Reserpine supplier | CasNO.50-55-5

Name
Reserpine
EINECS 200-047-9
CAS No. 50-55-5
Article Data18
CAS DataBase
Density 1.329 g/cm³
Solubility Soluble in water.
Melting Point ~265 °C (dec.)
Formula C₃₃H₄₀N₂O₉
Boiling Point 700.058 °C at 760 mmHg
Molecular Weight 608.689
Flash Point 377.182 °C
Transport Information UN 1219
Appearance off-white crystalline powder
Safety 22-36/37/39-26
Risk Codes 22-67-36-10
Molecular Structure
Hazard Symbols Xn,Xi
Synonyms 3b,20a-Yohimban-16b-carboxylic acid, 18b-hydroxy-11,17a-dimethoxy- methyl ester 3,4,5-trimethoxybenzoate (ester)(8CI);11,17-Dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylic acidmethyl ester;3,4,5-Trimethoxybenzoyl methyl reserpate;Hiposerpil;Loweserp;Methylreserpate 3,4,5-trimethoxybenzoate (ester);Reserpic acid methyl ester 3,4,5-trimethoxybenzoate (ester);
PSA 117.78000
LogP 4.10900

Synthetic route

: ent-11,17β-dimethoxy-16α-methoxycarbonyl-18α-(3,4,5-trimethoxy-benzoyloxy)-15β-yohimb-3-enium; nitrate

: 50-55-5
reserpine

Conditions

Conditions	Yield
With acetic acid; zinc

: ent-11,17β-dimethoxy-16α-methoxycarbonyl-18α-(3,4,5-trimethoxy-benzoyloxy)-15β-yohimb-3-enium; perchlorate

: 50-55-5
reserpine

Conditions

Conditions	Yield
With perchloric acid; zinc

: 482-85-9
Isoreserpin

A: 50-55-5
reserpine

B: 16625-52-8
C33H42N2O9

C: 16625-53-9
2,3-secoreserpine

Conditions

Conditions	Yield
With acetic acid; zinc for 12h; Heating;	A 195 mg B 70 mg C 22 mg

...Expand

: 4521-61-3
3,4,5-Trimethoxybenzoyl chloride

: 2901-66-8
methyl reserpate

: 50-55-5
reserpine

Conditions

Conditions	Yield
With dmap; triethylamine In dichloromethane Ambient temperature; Yield given;
With pyridine at 20℃; for 96h;

(+-)-reserpine: (+-)-reserpine

: 50-55-5
reserpine

Conditions

Conditions	Yield
With camphor-10-sulfonic acid

: 871938-44-2
(1S,2R,3S,4S,7S)-3-(Fluoro-dimethyl-silanyl)-7-hydroxymethyl-5-oxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester

: 50-55-5
reserpine

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: pyridine; 4-dimethylaminopyridine / CH2Cl2 / 10 h / Heating 2: m-chloroperbenzoic acid; Na2PO4 / CH2Cl2 / 15 h / 20 °C 3: Ag2O; CaSO4 / 20 h 4: diisobutylaluminum hydride / diethyl ether; tetrahydrofuran / 0.5 h / -78 °C 5: MgSO4 / acetonitrile / 1 h 6: aq. HCl / tetrahydrofuran / 30 h / 20 °C 7: pyridine / 96 h / 20 °C View Scheme

: 871938-46-4
(1R,5S,6S,7R,9S)-7-Methoxy-3-oxo-9-(toluene-4-sulfonyloxymethyl)-2-oxa-bicyclo[3.2.2]nonane-6-carboxylic acid methyl ester

: 50-55-5
reserpine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: diisobutylaluminum hydride / diethyl ether; tetrahydrofuran / 0.5 h / -78 °C 2: MgSO4 / acetonitrile / 1 h 3: aq. HCl / tetrahydrofuran / 30 h / 20 °C 4: pyridine / 96 h / 20 °C View Scheme

: (1S,2R,3R,5S,6S)-3-Hydroxy-2-methoxy-6-(2-oxo-ethyl)-5-(toluene-4-sulfonyloxymethyl)-cyclohexanecarboxylic acid methyl ester

: 50-55-5
reserpine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: MgSO4 / acetonitrile / 1 h 2: aq. HCl / tetrahydrofuran / 30 h / 20 °C 3: pyridine / 96 h / 20 °C View Scheme

: (1R,5S,6S,7R,9S)-7-Hydroxy-3-oxo-9-(toluene-4-sulfonyloxymethyl)-2-oxa-bicyclo[3.2.2]nonane-6-carboxylic acid methyl ester

: 50-55-5
reserpine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: Ag2O; CaSO4 / 20 h 2: diisobutylaluminum hydride / diethyl ether; tetrahydrofuran / 0.5 h / -78 °C 3: MgSO4 / acetonitrile / 1 h 4: aq. HCl / tetrahydrofuran / 30 h / 20 °C 5: pyridine / 96 h / 20 °C View Scheme

: (1S,2R,3S,4S,7S)-7-Benzyloxymethyl-3-(fluoro-dimethyl-silanyl)-5-oxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester

: 50-55-5
reserpine

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: H2 / Pd/C / ethyl acetate / 30 h / 760 Torr 2: pyridine; 4-dimethylaminopyridine / CH2Cl2 / 10 h / Heating 3: m-chloroperbenzoic acid; Na2PO4 / CH2Cl2 / 15 h / 20 °C 4: Ag2O; CaSO4 / 20 h 5: diisobutylaluminum hydride / diethyl ether; tetrahydrofuran / 0.5 h / -78 °C 6: MgSO4 / acetonitrile / 1 h 7: aq. HCl / tetrahydrofuran / 30 h / 20 °C 8: pyridine / 96 h / 20 °C View Scheme

