 2 h / 20 °C
View Scheme
(-)-1β-methoxycarbonylethyl-1α-ethyl-1,2,3,4,6,7,12,12bα-octahydroindolo<2,3-a>quinolizine
23944-42-5

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

vincamin
1617-90-9

vincamin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 70 percent / sodium bis(trimethylsilyl)amide / toluene; tetrahydrofuran / 2 h / 20 °C
2: 65 percent / tert-butyl nitrite, sodium bis(trimethylsilyl)amide / toluene; tetrahydrofuran / 1.5 h / 50 °C
3: p-TsOH, paraformaldehyde / acetic acid / 5 h / 100 - 105 °C
4: 40 percent / t-BuOK / 2 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: tert-butyl nitrite, potassium tert-butoxide / toluene; methanol / 3 h / 40 °C
2: 40 percent / acetic acid, sodium disulfite / H2O / 5 h / 92 - 95 °C
View Scheme
Multi-step reaction with 5 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: 60.7 percent / p-TsOH, paraformaldehyde / acetic acid / 5 h / Heating
5: t-BuOK / 2 h / Ambient temperature
View Scheme
Multi-step reaction with 4 steps
1: 60 percent / NaH / toluene / 5 h / Heating
2: tert-butyl nitrite, t-BuOK / toluene / 1 h / Ambient temperature
3: 60.7 percent / p-TsOH, paraformaldehyde / acetic acid / 5 h / Heating
4: t-BuOK / 2 h / Ambient temperature
View Scheme
(+)-(3S,17S)-14-oxo-E-homo-eburnane
35226-41-6

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

vincamin
1617-90-9

vincamin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 65 percent / tert-butyl nitrite, sodium bis(trimethylsilyl)amide / toluene; tetrahydrofuran / 1.5 h / 50 °C
2: p-TsOH, paraformaldehyde / acetic acid / 5 h / 100 - 105 °C
3: 40 percent / t-BuOK / 2 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: tert-butyl nitrite, t-BuOK / toluene / 1 h / Ambient temperature
2: 60.7 percent / p-TsOH, paraformaldehyde / acetic acid / 5 h / Heating
3: t-BuOK / 2 h / Ambient temperature
View Scheme
15a-homo-eburnamenine-14,15-dione 15-oxime
35226-42-7

15a-homo-eburnamenine-14,15-dione 15-oxime

vincamin
1617-90-9

vincamin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: p-TsOH, paraformaldehyde / acetic acid / 5 h / 100 - 105 °C
2: 40 percent / t-BuOK / 2 h / 20 °C
View Scheme
3-ethyl-1-[2-(1H-indol-3-yl)ethyl]-2,4-piperidinedione
190378-04-2

