Amisulpride

Base Information

• Chemical Name: Amisulpride
• CAS No.: 71675-85-9
• Molecular Formula: C17H27N3O4S
• Molecular Weight: 369.485
• Hs Code.: 2933990090
• European Community (EC) Number: 275-831-7
• NSC Number: 760085
• UNII: 8110R61I4U
• DSSTox Substance ID: DTXSID5042613
• Nikkaji Number: J18.603A
• Wikipedia: Amisulpride
• Wikidata: Q418785
• NCI Thesaurus Code: C83533
• RXCUI: 46303
• Pharos Ligand ID: T7K5XUHM4JMY
• Metabolomics Workbench ID: 43669
• ChEMBL ID: CHEMBL243712
• Mol file: 71675-85-9.mol

Synonyms:4-Amino-N-((1-ethyl-2-pyrrolidinyl)methyl)-5-(ethylsulfonyl)-2-methoxybenzamide;amisulpride;Barnetil;DAN 2163;DAN-2163;LIN 1418;LIN-1418;N-(ethyl-1-pyrrolidinyl- 2-methyl)methoxy-2-ethylsulfonyl-5-benzamide;Solian;sultopride;sultopride hydrochloride

Chemical Property of Amisulpride

Chemical Property:

• Appearance/Colour: Off-white solid
• Vapor Pressure: 1.59E-12mmHg at 25°C
• Melting Point: 124-128 °C
• Refractive Index: 1.545
• Boiling Point: 558.9 °C at 760 mmHg
• PKA: 13.73±0.46(Predicted)
• Flash Point: 291.8 °C
• PSA: 110.11000
• Density: 1.2 g/cm³
• LogP: 3.27590
• Storage Temp.: 2-8°C
• Solubility.: DMSO: ≥5 mg/mL
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 369.17222752
• Heavy Atom Count: 25
• Complexity: 549

Purity/Quality:

≥98.0% ^*data from raw suppliers

Amisulpride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCN1CCCC1CNC(=O)C2=CC(=C(C=C2OC)N)S(=O)(=O)CC
• Recent ClinicalTrials: A Study of Intravenous (IV) Amisulpride for Prophylaxis of Post-operative Nausea and Vomiting (PONV) in Pediatric Patients
• Recent EU Clinical Trials: HAMLETT. Handling Antipsychotic Medication: Long-term Evaluation of Targeted Treatment. A pragmatic single blind RCT of continuation versus discontinuation/ dose reduction of antipsychotic medication in patients remitted after a first episode of psychosis
• 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.
• Uses: Neuroleptic agent, an analogue of sulpiride. Used as an antipsychotic. Dopamine receptor antagonist Amisulpride is a neuroleptic agent, an analogue of Sulpiride (S689145). Amisulpride is used as an antipsychotic. Amisulpride is a dopamine receptor antagonist.
• Therapeutic Function: 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.

Technology Process of Amisulpride

There total 13 articles about Amisulpride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

1-ethyl-2-pyrrolidinemethanamine (26116-12-1) + chloroformic acid ethyl ester (541-41-3) → amisulpride (71675-85-9)

Guidance literature:

In triethylamine; acetone;

Reference yield: 96.5%

1-ethyl-2-pyrrolidinemethanamine (26116-12-1) + methyl 4-amino-5-(ethylsulfonyl)-2-methoxybenzoate (80036-89-1) → amisulpride (71675-85-9)

Guidance literature:

With potassium tert-butylate; In tert-butyl alcohol; at 83 ℃; for 20h; Reagent/catalyst; Solvent; Temperature;

Reference yield: 89.4%

1-ethyl-2-pyrrolidinemethanamine (26116-12-1) + 2-methoxy-4-amino-5-ethanesulfonylbenzoyl chloride → amisulpride (71675-85-9)

Guidance literature:

In dichloromethane; at 20 - 40 ℃; for 6h; Temperature;

upstream raw materials:

1-ethyl-2-pyrrolidinemethanamine

chloroformic acid ethyl ester

2-methoxy-4-amino-5-ethylsulphonyl benzoic acid

Methyl 4-amino-2-methoxybenzoate

Downstream raw materials:

(R)-(+)-4-amino-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-(ethylsulfonyl)-2-methoxybenzamide L-tartrate

(S)-(-)-4-amino-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-(ethylsulfonyl)-2-methoxybenzamide D-tartrate

Refernces

• 1、 -. "(S)(-)-amisulpride preparation method". Paragraph 0004. . Retrieved 2020/03/06.
• 2、 -. "Preparation method of amisulpride". Paragraph 0039; 0042-0045; 0048-0049; 0052-0053; 0056; 0058. . Retrieved 2019/12/29.