CAS No.71675-85-9,Amisulpride Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	71675-85-9
Name:	Amisulpride
Article Data:	9
Cas Database

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

Synthetic route

: 26116-12-1
1-ethyl-2-pyrrolidinemethanamine

: 541-41-3
chloroformic acid ethyl ester

: 71675-85-9
amisulpride

Conditions

Conditions	Yield
In triethylamine; acetone	100%
In triethylamine; acetone	84%

: 26116-12-1
1-ethyl-2-pyrrolidinemethanamine

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

: 71675-85-9
amisulpride

Conditions

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

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

: 71675-85-9
amisulpride

Conditions

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

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

Conditions	Yield
With triethylamine In water; acetone	61%

...Expand

: 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

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%

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%

: 74-96-4
ethyl bromide

: C19H29N3O5S

: 71675-85-9
amisulpride

Conditions

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

: 1-ethyl-2-aminomethylpyrrolidine hydrochloride

: 71675-85-9
amisulpride

Conditions

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

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

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

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

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

Raw Materials

541-41-3

65-49-6

Total:209 Page 1 of 6 1 2 3 4 5 6 Next>>

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Chemistry

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

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)	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): Harmful 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