3-ethyl-1-[2-(1H-indol-3-yl)ethyl]-2,4-piperidinedione

vincamin
1617-90-9

vincamin

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: p-TsOH / toluene / 12 h / Heating
2: 1.) hydroquinone, 2.) 20percent AcOH / 1.) THF, 60 deg C, 2 d,2.) H2O, THF, 40 deg C, 72 h
3: 76 percent / LiOH, 30percent H2O2 / methanol / 5 h / 20 °C
4: 1.) NH2NH2*H2O, 2.) KOH, 3.) conc. HCl / 1.) diethylene glycol, 160 deg C, 1 h, 2.) 220-225 deg C, 4 h, 3.) H2O, 0 deg C, 4.) Et2O, 0 deg C
5: 1.) POCl3, 2.) 1M LiClO4, 3.) H2, 4.) 30percent ammonia / 3.) 10percent Pd/C / 1.) CH3CN, 100 deg C, 4 h, 2.) CH2Cl2, 10 min, 3.) DMF, 1 bar, 5 h
6: 70 percent / sodium bis(trimethylsilyl)amide / toluene; tetrahydrofuran / 2 h / 20 °C
7: 65 percent / tert-butyl nitrite, sodium bis(trimethylsilyl)amide / toluene; tetrahydrofuran / 1.5 h / 50 °C
8: p-TsOH, paraformaldehyde / acetic acid / 5 h / 100 - 105 °C
9: 40 percent / t-BuOK / 2 h / 20 °C
View Scheme
Multi-step reaction with 15 steps
1: p-TsOH / toluene / 12 h / Heating
2: 1.) hydroquinone, 2.) 20percent AcOH / 1.) THF, 60 deg C, 2 d,2.) H2O, THF, 40 deg C, 72 h
3: 76 percent / LiOH, 30percent H2O2 / methanol / 5 h / 20 °C
4: 1.) Et3N, isobutyl chloroformate, 2.) NaBH4 / 1.) THF, 0 deg C, 30 min, 2.) CH3OH, 20 deg C, 3 h
5: 68 percent / imidazole / dimethylformamide / 12 h / 20 °C
6: 1.) NaH, imidazole / 1.) THF, 20 deg C, 30 min, 2.) 30 min, 3.) 15 min
7: 85 percent / AIBN, tri-n-butyl hydride / toluene / 2 h / Heating
8: 69 percent / NaH / tetrahydrofuran / 3 h / 20 °C
9: 77 percent / TBAF / tetrahydrofuran / 4 h / 20 °C
10: 1.) pyridinium dichromate, 3.) formic acid / 1.) DMF, 20 deg C, 12 h, 2.) CH2Cl2, Et2O, 3.) 20 deg C, 12 h
11: 1.) POCl3, 2.) 1M LiClO4, 3.) H2, 4.) 30percent ammonia / 3.) 10percent Pd/C / 1.) CH3CN, 100 deg C, 4 h, 2.) CH2Cl2, 10 min, 3.) DMF, 1 bar, 5 h
12: 70 percent / sodium bis(trimethylsilyl)amide / toluene; tetrahydrofuran / 2 h / 20 °C
13: 65 percent / tert-butyl nitrite, sodium bis(trimethylsilyl)amide / toluene; tetrahydrofuran / 1.5 h / 50 °C
14: p-TsOH, paraformaldehyde / acetic acid / 5 h / 100 - 105 °C
15: 40 percent / t-BuOK / 2 h / 20 °C
View Scheme
vincamin
1617-90-9

vincamin

(15S,17S,19S)-15-ethyl-17-(hydroxymethyl)-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18)-tetraen-17-ol
3382-95-4

(15S,17S,19S)-15-ethyl-17-(hydroxymethyl)-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18)-tetraen-17-ol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 66℃; for 1.5h; Inert atmosphere;99%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 66℃; for 1.5h; Inert atmosphere;99%
With sodium tetrahydroborate; boron trifluoride diethyl etherate In tetrahydrofuran at 0℃; for 2.5h;51%
vincamin
1617-90-9

vincamin

2,7-seco 14-epivincamine
59373-44-3

2,7-seco 14-epivincamine

Conditions
ConditionsYield
With 3,7-bis(dimethylamino)phenothiazin-5-ium chloride trihydrate; oxygen In methanol Irradiation;99%
With oxygen; methylene blue for 24h; Irradiation;35%
vincamin
1617-90-9

vincamin

apovincamine
4880-92-6

apovincamine

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene for 2h; Dean-Stark; Reflux; Inert atmosphere;95%
With toluene-4-sulfonic acid In toluene for 2h; Reflux;92%
With toluene-4-sulfonic acid In toluene for 2h; Reflux;92%
ethanol
64-17-5

ethanol

vincamin
1617-90-9

vincamin

14,15-dihydro-14β-hydroxy-(3α,16α)-eburnamenine-14-carboxylic acid ethyl ester
40163-56-2

