Amisulpride CAS 71675-85-9
Introduction：Basic information about Amisulpride CAS 71675-85-9, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Amisulpride Basic information
| Product Name: | Amisulpride |
| Synonyms: | 4-amino-n-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-2-methoxybenzam;benzamide,4-amino-n-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-2-metho;Amisulpride, 1000ppm;Sulamid;DAN-2163, Deniban, 4-Amino-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-(ethylsulfonyl)-2-methoxybenzamide;Benzamide, 4-amino-N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-2-methoxy-;4-Amino-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-(ethylsulfonyl)-2-benzamide;4-aMino-5-(ethanesulfonyl)-N-{[(2S)-1-ethylpyrrolidin-2-yl]Methyl}-2-MethoxybenzaMide |
| CAS: | 71675-85-9 |
| MF: | C17H27N3O4S |
| MW: | 369.48 |
| EINECS: | 275-831-7 |
| Product Categories: | DENIBAN;Dopamine receptor;Active Pharmaceutical Ingredients;Antipsychotic;Drug Analogues;Intermediates & Fine Chemicals;Pharmaceuticals |
| Mol File: | 71675-85-9.mol |
Amisulpride Chemical Properties
| Melting point | 124-128 |
| Boiling point | 558.9±50.0 °C(Predicted) |
| density | 1.200±0.06 g/cm3(Predicted) |
| storage temp. | 2-8°C |
| solubility | DMSO: ≥5 mg/mL |
| form | solid |
| pka | 13.73±0.46(Predicted) |
| color | white |
| Merck | 14,485 |
| Major Application | pharmaceutical (small molecule) |
| InChI | InChI=1S/C17H27N3O4S/c1-4-20-8-6-7-12(20)11-19-17(21)13-9-16(25(22,23)5-2)14(18)10-15(13)24-3/h9-10,12H,4-8,11,18H2,1-3H3,(H,19,21) |
| InChIKey | NTJOBXMMWNYJFB-UHFFFAOYSA-N |
| SMILES | C(NCC1CCCN1CC)(=O)C1=CC(S(CC)(=O)=O)=C(N)C=C1OC |
| CAS DataBase Reference | 71675-85-9(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xn |
| Risk Statements | 22 |
| Safety Statements | 22-24/25 |
| WGK Germany | 3 |
| RTECS | CV2308701 |
| HS Code | 2933.99.8290 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Oral |
| Toxicity | LD50 in male mice (mg/kg): 56-60 i.v.; 175-180 i.p.; 224-250 s.c.; 1024-1054 orally (Thominet) |
| Description | Amisulpride i s a n antipsychotic agent structurally related to sulpiride and sultopride. Useful in the treatment of schizophrenia, it is not, however, without EPS liability. |
| Chemical Properties | Off-White Solid |
| Originator | SESIF (Delagrange) (France) |
| Uses | Neuroleptic agent, an analogue of sulpiride. Used as an antipsychotic. Dopamine receptor antagonist |
| Uses | Amisulpride is a neuroleptic agent, an analogue of Sulpiride (S689145). Amisulpride is used as an antipsychotic. Amisulpride is a dopamine receptor antagonist. |
| Definition | ChEBI: Amisulpride is a member of the class of benzamides resulting from the formal condensation of the carboxy group of 4-amino-5-(ethylsulfonyl)-2-methoxybenzoic acid with the primary amino group of 2-(aminomethyl)-1-ethylpyrrolidine. It is a potent, selective dopamine D2 and D3 receptor antagonist. It is an atypical antipsychotic/antischizophrenic agent with limited extrapyrimidal side effects. It has a role as a second generation antipsychotic, a xenobiotic and an environmental contaminant. It is a member of pyrrolidines, an aromatic amine, a sulfone, a member of benzamides and an aromatic amide. |
| Manufacturing Process | 2-Methoxy-4-amino-5-ethylthiobenzoic acid: 159 g of 2-methoxy-4-amino-5-mercaptobenzoic acid, 355 ml of water and160 ml of caustic soda solution are placed in a flask fitted with a condenser.The mixture is heated until the solid dissolves, then 123 g of ethyl sulfate isadded. The mixture is heated to reflux, treated with 10 ml of 30% causticsoda solution, then heated to reflux for 1 hour. After cooling, 800 ml of wateris added and the solution is filtered. The precipitate obtained by adding 100ml of concentrated hydrochloric acid in the presence of ether is drained,washed with water and dried. 162 g of 2-methoxy-4-amino-5-ethylthiobenzoicacid is obtained (yield=88%). 2-Methoxy-4-amino-5-ethylsulfonylbenzoic acid: 123 g of 2-methoxy-4-amino-5-ethylthiobenzoic acid is dissolved hot in 542ml of acetic acid. The solution obtained is cooled to 35°C, then 185 ml ofhydrogen peroxide is added in small quantities while the temperature is raisedto 80°C. The temperature is lowered to 40°C and the mixture is kept at thattemperature for some hours and then cooled to 10°C. The precipitate formedis drained, washed with acetic acid and dried, then dissolved in 600 ml ofwater and 100 ml of 20% ammonia. The precipitate formed by adding 70 mlof concentrated hydrochloric acid is cooled, drained, washed with water anddried. 