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Amisulpride
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Name

Amisulpride

 EINECS 275-831-7
CAS No. 71675-85-9 Density 1.2 g/cm3
PSA 110.11000 LogP 3.27590
Solubility DMSO: ≥5 mg/mL Melting Point 124-128 °C
Formula C17H27N3O4S Boiling Point 558.9 °C at 760 mmHg
Molecular Weight 369.485 Flash Point 291.8 °C
Transport Information N/A Appearance Off-white solid
Safety 22-24/25 Risk Codes 22
Molecular Structure Molecular Structure of 71675-85-9 (Amisulpride) Hazard Symbols HarmfulXn
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;

Article Data 9

Amisulpride Synthetic route

26116-12-1

1-ethyl-2-pyrrolidinemethanamine

541-41-3

chloroformic acid ethyl ester

71675-85-9

amisulpride

Conditions
ConditionsYield
In triethylamine; acetone100%
In triethylamine; acetone84%
26116-12-1

1-ethyl-2-pyrrolidinemethanamine

methyl 4-amino-5-(ethylsulfonyl)-2-methoxybenzoate

71675-85-9

amisulpride

Conditions
ConditionsYield
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

2-methoxy-4-amino-5-ethanesulfonylbenzoyl chloride

71675-85-9

amisulpride

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With triethylamine In water; acetone61%
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
ConditionsYield
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%
74-96-4

ethyl bromide

C19H29N3O5S

71675-85-9

amisulpride

Conditions
ConditionsYield
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

1-ethyl-2-aminomethylpyrrolidine hydrochloride

71675-85-9

amisulpride

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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

Amisulpride Chemical Properties

Molecular Structure:

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

Amisulpride 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.

Amisulpride 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,

Amisulpride Safety Profile

Hazard Codes of Amisulpride (CAS NO.71675-85-9): HarmfulXn
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

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