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

Conditions
ConditionsYield
With titanium(IV) tetraethanolate In various solvent(s) for 8h; Heating;90%
vincamin
1617-90-9

vincamin

(-)-vincamine N-oxide
51442-60-5, 1239866-77-3

(-)-vincamine N-oxide

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In chloroform84.8%
propan-1-ol
71-23-8

propan-1-ol

vincamin
1617-90-9

vincamin

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

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

Conditions
ConditionsYield
With sulfuric acid for 8h; Reflux;81%
With sulfuric acid for 8h; Reflux;81%
methanol
67-56-1

methanol

vincamin
1617-90-9

vincamin

propynoic acid methyl ester
922-67-8

propynoic acid methyl ester

methyl 7-ethyl-14-hydroxy-8-methoxy-3-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]-1,2,3,4,5,6,7,8-octahydro-7,9-ethanoazecino[5,4-b]indole-14-carboxylate

methyl 7-ethyl-14-hydroxy-8-methoxy-3-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]-1,2,3,4,5,6,7,8-octahydro-7,9-ethanoazecino[5,4-b]indole-14-carboxylate

Conditions
ConditionsYield
Reflux;78%
...Expand
ethanol
64-17-5

ethanol

vincamin
1617-90-9

vincamin

propynoic acid methyl ester
922-67-8

propynoic acid methyl ester

A

C27H36N2O6

C27H36N2O6

B

C27H36N2O6

C27H36N2O6

Conditions
ConditionsYield
In tetrahydrofuran at 66℃; for 3.5h; Inert atmosphere;A 78%
B 15%
...Expand
ethanol
64-17-5

ethanol

vincamin
1617-90-9

vincamin

propynoic acid methyl ester
922-67-8

propynoic acid methyl ester

A

methyl (9R,11S,19R)-19-ethoxy-11-ethyl-9-hydroxy-15-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]-8,15-diazatetracyclo[9.6.2.02,7.08,18]nonadeca-1(18),2,4,6-tetraene-9-carboxylate

methyl (9R,11S,19R)-19-ethoxy-11-ethyl-9-hydroxy-15-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]-8,15-diazatetracyclo[9.6.2.02,7.08,18]nonadeca-1(18),2,4,6-tetraene-9-carboxylate

B

methyl (9S,11S,19R)-19-ethoxy-11-ethyl-9-hydroxy-15-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]-8,15-diazatetracyclo[9.6.2.02,7.08,18]nonadeca-1(18),2,4,6-tetraene-9-carboxylate

methyl (9S,11S,19R)-19-ethoxy-11-ethyl-9-hydroxy-15-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]-8,15-diazatetracyclo[9.6.2.02,7.08,18]nonadeca-1(18),2,4,6-tetraene-9-carboxylate

Conditions
ConditionsYield
In chloroform at 62℃; for 4h; Inert atmosphere; diastereoselective reaction;A 15%
B 78%
...Expand
vincamin
1617-90-9

vincamin

(-)-18-iodo-criocerine
74947-45-8

(-)-18-iodo-criocerine

Conditions
ConditionsYield
With iodine; sodium hydrogencarbonate In chloroform for 2h; Ambient temperature;77%
With iodine; sodium hydrogencarbonate In chloroform at 20℃;77%
With iodine; sodium hydrogencarbonate In chloroform; water for 6h; Inert atmosphere;77%
vincamin
1617-90-9

vincamin

n-butyl isocyanide
111-36-4

n-butyl isocyanide

(3S,14S,16S)-eburnane-14-spiro-5'-(3'-butyloxazolidine-2',4'-dione)

(3S,14S,16S)-eburnane-14-spiro-5'-(3'-butyloxazolidine-2',4'-dione)

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 80℃; for 4h;75%
vincamin
1617-90-9

vincamin

isopropyl alcohol
67-63-0

isopropyl alcohol

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

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

Conditions
ConditionsYield
With sulfuric acid for 8h; Reflux;74%

Vincamine Chemical Properties

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

Vincamine 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.

Vincamine 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

Vincamine 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.

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