Yield

Multi-step reaction with 8 steps
1: H2 / Pd/C / ethyl acetate / 30 h / 760 Torr
2: pyridine; 4-dimethylaminopyridine / CH2Cl2 / 10 h / Heating
3: m-chloroperbenzoic acid; Na2PO4 / CH2Cl2 / 15 h / 20 °C
4: Ag2O; CaSO4 / 20 h
5: diisobutylaluminum hydride / diethyl ether; tetrahydrofuran / 0.5 h / -78 °C
6: MgSO4 / acetonitrile / 1 h
7: aq. HCl / tetrahydrofuran / 30 h / 20 °C
8: pyridine / 96 h / 20 °C
View Scheme

: 871938-43-1
(1S,2R,3S,4S,7S)-7-Benzyloxymethyl-3-(furan-2-yl-dimethyl-silanyl)-5-oxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester

: 50-55-5
reserpine

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: tetrabutylammonium fluoride / tetrahydrofuran / 0.03 h / 20 °C 2: H2 / Pd/C / ethyl acetate / 30 h / 760 Torr 3: pyridine; 4-dimethylaminopyridine / CH2Cl2 / 10 h / Heating 4: m-chloroperbenzoic acid; Na2PO4 / CH2Cl2 / 15 h / 20 °C 5: Ag2O; CaSO4 / 20 h 6: diisobutylaluminum hydride / diethyl ether; tetrahydrofuran / 0.5 h / -78 °C 7: MgSO4 / acetonitrile / 1 h 8: aq. HCl / tetrahydrofuran / 30 h / 20 °C 9: pyridine / 96 h / 20 °C View Scheme

Yield

Multi-step reaction with 9 steps
1: tetrabutylammonium fluoride / tetrahydrofuran / 0.03 h / 20 °C
2: H2 / Pd/C / ethyl acetate / 30 h / 760 Torr
3: pyridine; 4-dimethylaminopyridine / CH2Cl2 / 10 h / Heating
4: m-chloroperbenzoic acid; Na2PO4 / CH2Cl2 / 15 h / 20 °C
5: Ag2O; CaSO4 / 20 h
6: diisobutylaluminum hydride / diethyl ether; tetrahydrofuran / 0.5 h / -78 °C
7: MgSO4 / acetonitrile / 1 h
8: aq. HCl / tetrahydrofuran / 30 h / 20 °C
9: pyridine / 96 h / 20 °C
View Scheme

: 871938-45-3
(1S,2R,3S,4S,7S)-3-(Fluoro-dimethyl-silanyl)-5-oxo-7-(toluene-4-sulfonyloxymethyl)-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester

: 50-55-5
reserpine

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: m-chloroperbenzoic acid; Na2PO4 / CH2Cl2 / 15 h / 20 °C 2: Ag2O; CaSO4 / 20 h 3: diisobutylaluminum hydride / diethyl ether; tetrahydrofuran / 0.5 h / -78 °C 4: MgSO4 / acetonitrile / 1 h 5: aq. HCl / tetrahydrofuran / 30 h / 20 °C 6: pyridine / 96 h / 20 °C View Scheme

: (3R,4aS,5S,6R,7R,8aS)-3-Cyano-7-hydroxy-6-methoxy-2-[2-(6-methoxy-1H-indol-3-yl)-ethyl]-decahydro-isoquinoline-5-carboxylic acid methyl ester

: 50-55-5
reserpine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. HCl / tetrahydrofuran / 30 h / 20 °C 2: pyridine / 96 h / 20 °C View Scheme

: 185810-96-2
(3aS,4S,6R,7S,7aS)-6-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-7-methoxy-hexahydro-benzofuran-4,7a-dicarboxylic acid dimethyl ester

: 50-55-5
reserpine

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: pivalic acid / benzene / Heating 2: pivalic acid / toluene / Heating 3: 100 percent / 2,6-lutidine / CH2Cl2 / 4 h / Ambient temperature 4: 1.) BH3*THF, 2.) ethylene glycol / 1.) THF, room temperature, 6 h, 2.) THF, HMPA, overnight 5: aq. HF / acetonitrile / 0.5 h / Ambient temperature 6: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C 7: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h 8: aq. HF / acetonitrile / 3 h / Ambient temperature 9: Et3N, DMAP / CH2Cl2 / Ambient temperature View Scheme
Multi-step reaction with 8 steps 1: 56 mg / pivalic acid / toluene / 0.83 h / Heating 2: 100 percent / 2,6-lutidine / CH2Cl2 / 4 h / Ambient temperature 3: 1.) BH3*THF, 2.) ethylene glycol / 1.) THF, room temperature, 6 h, 2.) THF, HMPA, overnight 4: aq. HF / acetonitrile / 0.5 h / Ambient temperature 5: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C 6: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h 7: aq. HF / acetonitrile / 3 h / Ambient temperature 8: Et3N, DMAP / CH2Cl2 / Ambient temperature View Scheme

