• Name

  Catharanthine

• EINECS 219-586-6
• CAS No. 2468-21-5
• Article Data9
• CAS DataBase
• Density 1.27 g/cm³
• Solubility
• Melting Point 138-140 °C
• Formula C₂₁H₂₄N₂O₂
• Boiling Point 491.5 °C at 760 mmHg
• Molecular Weight 336.434
• Flash Point 251.1 °C
• Transport Information
• Appearance off-white to pale beige solid
• Safety
• Risk Codes
• Molecular Structure
• Hazard Symbols
• Synonyms Catharanthine(6CI,7CI,8CI);(+)-3,4-Didehydrocoronaridine;(+)-Catharanthine;Ibogamine-18-carboxylicacid, 3,4-didehydro-, methyl ester, (2a,5b,6a,18b)-;Catharanthine, (+)-;
• PSA 45.33000
• LogP 3.11320

Synthetic route

105729-49-5

(16R)-5-oxo-catharanthine

2468-21-5

catharinthine

Conditions

Conditions	Yield
With sodium tetrahydroborate; boron trifluoride diethyl etherate In tetrahydrofuran for 2h; Ambient temperature;	96.2%

87-51-4

indole-3-acetic acid

2468-21-5

catharinthine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: triethylamine / dimethylformamide / 0.33 h / -10 - -5 °C 2: triethylamine / dimethylformamide / 24 h 3: 29.5 percent / NaBH4, tributyltin chloride / methanol / Irradiation 4: 96.2 percent / NaBH4, boron trifluoride etherate / tetrahydrofuran / 2 h / Ambient temperature View Scheme

125213-31-2

C15H17NO3

2468-21-5

catharinthine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine / dimethylformamide / 24 h 2: 29.5 percent / NaBH4, tributyltin chloride / methanol / Irradiation 3: 96.2 percent / NaBH4, boron trifluoride etherate / tetrahydrofuran / 2 h / Ambient temperature View Scheme

129030-48-4

(-)-2-(1-<2-(indol-3-yl)-1-oxo-ethyl>)-6-ethyl-7-exo-chloro-2-azabicyclo<2.2.2>oct-5-ene-7-endo-carboxylic acid methyl ester

2468-21-5

catharinthine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 29.5 percent / NaBH4, tributyltin chloride / methanol / Irradiation 2: 96.2 percent / NaBH4, boron trifluoride etherate / tetrahydrofuran / 2 h / Ambient temperature View Scheme

stemmadenine acetate

2468-21-5

catharinthine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: T. iboga precondylocarpine acetate synthase 1; FAD / aq. buffer / 2 h / 37 °C / pH 9.5 / Enzymatic reaction 2: NADPH / aq. buffer / 1 h / 37 °C / pH 9.5 / Enzymatic reaction 3: NADPH / aq. buffer / pH 9.5 / Enzymatic reaction View Scheme

C23H27N2O4(1+)

2468-21-5

catharinthine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: NADPH / aq. buffer / 1 h / 37 °C / pH 9.5 / Enzymatic reaction 2: NADPH / aq. buffer / pH 9.5 / Enzymatic reaction View Scheme

dehydrosecodine

2468-21-5

catharinthine

Conditions

Conditions	Yield
With NADPH In aq. buffer pH=9.5; Enzymatic reaction;

2468-21-5

catharinthine

38542-83-5

(+)-dihydrocatharanthine

Conditions

Conditions	Yield
With platinum(IV) oxide; hydrogen In methanol under 760.051 Torr; for 0.0833333h; Inert atmosphere;	93%

2468-21-5

catharinthine

2182-14-1

vindoline

38390-45-3, 56083-20-6, 61246-76-2, 105815-31-4

anhydrovinblastine

Conditions

Conditions	Yield
Stage #1: catharinthine; vindoline With iron(III) chloride hexahydrate at 25℃; Stage #2: With sodium tetrahydroborate at 0℃;	90%
With sodium tetrahydroborate; iron(III) chloride 1.) buffer; Yield given. Multistep reaction;
With hydrogenchloride; iron(III) chloride In 2,2,2-trifluoroethanol; water at 25℃; for 2h; Inert atmosphere;

2468-21-5

catharinthine

79-22-1

methyl chloroformate

60706-87-8

N-(methoxycarbonyl)catharanthine

Conditions

Conditions	Yield
Stage #1: catharinthine With potassium hydride In tetrahydrofuran at 0℃; Stage #2: methyl chloroformate In tetrahydrofuran at 0 - 23℃; for 15h;	90%
Stage #1: catharinthine With potassium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: methyl chloroformate In tetrahydrofuran at 0 - 20℃; for 19h; Inert atmosphere;	86%
Stage #1: catharinthine With potassium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: methyl chloroformate In tetrahydrofuran at 0 - 20℃; for 19h; Inert atmosphere;	86%

7677-24-9

trimethylsilyl cyanide

2468-21-5

catharinthine

136118-90-6

(4S,7R,9S)-methyl 4-cyano-5-ethyl-2,4,7,8,9,10-hexahydro-1H-3,7-methano[1]azacycloundecino[5,4-b]indole-9-carboxylate

Conditions

Conditions	Yield
With 2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione In methanol UV-irradiation;	88%
With eosin B disodium salt In methanol for 2h; Irradiation; Yield given;
With eosin B disodium salt In methanol for 2h; Irradiation; other photooxidants (without O2);
With [Ir(C6H2F2-C5H3NCF3)2(4,4′-di-tert-butyl-2,2′-dipyridyl)]+ In methanol for 0.0333333h; Reagent/catalyst; Inert atmosphere; Irradiation; Flow reactor;	96 %Spectr.

