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| CAS No.: | 71675-85-9 |
|---|---|
| Name: | Amisulpride |
| Molecular Structure: | |
|
|
|
| Formula: | C17H27N3O4S |
| Molecular Weight: | 369.485 |
| Synonyms: | 4-Amino-N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-o-anisamide;Aminosultopride;4-amino-N-[(1-ethylpyrrolidin-2-yl)methyl]-5-ethylsulfonyl-2-methoxy-benzamide;Amisulprida [INN-Spanish];Benzamide, 4-amino-N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-2-methoxy-;Benzamide,4-amino-N-[(1-ethyl-2- pyrrolidinyl)methyl]-5-(ethylsulfonyl)-2- methoxy-;4-Amino-N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-2-anisamid;4-Amino-N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-2-methoxybenzamide;Amisulpridum [INN-Latin];Solian;DAN 2163;Methyl ammonia mosapride; |
| EINECS: | 275-831-7 |
| Density: | 1.2 g/cm3 |
| Melting Point: | 124-128 °C |
| Boiling Point: | 558.9 °C at 760 mmHg |
| Flash Point: | 291.8 °C |
| Solubility: | DMSO: ≥5 mg/mL |
| Appearance: | Off-white solid |
| Hazard Symbols: |
 Xn
|
| Risk Codes: | 22 |
| Safety: | 22-24/25 |
| PSA: | 110.11000 |
| LogP: | 3.27590 |
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- 71825-51-92-methyl-2-(4-nitrophenyl)propanenitrile
- 26116-12-1
1-ethyl-2-pyrrolidinemethanamine
- 541-41-3
chloroformic acid ethyl ester
- 71675-85-9
amisulpride
| Conditions | Yield |
|---|---|
| In triethylamine; acetone | 100% |
| In triethylamine; acetone | 84% |
- 26116-12-1
1-ethyl-2-pyrrolidinemethanamine
- 71675-85-9
amisulpride
| Conditions | Yield |
|---|---|
| With potassium tert-butylate In tert-butyl alcohol at 83℃; for 20h; Reagent/catalyst; Solvent; Temperature; | 96.5% |
- 26116-12-1
1-ethyl-2-pyrrolidinemethanamine
- 71675-85-9
amisulpride
| Conditions | Yield |
|---|---|
| In dichloromethane at 20 - 40℃; for 6h; Temperature; | 89.4% |
- 26116-12-1
1-ethyl-2-pyrrolidinemethanamine
- 71675-87-1
2-methoxy-4-amino-5-ethylsulphonyl benzoic acid
- 71675-85-9
amisulpride
| Conditions | Yield |
|---|---|
| Stage #1: 2-methoxy-4-amino-5-ethylsulphonyl benzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 10 - 20℃; for 1.5h; Stage #2: 1-ethyl-2-pyrrolidinemethanamine With triethylamine In acetonitrile at 80℃; for 2h; | 86.8% |
| With C36H24B4N2O3 In toluene for 14h; Molecular sieve; Reflux; chemoselective reaction; | 76% |
| With chloroformic acid ethyl ester; triethylamine In acetone at 0 - 30℃; | 70% |
- 26116-12-1
1-ethyl-2-pyrrolidinemethanamine
- 71675-87-1
2-methoxy-4-amino-5-ethylsulphonyl benzoic acid
- 541-41-3
chloroformic acid ethyl ester
- 71675-85-9
amisulpride
| Conditions | Yield |
|---|---|
| With triethylamine In water; acetone | 61% |
- 74-96-4
ethyl bromide
- 176849-91-5
4-amino-N-(1-ethyl-pyrrolidin-2-ylmethyl)-5-iodo-2-methoxy-benzamide
- 71675-85-9
amisulpride
| Conditions | Yield |
|---|---|
| Stage #1: ethyl bromide; 4-amino-N-(1-ethyl-pyrrolidin-2-ylmethyl)-5-iodo-2-methoxy-benzamide With 1,1'-bis-(diphenylphosphino)ferrocene; sodium metabisulfite; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tin; potassium hydrogenphosphate trihydrate; tetrabutylammomium bromide In dimethyl sulfoxide at 100℃; for 10h; Inert atmosphere; Schlenk technique; Stage #2: With potassium carbonate In methanol at 20℃; for 2h; | 61% |
| Conditions | Yield |
|---|---|
| Stage #1: ethyl bromide; C19H29N3O5S With 1,1'-bis-(diphenylphosphino)ferrocene; sodium metabisulfite; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tin; potassium hydrogenphosphate trihydrate; tetrabutylammomium bromide In dimethyl sulfoxide at 100℃; for 10h; Inert atmosphere; Stage #2: With potassium carbonate In methanol at 20℃; for 2h; | 61% |
- 71675-87-1
2-methoxy-4-amino-5-ethylsulphonyl benzoic acid
- 71675-85-9
amisulpride
| Conditions | Yield |
|---|---|
| Stage #1: 2-methoxy-4-amino-5-ethylsulphonyl benzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 0.5h; Stage #2: 1-ethyl-2-aminomethylpyrrolidine hydrochloride With triethylamine In dichloromethane at 20℃; | 29.7% |
- 27492-84-8
Methyl 4-amino-2-methoxybenzoate
- 71675-85-9