Yield

Multi-step reaction with 9 steps
1: pivalic acid / benzene / Heating
2: pivalic acid / toluene / Heating
3: 100 percent / 2,6-lutidine / CH2Cl2 / 4 h / Ambient temperature
4: 1.) BH3*THF, 2.) ethylene glycol / 1.) THF, room temperature, 6 h, 2.) THF, HMPA, overnight
5: aq. HF / acetonitrile / 0.5 h / Ambient temperature
6: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C
7: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h
8: aq. HF / acetonitrile / 3 h / Ambient temperature
9: Et3N, DMAP / CH2Cl2 / Ambient temperature
View Scheme

Multi-step reaction with 8 steps
1: 56 mg / pivalic acid / toluene / 0.83 h / Heating
2: 100 percent / 2,6-lutidine / CH2Cl2 / 4 h / Ambient temperature
3: 1.) BH3*THF, 2.) ethylene glycol / 1.) THF, room temperature, 6 h, 2.) THF, HMPA, overnight
4: aq. HF / acetonitrile / 0.5 h / Ambient temperature
5: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C
6: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h
7: aq. HF / acetonitrile / 3 h / Ambient temperature
8: Et3N, DMAP / CH2Cl2 / Ambient temperature
View Scheme

: 185810-94-0
(3aS,4S,6R,7S,7aS)-6-(tert-Butyl-dimethyl-silanyloxy)-7-methoxy-2-oxo-hexahydro-benzofuran-4,7a-dicarboxylic acid dimethyl ester

: 50-55-5
reserpine

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1: 98 percent / disiamylborane / tetrahydrofuran / 4 h / Ambient temperature 2: pivalic acid / benzene / Heating 3: pivalic acid / toluene / Heating 4: 100 percent / 2,6-lutidine / CH2Cl2 / 4 h / Ambient temperature 5: 1.) BH3*THF, 2.) ethylene glycol / 1.) THF, room temperature, 6 h, 2.) THF, HMPA, overnight 6: aq. HF / acetonitrile / 0.5 h / Ambient temperature 7: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C 8: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h 9: aq. HF / acetonitrile / 3 h / Ambient temperature 10: Et3N, DMAP / CH2Cl2 / Ambient temperature View Scheme
Multi-step reaction with 9 steps 1: 98 percent / disiamylborane / tetrahydrofuran / 4 h / Ambient temperature 2: 56 mg / pivalic acid / toluene / 0.83 h / Heating 3: 100 percent / 2,6-lutidine / CH2Cl2 / 4 h / Ambient temperature 4: 1.) BH3*THF, 2.) ethylene glycol / 1.) THF, room temperature, 6 h, 2.) THF, HMPA, overnight 5: aq. HF / acetonitrile / 0.5 h / Ambient temperature 6: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C 7: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h 8: aq. HF / acetonitrile / 3 h / Ambient temperature 9: Et3N, DMAP / CH2Cl2 / Ambient temperature View Scheme

Yield

Multi-step reaction with 10 steps
1: 98 percent / disiamylborane / tetrahydrofuran / 4 h / Ambient temperature
2: pivalic acid / benzene / Heating
3: pivalic acid / toluene / Heating
4: 100 percent / 2,6-lutidine / CH2Cl2 / 4 h / Ambient temperature
5: 1.) BH3*THF, 2.) ethylene glycol / 1.) THF, room temperature, 6 h, 2.) THF, HMPA, overnight
6: aq. HF / acetonitrile / 0.5 h / Ambient temperature
7: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C
8: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h
9: aq. HF / acetonitrile / 3 h / Ambient temperature
10: Et3N, DMAP / CH2Cl2 / Ambient temperature
View Scheme

Multi-step reaction with 9 steps
1: 98 percent / disiamylborane / tetrahydrofuran / 4 h / Ambient temperature
2: 56 mg / pivalic acid / toluene / 0.83 h / Heating
3: 100 percent / 2,6-lutidine / CH2Cl2 / 4 h / Ambient temperature
4: 1.) BH3*THF, 2.) ethylene glycol / 1.) THF, room temperature, 6 h, 2.) THF, HMPA, overnight
5: aq. HF / acetonitrile / 0.5 h / Ambient temperature
6: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C
7: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h
8: aq. HF / acetonitrile / 3 h / Ambient temperature
9: Et3N, DMAP / CH2Cl2 / Ambient temperature
View Scheme

: 1055030-50-6
(3aS,4S,6R,7S,7aS)-6-(tert-Butyl-dimethyl-silanyloxy)-7-methoxy-2-oxo-hexahydro-benzofuran-4,7a-dicarboxylic acid 4-methyl ester

: 50-55-5
reserpine

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1: diethyl ether / 0.08 h / 0 °C 2: 98 percent / disiamylborane / tetrahydrofuran / 4 h / Ambient temperature 3: pivalic acid / benzene / Heating 4: pivalic acid / toluene / Heating 5: 100 percent / 2,6-lutidine / CH2Cl2 / 4 h / Ambient temperature 6: 1.) BH3*THF, 2.) ethylene glycol / 1.) THF, room temperature, 6 h, 2.) THF, HMPA, overnight 7: aq. HF / acetonitrile / 0.5 h / Ambient temperature 8: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C 9: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h 10: aq. HF / acetonitrile / 3 h / Ambient temperature 11: Et3N, DMAP / CH2Cl2 / Ambient temperature View Scheme
Multi-step reaction with 10 steps 1: diethyl ether / 0.08 h / 0 °C 2: 98 percent / disiamylborane / tetrahydrofuran / 4 h / Ambient temperature 3: 56 mg / pivalic acid / toluene / 0.83 h / Heating 4: 100 percent / 2,6-lutidine / CH2Cl2 / 4 h / Ambient temperature 5: 1.) BH3*THF, 2.) ethylene glycol / 1.) THF, room temperature, 6 h, 2.) THF, HMPA, overnight 6: aq. HF / acetonitrile / 0.5 h / Ambient temperature 7: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C 8: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h 9: aq. HF / acetonitrile / 3 h / Ambient temperature 10: Et3N, DMAP / CH2Cl2 / Ambient temperature View Scheme