(-)-vindoline

2468-21-5

catharinthine

(+)-anhydrovinblastine

Conditions

Conditions	Yield
Stage #1: (-)-vindoline; catharinthine With iron(III) chloride In hydrogenchloride; 2,2,2-trifluoroethanol; water at 23℃; for 2h; Stage #2: With oxygen; ferric citrate In hydrogenchloride; 2,2,2-trifluoroethanol; water Stage #3: With sodium tetrahydroborate In hydrogenchloride; 2,2,2-trifluoroethanol; water at 0℃; for 0.5h;	87%

2468-21-5

catharinthine

1674-00-6

C19H22N2

Conditions

Conditions	Yield
Stage #1: catharinthine With sodium hydroxide In ethanol at 70℃; for 16h; Stage #2: With hydrogenchloride In ethanol; water at 70℃;	85%
Stage #1: catharinthine With water; sodium hydroxide In ethanol at 70℃; for 16h; Stage #2: With hydrogenchloride In ethanol at 70℃;	85%

2468-21-5

catharinthine

2182-14-1

vindoline

38390-45-3, 56083-20-6, 61246-76-2, 105815-31-4

3',4'-anhydrovinblastine

Conditions

Conditions	Yield
Stage #1: catharinthine With hydrogenchloride In water aq. buffer; Stage #2: vindoline With iron(III) chloride In water at 20℃; for 18h; Stage #3: With sodium tetrahydroborate; ammonia In water at 20℃; for 0.166667h;	80%

4-desacetoxy-6,7-dihydrovindoline

2468-21-5

catharinthine

C44H56N4O6

Conditions

Conditions	Yield
Stage #1: 4-desacetoxy-6,7-dihydrovindoline; catharinthine With iron(III) chloride In hydrogenchloride; 2,2,2-trifluoroethanol; water at 25℃; for 2h; Stage #2: With sodium tetrahydroborate In hydrogenchloride; 2,2,2-trifluoroethanol; water	77%

2468-21-5

catharinthine

C20H24N2O

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 0.166667h;	77%
Stage #1: catharinthine With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 0.166667h; Stage #2: With water; ammonium chloride In tetrahydrofuran	77%

2468-21-5

catharinthine

2182-14-1

vindoline

C46H57N7O8

Conditions

Conditions	Yield
Stage #1: catharinthine; vindoline With hydrogenchloride; iron(III) chloride In 2,2,2-trifluoroethanol; water at 25℃; Stage #2: With sodium tetrahydroborate; cesium azide; ferric oxalate at 0℃; for 0.5h;	75%

2468-21-5

catharinthine

1142118-65-7

isocatharanthine

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol under 225.023 Torr; for 2h;	73%

7677-24-9

trimethylsilyl cyanide

2468-21-5

catharinthine

3β-cyano-7β-hydroxyindolenine catharanthine

Conditions

Conditions	Yield
With oxygen; 5,15,10,20-tetraphenylporphyrin In dichloromethane Irradiation;	72%

2468-21-5

catharinthine

63944-54-7

C20H22N2O2

Conditions

Conditions	Yield
Stage #1: catharinthine With sodium hydroxide In ethanol at 70℃; for 16h; Stage #2: With hydrogenchloride In ethanol; water at 0℃;	70%
Stage #1: catharinthine With water; sodium hydroxide In ethanol at 70℃; for 16h; Stage #2: With hydrogenchloride In ethanol	70%
With potassium hydroxide In ethanol for 8h; Heating;

7677-24-9

trimethylsilyl cyanide

2468-21-5

catharinthine

A

132019-29-5

3-cyanocatharanthine

B

82622-21-7

21-cyanocatharanthine

Conditions

Conditions	Yield
With lithium perchlorate In benzene	A 3% B 68%

...Expand

(-)-vindoline

2468-21-5

catharinthine

A

(+)-anhydrovinblastine

B

(+)-leurosidine

C

(+)-vinblastine

Conditions

Conditions	Yield
Stage #1: (-)-vindoline; catharinthine With iron(III) chloride In hydrogenchloride; 2,2,2-trifluoroethanol; water at 23℃; for 2h; Stage #2: With oxygen; ferric nitrate In hydrogenchloride; 2,2,2-trifluoroethanol; water Stage #3: With sodium tetrahydroborate In hydrogenchloride; 2,2,2-trifluoroethanol; water at 0℃; for 0.5h;	A 63% B 17% C 10%
Stage #1: (-)-vindoline; catharinthine With iron(III) chloride In hydrogenchloride; 2,2,2-trifluoroethanol; water at 23℃; for 2h; Stage #2: With iron(III) sulfate; oxygen In hydrogenchloride; 2,2,2-trifluoroethanol; water Stage #3: With sodium tetrahydroborate In hydrogenchloride; 2,2,2-trifluoroethanol; water at 0℃; for 0.5h;	A 33% B 22% C 39%