amisulpride
| Conditions | Yield |
|---|---|
| Multi-step reaction with 5 steps 1.1: bromine / methanol / 5 - 15 °C / Industry scale 2.1: sodium sulfide / water; acetone / 5 - 15 °C / Industry scale 3.1: sodium hydroxide; water / methanol / 65 °C / Industry scale 3.2: 5 - 10 °C / pH 4 - 4.5 / Industry scale 4.1: dihydrogen peroxide / sodium tungstate / water; methanol / 5 h / 20 - 30 °C 5.1: chloroformic acid ethyl ester; triethylamine / acetone / 0 - 30 °C View Scheme | |
| Multi-step reaction with 4 steps 1.1: bromine / methanol / 5 - 15 °C / Industry scale 2.1: sodium sulfide / water; acetone / 5 - 15 °C / Industry scale 3.1: dihydrogen peroxide / sodium tungstate / isopropyl alcohol / 40 - 45 °C / Industry scale 3.2: 60 - 65 °C / Industry scale 3.3: pH 4 - 4.5 / Industry scale 4.1: chloroformic acid ethyl ester; triethylamine / acetone / 0 - 30 °C View Scheme |
- 65-49-6
4-Aminosalicylic acid
- 71675-85-9
amisulpride
| Conditions | Yield |
|---|---|
| Multi-step reaction with 6 steps 1.1: potassium hydroxide; tetrabutylammomium bromide / acetone / 1 h / 25 - 35 °C / Industry scale 2.1: bromine / methanol / 5 - 15 °C / Industry scale 3.1: sodium sulfide / water; acetone / 5 - 15 °C / Industry scale 4.1: sodium hydroxide; water / methanol / 65 °C / Industry scale 4.2: 5 - 10 °C / pH 4 - 4.5 / Industry scale 5.1: dihydrogen peroxide / sodium tungstate / water; methanol / 5 h / 20 - 30 °C 6.1: chloroformic acid ethyl ester; triethylamine / acetone / 0 - 30 °C View Scheme | |
| Multi-step reaction with 5 steps 1.1: potassium hydroxide; tetrabutylammomium bromide / acetone / 1 h / 25 - 35 °C / Industry scale 2.1: bromine / methanol / 5 - 15 °C / Industry scale 3.1: sodium sulfide / water; acetone / 5 - 15 °C / Industry scale 4.1: dihydrogen peroxide / sodium tungstate / isopropyl alcohol / 40 - 45 °C / Industry scale 4.2: 60 - 65 °C / Industry scale 4.3: pH 4 - 4.5 / Industry scale 5.1: chloroformic acid ethyl ester; triethylamine / acetone / 0 - 30 °C View Scheme |
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Chemistry
Molecular Structure:
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Molecular Formula: C17H27N3O4S
Molecular Weight: 369.479
IUPAC Name: 4-Amino-N-[(1-ethylpyrrolidin-2-yl)methyl]-5-ethylsulfonyl-2-methoxybenzamide
Synonyms of Amisulpride (CAS NO.71675-85-9): Amisulpride [INN] ; Sultopride ; 4-Amino-N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-2-anisamid ; 4-Amino-N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-2-methoxybenzamide ; 4-Amino-N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-o-anisamide ; Aminosultopride ; Amisulprida ; Amisulprida [INN-Spanish] ; Amisulpridum ; Amisulpridum [INN-Latin] ; DAN 2163 ; EINECS 275-831-7 ; Solian ; Sulpitac ; UNII-8110R61I4U ; Benzamide, 4-amino-N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-2-methoxy-
CAS NO: 71675-85-9
Classification Code: Drug / Therapeutic Agent
Melting Point: 124-128 °C
Index of Refraction: 1.545
Molar Refractivity: 97.43 cm3
Molar Volume: 307.7 cm3
Surface Tension: 44.9 dyne/cm
Density: 1.2 g/cm3
Flash Point: 291.8 °C
Enthalpy of Vaporization: 84.11 kJ/mol
Boiling Point: 558.9 °C at 760 mmHg
Vapour Pressure: 1.59E-12 mmHg at 25°C
Uses
Amisulpride (CAS NO.71675-85-9) is a neuroleptic agent and an analogue of sulpiride. Amisulpride is used as an antipsychotic. It is a DOPAMINE receptor antagonist.
Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LD50 | intraperitoneal | 175mg/kg (175mg/kg) | United States Patent Document. Vol. #4401822, | |
| mouse | LD50 | intravenous | 56mg/kg (56mg/kg) | United States Patent Document. Vol. #4401822, | |
| mouse | LD50 | oral | 1024mg/kg (1024mg/kg) | United States Patent Document. Vol. #4401822, | |
| mouse | LD50 | subcutaneous | 224mg/kg (224mg/kg) | United States Patent Document. Vol. #4401822, |
Safety Profile
Hazard Codes of Amisulpride (CAS NO.71675-85-9): 
Xn
Risk Statements: 22
R22: Harmful if swallowed.
Safety Statements: 22-24/25
S22: Do not breathe dust.
S24/25: Avoid contact with skin and eyes.
WGK Germany: 3
RTECS: CV2308701