Yield

Multi-step reaction with 11 steps
1: diethyl ether / 0.08 h / 0 °C
2: 98 percent / disiamylborane / tetrahydrofuran / 4 h / Ambient temperature
3: pivalic acid / benzene / Heating
4: pivalic acid / toluene / Heating
5: 100 percent / 2,6-lutidine / CH2Cl2 / 4 h / Ambient temperature
6: 1.) BH3*THF, 2.) ethylene glycol / 1.) THF, room temperature, 6 h, 2.) THF, HMPA, overnight
7: aq. HF / acetonitrile / 0.5 h / Ambient temperature
8: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C
9: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h
10: aq. HF / acetonitrile / 3 h / Ambient temperature
11: Et3N, DMAP / CH2Cl2 / Ambient temperature
View Scheme

Multi-step reaction with 10 steps
1: diethyl ether / 0.08 h / 0 °C
2: 98 percent / disiamylborane / tetrahydrofuran / 4 h / Ambient temperature
3: 56 mg / pivalic acid / toluene / 0.83 h / Heating
4: 100 percent / 2,6-lutidine / CH2Cl2 / 4 h / Ambient temperature
5: 1.) BH3*THF, 2.) ethylene glycol / 1.) THF, room temperature, 6 h, 2.) THF, HMPA, overnight
6: aq. HF / acetonitrile / 0.5 h / Ambient temperature
7: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C
8: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h
9: aq. HF / acetonitrile / 3 h / Ambient temperature
10: Et3N, DMAP / CH2Cl2 / Ambient temperature
View Scheme

: 185811-08-9
(1S,2R,3R,4aS,13bR,14aS)-3-(tert-Butyl-dimethyl-silanyloxy)-2,11-dimethoxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester

: 50-55-5
reserpine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. HF / acetonitrile / 3 h / Ambient temperature 2: Et3N, DMAP / CH2Cl2 / Ambient temperature View Scheme

: 1053614-44-0
(1S,2S,3R,4aS,13bR,14aS)-3-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-2,11-dimethoxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester

: 50-55-5
reserpine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C 2: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h 3: aq. HF / acetonitrile / 3 h / Ambient temperature 4: Et3N, DMAP / CH2Cl2 / Ambient temperature View Scheme

: (1S,2S,3S,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-6-methoxy-2-{2-[(Z)-2-(6-methoxy-1H-indol-3-yl)-ethylimino]-ethyl}-cyclohexane-1,3-dicarboxylic acid dimethyl ester

: 50-55-5
reserpine

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: pivalic acid / toluene / Heating 2: 100 percent / 2,6-lutidine / CH2Cl2 / 4 h / Ambient temperature 3: 1.) BH3*THF, 2.) ethylene glycol / 1.) THF, room temperature, 6 h, 2.) THF, HMPA, overnight 4: aq. HF / acetonitrile / 0.5 h / Ambient temperature 5: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C 6: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h 7: aq. HF / acetonitrile / 3 h / Ambient temperature 8: Et3N, DMAP / CH2Cl2 / Ambient temperature View Scheme

Yield

Multi-step reaction with 8 steps
1: pivalic acid / toluene / Heating
2: 100 percent / 2,6-lutidine / CH2Cl2 / 4 h / Ambient temperature
3: 1.) BH3*THF, 2.) ethylene glycol / 1.) THF, room temperature, 6 h, 2.) THF, HMPA, overnight
4: aq. HF / acetonitrile / 0.5 h / Ambient temperature
5: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C
6: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h
7: aq. HF / acetonitrile / 3 h / Ambient temperature
8: Et3N, DMAP / CH2Cl2 / Ambient temperature
View Scheme

: 185811-05-6
(1S,2S,3R,4aS,13bR,14aS)-3-(tert-Butyl-dimethyl-silanyloxy)-2,11-dimethoxy-1-trimethylsilanyloxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester

: 50-55-5
reserpine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: aq. HF / acetonitrile / 0.5 h / Ambient temperature 2: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C 3: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h 4: aq. HF / acetonitrile / 3 h / Ambient temperature 5: Et3N, DMAP / CH2Cl2 / Ambient temperature View Scheme

: 1054654-18-0
(1S,2S,3R,4aS,13bR,14aS)-1,3-Bis-(tert-butyl-dimethyl-silanyloxy)-2,11-dimethoxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester

: 50-55-5
reserpine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h 2: aq. HF / acetonitrile / 3 h / Ambient temperature 3: Et3N, DMAP / CH2Cl2 / Ambient temperature View Scheme

: 185811-02-3
(1S,2S,3R,4aS,13bR,14aS)-3-(tert-Butyl-dimethyl-silanyloxy)-2,11-dimethoxy-5-oxo-1-trimethylsilanyloxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester

: 50-55-5
reserpine

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 1.) BH3*THF, 2.) ethylene glycol / 1.) THF, room temperature, 6 h, 2.) THF, HMPA, overnight 2: aq. HF / acetonitrile / 0.5 h / Ambient temperature 3: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C 4: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h 5: aq. HF / acetonitrile / 3 h / Ambient temperature 6: Et3N, DMAP / CH2Cl2 / Ambient temperature View Scheme

