Sulpiride

Base Information

• Chemical Name: Sulpiride
• CAS No.: 15676-16-1
• Molecular Formula: C15H23N3O4S
• Molecular Weight: 341.431
• Hs Code.: 2935009090
• European Community (EC) Number: 239-753-7
• UNII: 7MNE9M8287
• DSSTox Substance ID: DTXSID1042574
• Nikkaji Number: J3.446K
• Wikipedia: Sulpiride
• Wikidata: Q422418
• NCI Thesaurus Code: C87713
• RXCUI: 10239
• Pharos Ligand ID: LALZ95KS948D
• Metabolomics Workbench ID: 78513
• ChEMBL ID: CHEMBL26
• Mol file: 15676-16-1.mol

Synonyms:Mirbanil;Misulvan;N-[(1-Ethyl-2-pyrrolidinyl)methyl]-2-methoxy-5-sulfamoylbenzamide;Splotin;Sulpirid;Sulpitil;Sulpyrid;Synedil;o-Anisamide,N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-sulfamoyl- (8CI);Abilit;Aiglonyl;

Chemical Property of Sulpiride

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 180-185 °C
• Refractive Index: 1.6320 (estimate)
• PKA: pKa1 9.00, pKa2 10.19(at 25℃)
• PSA: 110.11000
• Density: 1.236 g/cm³
• LogP: 2.66660
• Storage Temp.: 2-8°C
• Solubility.: 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 8.0 mg/mL
• Water Solubility.: <0.21g/L(25 oC)
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 341.14092740
• Heavy Atom Count: 23
• Complexity: 505

Purity/Quality:

99% ^*data from raw suppliers

racSulpiride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCN1CCCC1CNC(=O)C2=C(C=CC(=C2)S(=O)(=O)N)OC
• Recent ClinicalTrials: The Role of Dopamine, Reward Learning and Prefrontal Activity in Expectation-induced Mood Enhancement
• 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
• Uses: Sulpiride is an antipsychotic drug used in the treatment of Schozophrenia and depression. dopamine receptor antagonist, antipsychotic Sulpiride possesses moderate neuroleptic activity along with some stimulating and antidepressant effects. It has antiemetic, moderately cataleptogenic, and antiserotonin action. It facilitates increased blood flow in the stomach. It speeds up the restorative processes in tissues. It is used for schizophrenia, depression, migraines, disturbance of behavioral functions, and stomach and duodenal ulcers.
• Therapeutic Function: Tranquilizer, Digestive aid
• Clinical Use: Antipsychotic: Acute and chronic schizophrenia
• Drug interactions: Potentially hazardous interactions with other drugs Anaesthetics: enhanced hypotensive effect. Analgesics: increased risk of convulsions with tramadol; enhanced hypotensive and sedativeeffects with opioids; increased risk of ventricular arrhythmias with methadone. Anti-arrhythmics increased risk of ventricular arrhythmias with anti-arrhythmics that prolong the QT interval, e.g. procainamide, disopyramide and amiodarone - avoid with amiodarone. Antibacterials: increased risk of ventricular arrhythmias with moxifloxacin and parenteral erythromycin - avoid with moxifloxacin. Antidepressants: possibly increased risk of ventricular arrhythmias and antimuscarinic side effects with tricyclics - avoid. Antiepileptics: antagonism (convulsive threshold lowered). Antimalarials: avoid with artemether/lumefantrine. Antipsychotics: increased risk of ventricular arrhythmias with droperidol, haloperidol and pimozide - avoid; possible increased risk of ventricular arrhythmias with risperidone. Antivirals: concentration possibly increased by ritonavir. Anxiolytics and hypnotics: increased sedative effects. Atomoxetine: increased risk of ventricular arrhythmias. Beta-blockers: enhanced hypotensive effect; 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: enhanced hypotensive effect. Lithium: increased risk of extrapyramidal side effects and possibly neurotoxicity. Pentamidine: increased risk of ventricular arrhythmias.

Technology Process of Sulpiride

There total 11 articles about Sulpiride 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: 93.8%

methyl 2-methoxy-5-sulfamoyl-benzoate (33045-52-2) + (S)-2-(Aminomethyl)-1-ethylpyrrolidine (22795-99-9) → (S)-(-)-sulpiride (15676-16-1,23672-06-2,23672-07-3,23756-79-8)

Guidance literature:

at 90 - 100 ℃; for 5h; Inert atmosphere;

Reference yield: 90.3%

2-methoxy-5-sulfamoylbenzoic acid ethyl ester (33045-53-3) + (S)-2-(Aminomethyl)-1-ethylpyrrolidine (22795-99-9) → (S)-(-)-sulpiride (15676-16-1,23672-06-2,23672-07-3,23756-79-8)

Guidance literature:

In isopropyl alcohol; at 80 ℃; for 36h; Solvent; Temperature;

Reference yield: 88.5%

1-ethyl-2-pyrrolidinemethanamine (26116-12-1) + 2-methoxy-5-sulfamoylbenzoic acid ethyl ester (33045-53-3) → N-[(1-ethyl-2-pyrrolidinyl)methyl]-2-methoxy-5-sulfamoylbenzamide (15676-16-1)

Guidance literature:

In glycerol; at 110 - 120 ℃; for 4h;

upstream raw materials:

1-ethyl-2-pyrrolidinemethanamine

methyl 2-methoxy-5-sulfamoyl-benzoate

1-ethyl-2-(nitromethylene)pyrrolidine

1-hydroxy-pyrrolidine-2,5-dione

Downstream raw materials:

(S)-3-(((1-ethylpyrrolidin-2-yl)methyl)carbamoyl)-4-methoxybenzenesulfonyl azide

[Co(chloride)2(2-methoxy-5-sulphamoyl-N-((1-ethylpyrrolidin-2-yl)methyl)benzamide)2(water)2]*(water)

[Zn(chloride)2(2-methoxy-5-sulphamoyl-N-((1-ethylpyrrolidin-2-yl)methyl)benzamide)2(water)2]

[Fe(chloride)2(2-methoxy-5-sulphamoyl-N-((1-ethylpyrrolidin-2-yl)methyl)benzamide)2(water)2](chloride)*(water)

Refernces

• 1、 -. "Sulfonamide compound and synthesis method and application thereof". Paragraph 0146-0149. . Retrieved 2019/04/02.
• 2、 Wang, Ming,Fan, Qiaoling,Jiang, Xuefeng. "Metal-free construction of primary sulfonamides through three diverse salts". supporting information. p. 5469 - 5473. Retrieved 2019/01/03.