61.5 g of 2-methoxy-4-amino-5-ethylsulfonylbenzoic acid is obtained(yield 42%, M.P. 95-100°C). 4-Amino-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-(ethylsulfonyl)-2-methoxybenzamide: 81 g of 2-methoxy-4-amino-5-ethylsulphonylbenzoic acid and 297 ml ofacetone are placed in a flask fitted with an agitator, a thermometer and adropping funnel, followed by 33 g of triethylamine. The solution is cooled to0°C, then 30 g of ethyl chloroformate is added drop by drop between 0° and5°C. When the mixture has been agitated 51 g of 1-ethyl-2-aminomethylpyrrolidine is added drop by drop between 5° and 10°C. Themixture is agitated at 10°C then at ambient temperature. The triethylaminehydrochloride which precipitates is drained, then the acetone is distilled. Theresidue is dissolved in 600 ml of water in the presence of caustic soda solution. The base crystallizes after seeding and is drained, washed with waterand dried. When the crystals have been purified by passing them throughhydrochloride and recrystallising them in acetone, 66 g of 4-amino-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-(ethylsulfonyl)-2-methoxybenzamideis obtained(yield 61%, M.P. 126-127°C). |
| Brand name | SOCIAN |
| Therapeutic Function | Antipsychotic |
| Biological Activity | Potent, selective dopamine D 2 and D 3 receptor antagonist. K i values are 2.8 and 3.2 nM respectively for human D 2 and D 3 and > 1000 nM for human D 1 , D 4 and D 5 receptors. Shows selectivity for presynaptic dopamine autoreceptors at low doses and blocks postsynaptic D 2 /D 3 receptors at higher doses. Preferentially interacts with limbic D 2 -like receptors in vivo . Atypical antipsychotic/antischizophrenic agent with limited extrapyrimidal side effects and a profile distinct from that of haloperidol and remoxipride. |
| Biochem/physiol Actions | Amisulpride is a highly selective D2/D3 dopamine receptor antagonist and atypical antipsychotic. |
| Clinical Use | Treatment of acute and chronic schizophrenia |
| Drug interactions | Potentially hazardous interactions with other drugs Alcohol: may enhance CNS effects of alcohol. Anaesthetics: enhanced hypotensive effect. Analgesics: increased risk of convulsions with tramadol; enhanced hypotensive and sedative effects with opioids; increased risk of ventricular arrhythmias with methadone - avoid. Anti-arrhythmics: increased risk of ventricular arrhythmias with anti-arrhythmics that prolong the QT interval; avoid with amiodarone, disopyramide and procainamide (risk of ventricular arrhythmias). Antibacterials: avoid with erythromycin (increased risk of ventricular arrhythmias). Antidepressants: increased level of tricyclics. Antiepileptics: antagonises anticonvulsant effect. Antihypertensives: increased risk of hypotension. Antimalarials: avoid with artemether/lumefantrine. Antipsychotics: increased risk of ventricular arrhythmias with droperidol, sertindole - avoid. Antivirals: concentration possibly increased by ritonavir. Anxiolytics and hypnotics: increased sedative effects. Atomoxetine: increased risk of ventricular arrhythmias. Beta-blockers: increased risk of ventricular arrhythmias with sotalol. Cytotoxics: increased risk of ventricular arrhythmias with vandetanib - avoid; increased risk of ventricular arrhythmias with arsenic trioxide. Diuretics: increased risk of ventricular arrhythmias due to hypokalaemia. Pentamidine: increased risk of ventricular arrhythmias - avoid. |
| Metabolism | Amisulpride is weakly metabolised: two inactive metabolites, accounting for approximately 4% of the dose, have been identified. Amisulpride is eliminated unchanged in the urine. Fifty percent of an intravenous dose is excreted via the urine, of which 90% is eliminated in the first 24 hours. |
| storage | -20°C |
| references | [1] schoemaker h1, claustre y, fage d, rouquier l, chergui k, curet o, oblin a, gonon f, carter c, benavides j, scatton b. neurochemical characteristics of amisulpride, an atypical dopamine d2/d3 receptor antagonist with both presynaptic and limbic selectivity. j pharmacol exp ther. 1997 jan;280(1):83-97. |
Amisulpride Preparation Products And Raw materials
| Raw materials | Diethyl sulfate-->Sodium hydroxide-->2-METHOXY-4-AMINO-5-MERCAPTOBENZOIC ACID |