Yield

Multi-step reaction with 6 steps
1: 1.) BH3*THF, 2.) ethylene glycol / 1.) THF, room temperature, 6 h, 2.) THF, HMPA, overnight
2: aq. HF / acetonitrile / 0.5 h / Ambient temperature
3: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C
4: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h
5: aq. HF / acetonitrile / 3 h / Ambient temperature
6: Et3N, DMAP / CH2Cl2 / Ambient temperature
View Scheme

: 185810-98-4
(1S,2S,3R,4aS,13bR,14aS)-3-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-2,11-dimethoxy-5-oxo-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester

: 50-55-5
reserpine

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 100 percent / 2,6-lutidine / CH2Cl2 / 4 h / Ambient temperature 2: 1.) BH3*THF, 2.) ethylene glycol / 1.) THF, room temperature, 6 h, 2.) THF, HMPA, overnight 3: aq. HF / acetonitrile / 0.5 h / Ambient temperature 4: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C 5: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h 6: aq. HF / acetonitrile / 3 h / Ambient temperature 7: Et3N, DMAP / CH2Cl2 / Ambient temperature View Scheme

Yield

Multi-step reaction with 7 steps
1: 100 percent / 2,6-lutidine / CH2Cl2 / 4 h / Ambient temperature
2: 1.) BH3*THF, 2.) ethylene glycol / 1.) THF, room temperature, 6 h, 2.) THF, HMPA, overnight
3: aq. HF / acetonitrile / 0.5 h / Ambient temperature
4: 2,6-lutidine / CH2Cl2 / 0.17 h / 0 °C
5: ethylene glycol, SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 8 h
6: aq. HF / acetonitrile / 3 h / Ambient temperature
7: Et3N, DMAP / CH2Cl2 / Ambient temperature
View Scheme

: 50-55-5
reserpine

: 2901-66-8
methyl reserpate

Conditions

Conditions	Yield
With methanol; sodium methylate for 4h; Reflux;	97%
With potassium hydroxide Hydrolysis;
With sodium methylate Hydrolysis;
Stage #1: reserpine With methanol; sodium methylate for 1h; Heating / reflux; Stage #2: With hydrogenchloride; methanol; water pH=1; Stage #3: With ammonia; water Product distribution / selectivity;
With sodium methylate In methanol for 1h; Heating / reflux;

: 50-55-5
reserpine

: 74-88-4
methyl iodide

: 60634-65-3
N-methylreserpine

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide for 2h;	83%

: 50-55-5
reserpine

: 6811-42-3
(1S,4R,5aS,14bR,15aS,16R)-12,16-dimethoxy-4,5,5a,6,8,9,14,14b,15,15a-decahydro-1,4-methanoindolo[2,3-a]-oxepino[4,5-g]quinolizin-2(1H)-one

Conditions

Conditions	Yield
With aluminum isopropoxide In xylene for 6h; Heating;	81%
With aluminum isopropoxide In xylene for 6h; Product distribution / selectivity; Heating / reflux;	81%
With aluminum isopropoxide; xylene

: 50-55-5
reserpine

: reserpic acid lactone

Conditions

Conditions	Yield
With aluminum isopropoxide In xylene for 6h; Product distribution / selectivity; Heating / reflux;	81%

: 50-55-5
reserpine

: 513-42-8
3-hydroxy-2-methyl-1-propene

: (1S,2R,3R,4aS,13bR,14aS)-methyl-2,11-dimethoxy-13-(2-methylallyl)-3-((3,4,5-trimethoxybenzoyl)oxy)-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydroindolo[2',3':3,4]-pyrido[1,2-b]isoquinoline-1-carboxylate

Conditions

Conditions	Yield
With titanium(IV) isopropylate; 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 80℃; Inert atmosphere; Schlenk technique;	66%

: 50-55-5
reserpine

: 106-96-7
propargyl bromide

A: 1227009-31-5
C36H42N2O9

B: 1227009-32-6
reserpine

Conditions

Conditions	Yield
Stage #1: reserpine With sodium hydride In N,N-dimethyl-formamide; mineral oil at -20℃; for 0.25h; Stage #2: propargyl bromide In N,N-dimethyl-formamide; toluene; mineral oil at -20℃; for 1h;	A 30% B 63%

...Expand

: 50-55-5
reserpine

: 127518-55-2
dioxyreserpine

Conditions

Conditions	Yield
With oxygen; 1,5-Dichloroanthraquinone In acetonitrile at 20℃; for 2.5h; Sealed tube; Inert atmosphere; Irradiation;	63%

: 50-55-5
reserpine

: 474-48-6
11,17-dimethoxy-4-oxy-18-(3,4,5-trimethoxy-benzoyloxy)-yohimbane-16-carboxylic acid methyl ester

Conditions

Conditions	Yield
With dihydrogen peroxide In acetone at 50℃; for 24h;	60%
With monoperoxyphthalic acid
With Perbenzoic acid

: 50-55-5
reserpine

: 35466-83-2
allyl methyl carbonate

: C36H44N2O9

Conditions

Conditions	Yield
Stage #1: allyl methyl carbonate With tris(dibenzylideneacetone)dipalladium (0); trifuran-2-yl-phosphane In dichloromethane at 20℃; Inert atmosphere; Stage #2: reserpine In dichloromethane at 20℃; Inert atmosphere;	60%