...Expand

2468-21-5

catharinthine

90012-96-7

10-iodocatharanthine

Conditions

Conditions	Yield
With N-iodo-succinimide; trifluoroacetic acid In dichloromethane at -40℃; for 2h;	55%

141-52-6

sodium ethanolate

2468-21-5

catharinthine

1257634-10-8

C22H26N2O2

Conditions

Conditions	Yield
In ethanol at 20℃; for 16h;	49%

64-17-5

ethanol

141-52-6

sodium ethanolate

2468-21-5

catharinthine

1257634-10-8

C22H26N2O2

Conditions

Conditions	Yield
at 20℃; for 16h;	49%

...Expand

2468-21-5

catharinthine

1328885-33-1

10-nitrocatharanthine

Conditions

Conditions	Yield
With nitric acid In chloroform; acetic acid at -20℃;	45%

2468-21-5

catharinthine

1257634-12-0

C20H22N2O

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃;	37%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 0.0833333h;	37%

67-56-1

methanol

2468-21-5

catharinthine

132019-27-3

C23H30N2O4

Conditions

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone at -5 - 0℃; for 0.333333h; oxidative fragmentation by DDQ, other reactant, other reagent, other solvent;	35%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone at -5 - 0℃; for 0.333333h;	35%

151-50-8

potassium cyanide

2468-21-5

catharinthine

A

82622-21-7

21-cyanocatharanthine

B

132019-33-1

C22H21N3O2

C

132019-31-9

C22H23N3O2

Conditions

Conditions	Yield
With 18-crown-6 ether; 2,3-dicyano-5,6-dichloro-p-benzoquinone 1) benzene, 25 deg C, 30 min; Yield given. Multistep reaction;	A 30% B n/a C n/a
With 18-crown-6 ether; 2,3-dicyano-5,6-dichloro-p-benzoquinone 1) benzene, 25 deg C, 30 min; Yield given. Multistep reaction. Yields of byproduct given;

...Expand

2468-21-5

catharinthine

A

132019-29-5

3-cyanocatharanthine

B

132019-28-4

2-((Z)-2-Formyl-but-1-enyl)-2,3,6,11-tetrahydro-1H,5H-indolizino[8,7-b]indole-11b-carboxylic acid methyl ester

Conditions

Conditions	Yield
With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran	A 10% B 30%

C23H30N2O3

2468-21-5

catharinthine

C44H54N4O5

Conditions

Conditions	Yield
Stage #1: C23H30N2O3; catharinthine With Trametes versicolor laccase; oxygen at 30℃; for 24h; pH=4.5; aq. acetate buffer; Stage #2: With sodium hydroxide; sodium tetrahydroborate aq. acetate buffer;	21%

151-50-8

potassium cyanide

2468-21-5

catharinthine

A

132019-29-5

3-cyanocatharanthine

B

132019-34-2

C22H21N3O3

Conditions

Conditions	Yield
With 18-crown-6 ether; 2,3-dicyano-5,6-dichloro-p-benzoquinone 1. THF; Multistep reaction;	A 20% B n/a
With 18-crown-6 ether; 2,3-dicyano-5,6-dichloro-p-benzoquinone 1) THF; Yield given. Multistep reaction;

...Expand

7677-24-9

trimethylsilyl cyanide

2468-21-5

catharinthine

300535-95-9

3β-cyanocatharanthine

Conditions

Conditions	Yield
With beta-carotene; oxygen; 5,15,10,20-tetraphenylporphyrin In dichloromethane for 4h; Irradiation;	20%

7677-24-9

trimethylsilyl cyanide

2468-21-5

catharinthine

A

132019-30-8

5-cyanocatharanthine

B

132019-29-5

3-cyanocatharanthine

C

82622-21-7

21-cyanocatharanthine

Conditions

Conditions	Yield
With lithium perchlorate In tetrahydrofuran	A 10% B 18% C 16%

...Expand

2468-21-5

catharinthine

1328885-35-3

10-bromocatharanthine

Conditions

Conditions	Yield
With N-Bromosuccinimide; trifluoroacetic acid In dichloromethane at -40℃; for 2h;	18%

2468-21-5

catharinthine

27773-39-3, 86116-70-3, 106356-44-9

11-methoxytabersonine

C43H50N4O5

Conditions

Conditions	Yield
	4%

Catharanthine Chemical Properties

Catharanthine Uses

Catharanthine Toxicity Data With Reference