Prochlorperazine

Base Information

• Chemical Name: Prochlorperazine
• CAS No.: 58-38-8
• Molecular Formula: C20H24 Cl N3 S
• Molecular Weight: 373.95
• European Community (EC) Number: 200-379-4
• UNII: YHP6YLT61T
• DSSTox Substance ID: DTXSID7023514
• Nikkaji Number: J1.386B
• Wikipedia: Prochlorperazine
• Wikidata: Q2359690
• NCI Thesaurus Code: C774
• RXCUI: 8704
• Pharos Ligand ID: J4UYVBWGRUP1
• Metabolomics Workbench ID: 42790
• ChEMBL ID: CHEMBL728
• Mol file: 58-38-8.mol

Synonyms:Compazine;Edisylate Salt, Prochlorperazine;Edisylate, Prochlorperazine;Maleate, Prochlorperazine;Prochlorperazine;Prochlorperazine Edisylate;Prochlorperazine Edisylate Salt;Prochlorperazine Maleate;Salt, Prochlorperazine Edisylate

Chemical Property of Prochlorperazine

Chemical Property:

• Appearance/Colour: Clear, pale yellow, viscous liquid.
• Melting Point: 228 °C
• Refractive Index: 1.6000 (estimate)
• Boiling Point: 524.8°Cat760mmHg
• PKA: pKa 8.1(H2O,t =24±1,I undefined) (Uncertain)
• Flash Point: 271.2°C
• PSA: 35.02000
• Density: 1.217g/cm³
• LogP: 4.52100
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• Water Solubility.: 14.96mg/L(24 oC)
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 373.1379466
• Heavy Atom Count: 25
• Complexity: 429

Purity/Quality:

98%,99%, ^*data from raw suppliers

Prochlorperazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Gastrointestinal Agents; Antipsychotic Agents
• Canonical SMILES: CN1CCN(CC1)CCCN2C3=CC=CC=C3SC4=C2C=C(C=C4)Cl
• Recent ClinicalTrials: Olanzapine for the Prevention of Chemotherapy Induced Nausea and Vomiting in Gynecologic Oncology Patients
• Uses: antiemetic, antipsychotic, treatment of vertigo Prochlorperazine is antiemetic, antipsychotic; used in treatment of vertigo.
• Clinical Use: Nausea and vomiting Labyrinthine disorders Psychoses Severe anxiety
• Drug interactions: Potentially hazardous interactions with other drugs 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. Anti-arrhythmics increased risk of ventricular arrhythmias with anti-arrhythmics that prolong the QT interval, e.g. procainamide, disopyramide, dronedarone and amiodarone - avoid with amiodarone and dronedarone. Antibacterials: increased risk of ventricular arrhythmias with delamanid and moxifloxacin - avoid. Antidepressants: increase concentrations and additive antimuscarinic effects, notably with tricyclics; increased risk of ventricular arrhythmias with citalopram and escitalopram - avoid; increased risk of convulsions with vortioxetine. Antiepileptics: antagonised (convulsive threshold lowered). Antimalarials: avoid with artemether/lumefantrine and piperaquine with artenimol. Antipsychotics: increased risk of ventricular arrhythmias with droperidol and pimozide - avoid; increased risk of ventricular arrhythmias with risperidone. Antivirals: concentration possibly increased with ritonavir; increased risk of ventricular arrhythmias with saquinavir - avoid. 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 arsenic trioxide. Desferrioxamine: avoid concomitant use. Diuretics: enhanced hypotensive effect. Lithium: increased risk of extrapyramidal side effects and possibly neurotoxicity. Pentamidine: increased risk of ventricular arrhythmias.

Technology Process of Prochlorperazine

There total 5 articles about Prochlorperazine 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:

1-methyl-piperazine (109-01-3) + 2-chloro-10-(3-chloropropyl)-10H-phenothiazine (2765-59-5) → prochlorperazine (58-38-8)

Guidance literature:

With sodium hydroxide; In toluene; for 15h; Heating;

Reference yield:

2-chlorophenothiazine (92-39-7) + 3-(4-methyl-1-piperazinyl)propyl chloride dihydrochloride (2031-23-4,77270-74-7) → prochlorperazine (58-38-8)

Guidance literature:

With sodium hydroxide; In toluene; for 15h; Heating;

Reference yield:

→ prochlorperazine (58-38-8)

Guidance literature:

With copper; potassium carbonate; N,N-dimethyl-formamide;

upstream raw materials:

1-methyl-piperazine

2-chloro-10-(3-chloropropyl)-10H-phenothiazine

2-chlorophenothiazine

3-(4-methyl-1-piperazinyl)propyl chloride dihydrochloride

Downstream raw materials:

Prochlorperazine sulfoxide

Refernces

• 1、 Levy,Tozer,Tuck,Loveland. "Stability of some phenothiazine free radicals.". . p. 898 - 905. Retrieved 2007/10/10.