: 50-55-5
reserpine

: 106-31-0
butanoic acid anhydride

A: 10-butyryl-16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

B: 12-butyryl-16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

Conditions

Conditions	Yield
With aluminium trichloride at 20℃; Friedel-Crafts acylation;	A 56% B 17%

...Expand

: 50-55-5
reserpine

: 79-03-8
propionyl chloride

A: 16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-12-propionyl-3β,20α-yohimban

B: 16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-10-propionyl-3β,20α-yohimban

C: 16β-carbomethoxy-18β-(5'-hydroxy-4',6'-dimethoxybenzoyloxy)-11,17α-dimethoxy-10-propionyl-3β,20α-yohimban

Conditions

Conditions	Yield
With aluminium trichloride at 20℃; Friedel-Crafts acylation;	A 16% B 56% C 3%

...Expand

: 50-55-5
reserpine

: (1S,2R,3R,4aS,8aS,13aR,13bR,14aS)-2,11-Dimethoxy-3-(3,4,5-trimethoxy-benzoyloxy)-1,2,3,4,4a,5,7,8,8a,13,13a,13b,14,14a-tetradecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester

Conditions

Conditions	Yield
With sodium cyanoborohydride In trifluoroacetic acid for 1h; Ambient temperature;	55%

: 50-55-5
reserpine

: 142-61-0
Hexanoyl chloride

A: 16β-carbomethoxy-10-hexanoyl-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

B: 16β-carbomethoxy-12-hexanoyl-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

Conditions

Conditions	Yield
With aluminium trichloride at 20℃; Friedel-Crafts acylation;	A 55% B 16%

...Expand

: 50-55-5
reserpine

: 2528-61-2
Heptanoic acid chloride

A: 16β-carbomethoxy-10-heptanoyl-18β-(5'-hydroxy-4',6'-dimethoxybenzoyloxy)-11,17α-dimethoxy-3β,20α-yohimban

B: 16β-carbomethoxy-10-heptanoyl-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

C: 16β-carbomethoxy-12-heptanoyl-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

Conditions

Conditions	Yield
With aluminium trichloride at 20℃; Friedel-Crafts acylation;	A 2% B 55% C 18%

...Expand

: 50-55-5
reserpine

: 108-24-7
acetic anhydride

A: 10-acetyl-16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

B: 12-acetyl-16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

C: 10,12-diacetyl-16β-carbomethoxy-11,17α-dimethoxy-18β-(5'-hydroxy-4',6'-dimethoxybenzoyloxy)-3β,20α-yohimban

Conditions

Conditions	Yield
With aluminium trichloride at 20℃; Friedel-Crafts acylation;	A 54% B 14% C 2%

...Expand

: 50-55-5
reserpine

: 638-29-9
n-valeryl chloride

A: 16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-10-valeryl-3β,20α-yohimban

B: 16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-12-valeryl-3β,20α-yohimban

C: 16β-carbomethoxy-18β-(5'-hydroxy-4',6'-dimethoxybenzoyloxy)-11,17α-dimethoxy-10-valeryl-3β,20α-yohimban

Conditions

Conditions	Yield
With aluminium trichloride at 20℃; Friedel-Crafts acylation;	A 51% B 18% C 4%

...Expand

: 50-55-5
reserpine

: 111-64-8
n-octanoic acid chloride

A: 12-capryloyl-16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

B: 10-capryloyl-16β-carbomethoxy-11,17α-dimethoxy-18β-(4',5',6'-trimethoxybenzoyloxy)-3β,20α-yohimban

C: 10-capryloyl-16β-carbomethoxy-18β-(5'-hydroxy-4',6'-dimethoxybenzoyloxy)-11,17α-dimethoxy-3β,20α-yohimban

Conditions

Conditions	Yield
With aluminium trichloride at 20℃; Friedel-Crafts acylation;	A 18% B 50% C 2%

...Expand

: 50-55-5
reserpine

: 21432-74-6
methyl (1R,15S,17R,18R,19S,20S)-17-[(4-hydroxy-3,5-dimethoxyphenyl)carbonyloxy]-6,18-dimethoxy-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8-tetraene-19-carboxylate

Conditions

Conditions	Yield
Stage #1: reserpine With aluminum (III) chloride In dichloromethane for 2h; Stage #2: With hydrogenchloride In dichloromethane; water for 0.0833333h; Product distribution / selectivity;	47.1%
Stage #1: reserpine With aluminum (III) chloride In acetonitrile at 25℃; for 2h; Stage #2: With hydrogenchloride In water; acetonitrile for 0.0833333h; Product distribution / selectivity;	22.4%
Stage #1: reserpine With aluminum tri-bromide In dichloromethane at 25℃; for 2h; Stage #2: With hydrogenchloride In dichloromethane; water for 0.0833333h; Product distribution / selectivity;	22.4%

: 50-55-5
reserpine

A: hydroxyindolenine

B: 127518-54-1
7-hydroperoxy-7H-reserpine

C: 127518-55-2
dioxyreserpine

Conditions

Conditions	Yield
With oxygen In acetonitrile for 2.5h; Irradiation; Inert atmosphere;	A n/a B n/a C 46%

...Expand

: 50-55-5
reserpine

: 50-00-0
formaldehyd

: (1S,2R,3R,4aS,8aS,13aR,13bR,14aS)-2,11-Dimethoxy-10,13-dimethyl-3-(3,4,5-trimethoxy-benzoyloxy)-1,2,3,4,4a,5,7,8,8a,13,13a,13b,14,14a-tetradecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester

Conditions

Conditions	Yield
With sodium cyanoborohydride; trifluoroacetic acid In water at -5 - 20℃; for 0.75h; Mechanism; other indole alkaloids like tetraphylline, epireserpine, and reserpine; also AcOH as reagent; var. temp. and time;	44.5%
With sodium cyanoborohydride; trifluoroacetic acid In water a) -5 deg C, 15 min, b) RT, 30 min;	44.5%

: 50-55-5
reserpine

: 50-00-0
formaldehyd

: 7-2H-1,10-dimethyl-2,7-dihydroreserpine

Conditions

Conditions	Yield
With trifluoroacetic acid-d1; sodium cyanoborohydride In water at 0℃; for 0.5h;	42%

: 50-55-5
reserpine

: 24424-99-5
di-tert-butyl dicarbonate

: 913379-66-5
N-(tert-butyloxycarbonyl)reserpine

Conditions

Conditions	Yield
With dmap In acetonitrile at 20℃; for 12h;	38%

: 50-55-5
reserpine

A: 482-85-9
Isoreserpin

B: 257622-17-6
(6aS,8R,9R,10S,10aS,11aS)-2-(2-Amino-4-methoxy-phenyl)-9-methoxy-8-(3,4,5-trimethoxy-benzoyloxy)-3,6,6a,7,8,9,10,10a,11,11a-decahydro-4H-pyrido[1,2-b]isoquinoline-10-carboxylic acid methyl ester

C: 2,7-dihydroisoreserpine

Conditions

Conditions	Yield
With trifluoroacetic acid; zinc for 4h; Reduction; Heating;	A 10% B 15% C 35%

...Expand

: 50-55-5
reserpine

: 98-54-4
para-tert-butylphenol

: N-(hepta-3,5-diyn-1-yl)-N-(penta-1,3-diyn-1-yl)methanesulfonamide

: C56H67N3O12S

Conditions

Conditions	Yield
In benzene at 85℃; for 16h; Diels-Alder Cycloaddition; Sealed tube; regioselective reaction;	35%

...Expand

: 50-55-5
reserpine

A: 127518-54-1
7-hydroperoxy-7H-reserpine

B: 127518-55-2
dioxyreserpine

Conditions

Conditions	Yield
With oxygen In chloroform for 360h; Mechanism; Ambient temperature; Irradiation; also with deuterated substrate;	A 5.8% B 28.1%
With oxygen In chloroform for 15h; Ambient temperature; Irradiation;	A 5.8% B 28.1%
With oxygen In chloroform for 2.5h; Inert atmosphere; Irradiation;

: 50-55-5
reserpine

: hydroxyindolenine

Conditions

Conditions	Yield
Stage #1: reserpine With lead acetate In dichloromethane at 0℃; for 1.33333h; Inert atmosphere; Irradiation; Stage #2: With sodium methylate In methanol at 0℃; for 2.5h; Inert atmosphere; Irradiation;	9%

: 50-55-5
reserpine

: 482-85-9
Isoreserpin

Conditions

Conditions	Yield
With acetic anhydride
With acetic acid; trichloroacetic acid
With trifluoroacetic acid epimerization; Heating;
With hydrogenchloride In methanol at 68℃; for 12h; Mechanism;	280 mg
With hydrogenchloride In methanol for 72h; Heating;	18 g

: 50-55-5
reserpine

: 11,17-dimethoxy-18-(3,4,5-trimethoxy-benzoyloxy)-yohimb-2-ene-16-carboxylic acid methyl ester

Conditions

Conditions	Yield
With mercury(II) diacetate
With sodium nitrite

: 50-55-5
reserpine

: 119720-94-4
ent-11,17β-dimethoxy-16α-methoxycarbonyl-18α-(3,4,5-trimethoxy-benzoyloxy)-15β-yohimba-3,5-dienium; chloride

Conditions

Conditions	Yield
With lead(IV) acetate; acetic acid Behandeln des Reaktionsprodukts mit wss.HCl;

: 50-55-5
reserpine

: ent-11,17β-dimethoxy-16α-methoxycarbonyl-18α-(3,4,5-trimethoxy-benzoyloxy)-15β-yohimba-3,5-dienium; perchlorate

Conditions

Conditions	Yield
With methanol; palladium; maleic acid Behandeln der Reaktionsloesung mit HClO4;

Reserpine History

Reserpine(50-55-5) was isolated in 1952 from the dried root of Rauwolfia serpentina,it has been discontinued in the UK for some years due to its numerous interactions and side effects,it was also highly influential in promoting the thought of a biogenic-amine hypothesis of depression.

Reserpine Consensus Reports

NTP 10th Report on Carcinogens. IARC Cancer Review: Group 3 IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 330.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 10 ,1976,p. 217.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human Limited Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 24 ,1980,p. 211.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Limited Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 24 ,1980,p. 211.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . NCI Carcinogenesis Bioassay (feed); Clear Evidence: mouse, rat NCITR* National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-193 ,1980. . Reported in EPA TSCA Inventory.

Reserpine Specification

The Reserpine, with the CAS registry number 50-55-5, is also known as Methyl 18b-Hydroxy-11,17a-dimethoxy-3b,20a-yohimban-16b-carboxylate 3,4,5-Trimethoxybenzoate. It belongs to the product categories of Miscellaneous Natural Products; Alkaloids; Biochemistry; Indole Alkaloids; Dopaminergics; Neurotransmitters; Others; Asymmetric Synthesis; Chiral Building Blocks; Complex Molecules; Aromatics; Chiral Reagents; Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals. Its EINECS registry number is 200-047-9. This chemical's molecular formula is C₃₃H₄₀N₂O₉ and molecular weight is 608.68. What's more, both its IUPAC name and systematic name are the same which is called Methyl (3β,16β,17α,18β,20α)-11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylate. Reserpine is an indole alkaloid antipsychotic and antihypertensive drug that has been used for the control of high blood pressure and for the relief of psychotic symptoms.

Physical properties about Reserpine are: (1)ACD/LogP: 4.447; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 2.71; (4)ACD/LogD (pH 7.4): 4.22; (5)ACD/BCF (pH 5.5): 25.79; (6)ACD/BCF (pH 7.4): 827.34; (7)ACD/KOC (pH 5.5): 114.26; (8)ACD/KOC (pH 7.4): 3665.46; (9)#H bond acceptors: 11; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 10; (12)Polar Surface Area: 117.78 Å²; (13)Index of Refraction: 1.62; (14)Molar Refractivity: 160.936 cm³; (15)Molar Volume: 458.165 cm³; (16)Polarizability: 63.8×10^-24cm³; (17)Surface Tension: 59.87 dyne/cm; (18)Density: 1.329 g/cm³; (19)Flash Point: 377.182 °C; (20)Enthalpy of Vaporization: 102.482 kJ/mol; (21)Boiling Point: 700.058 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.

Uses of Reserpine: it is used to produce other chemicals. For example, it can produce 2,11-dimethoxy-3-(3,4,5-trimethoxy-benzoyloxy)-1,2,3,4,4a,5,7,8,8a,13,13a,13b,14,14a-tetradecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester. This reaction needs reagent NaBH₃CN and solvent trifluoroacetic acid at ambient temperature. The reaction time is 1 hour. The yield is 55 %.

Reserpine can produce 2,11-dimethoxy-3-(3,4,5-trimethoxy-benzoyloxy)-1,2,3,4,4a,5,7,8,8a,13,13a,13b,14,14a-tetradecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester.

When you are dealing with this chemical, you should be very careful. This chemical may cause damage to health and may cause inflammation to the skin or other mucous membranes. It is flammable and it is harmful if swallowed. In addition, it is irritating to eyes and the vapours may cause drowsiness and dizziness. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C(OC)[C@H]6[C@H]4C[C@@H]3c2nc1cc(OC)ccc1c2CCN3C[C@H]4C[C@@H](OC(=O)c5cc(OC)c(OC)c(OC)c5)[C@@H]6OC
(2) InChI: InChI=1S/C33H40N2O9/c1-38-19-7-8-20-21-9-10-35-16-18-13-27(44-32(36)17-11-25(39-2)30(41-4)26(12-17)40-3)31(42-5)28(33(37)43-6)22(18)15-24(35)29(21)34-23(20)14-19/h7-8,11-12,14,18,22,24,27-28,31,34H,9-10,13,15-16H2,1-6H3/t18-,22+,24-,27-,28+,31+/m1/s1
(3) InChIKey: QEVHRUUCFGRFIF-MDEJGZGSSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
bird - wild	LD50	oral	100mg/kg (100mg/kg)		Toxicology and Applied Pharmacology. Vol. 21, Pg. 315, 1972.
dog	LD50	intravenous	500ug/kg (.5mg/kg)		"Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 234, 1973.
guinea pig	LD50	subcutaneous	65mg/kg (65mg/kg)		Archives Internationales de Pharmacodynamie et de Therapie. Vol. 137, Pg. 375, 1962.
guinea pig	LDLo	intravenous	16mg/kg (16mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 23, Pg. 600, 1973.
mouse	LD50	intraperitoneal	5mg/kg (5mg/kg)		European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 10, Pg. 519, 1975.
mouse	LD50	intravenous	21mg/kg (21mg/kg)	GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)	Arzneimittel-Forschung. Drug Research. Vol. 14, Pg. 1040, 1964.
mouse	LD50	oral	> 50mg/kg (50mg/kg)		Drugs in Japan Vol. -, Pg. 1453, 1995.
mouse	LD50	subcutaneous	5610ug/kg (5.61mg/kg)		Drugs in Japan Vol. -, Pg. 1453, 1995.
rabbit	LD50	intraperitoneal	7mg/kg (7mg/kg)		Journal of Drug Research. Vol. 6(3), Pg. 19, 1974.
rabbit	LD50	intravenous	15mg/kg (15mg/kg)		"Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 111, 1972.
rat	LD50	intraperitoneal	44mg/kg (44mg/kg)	BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS	Archives Internationales de Pharmacodynamie et de Therapie. Vol. 110, Pg. 20, 1957.
rat	LD50	intravenous	15mg/kg (15mg/kg)		"Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 111, 1972.
rat	LD50	oral	420mg/kg (420mg/kg)	BEHAVIORAL: ANTIPSYCHOTIC	Pesticide Science. Vol. 11, Pg. 555, 1980.
rat	LD50	subcutaneous	25mg/kg (25mg/kg)		Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 56, Pg. 377, 1960.

Product Name

Reserpine

Synthetic route

Reserpine History

Reserpine Consensus Reports

Reserpine Specification

Related Products

Hot Products