Perphenazine

Base Information

• Chemical Name: Perphenazine
• CAS No.: 58-39-9
• Molecular Formula: C21H26ClN3OS
• Molecular Weight: 403.976
• Hs Code.: 29349990
• European Community (EC) Number: 200-381-5
• NSC Number: 758649,150866
• UNII: FTA7XXY4EZ
• DSSTox Substance ID: DTXSID1023441
• Nikkaji Number: J1.387K
• Wikipedia: Perphenazine
• Wikidata: Q423520
• NCI Thesaurus Code: C29355
• RXCUI: 8076
• Pharos Ligand ID: W81AQ74N31P3
• Metabolomics Workbench ID: 43132
• ChEMBL ID: CHEMBL567
• Mol file: 58-39-9.mol

Synonyms:Chlorpiprazine;Perfenazine;Perphenazine;Trilafon

Chemical Property of Perphenazine

Chemical Property:

• Appearance/Colour: Off-white to pale yellow solid
• Melting Point: 35339ºC
• Refractive Index: 1.6100 (estimate)
• Boiling Point: 580.4 °C at 760 mmHg
• PKA: pKa 7.8(H2O,t =24±1) (Uncertain)
• Flash Point: 304.8 °C
• PSA: 55.25000
• Density: 1.253 g/cm³
• LogP: 3.88350
• Storage Temp.: 2-8°C
• Solubility.: Practically insoluble in water, freely soluble in methylene chloride, soluble in ethanol (96 per cent). It dissolves in dilute solutions of hydrochloric acid.
• Water Solubility.: 28.28mg/L(24 oC)
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 403.1485113
• Heavy Atom Count: 27
• Complexity: 463

Purity/Quality:

99.9% ^*data from raw suppliers

Perphenazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-43
• Safety Statements: 28-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Antipsychotic Agents
• Canonical SMILES: C1CN(CCN1CCCN2C3=CC=CC=C3SC4=C2C=C(C=C4)Cl)CCO
• Recent ClinicalTrials: Recommendations of Enhanced Recovery Interventions for Patient's Clinical Team and Collection of Associated Data
• Recent EU Clinical Trials: English: Are Antipsychotics Neurotoxic or Neuroprotective? A Randomised Multicentre Longitudinal Study for Comparison of Two Therapy Strategies for the Treatment of Schizophrenia.
• Recent NIPH Clinical Trials: An intervention study of optimizing algorism-based pharmacological treatment for schizophrenia
• Description: Perphenazine (58-39-9) is a clinically useful typical antipsychotic drug. The therapeutic mode of action is not well understood but it binds to a wide variety of receptors including serotonin, histamine, dopamine, and α-adrenergic.1 Perphenazine is an inhibitor of acid sphingomyelinase(ASM)2 and positively affected xenografted tumor growth via perturbation of intracellular cholesterol transport through ASM3. It has also been shown to be an inhibitor of glutamate dehydrogenase.4
• Uses: D2 dopamine receptor antagonist; α-adrenergic receptor antagonist and σ-receptor agonist; phenothiazine antipsychotic. Inhibits glutamate dehydrogenase in vitro. Antipsychotic.
• Therapeutic Function: Tranquilizer

Technology Process of Perphenazine

There total 7 articles about Perphenazine 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:

methanesulfonic acid (75-75-2,98527-29-8) + perphenazine N-Boc-4-aminobutyrate (503537-30-2) → 4-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]-1-piperazineethyl 4-aminobutyryl ester trimesylate + perphenazine (58-39-9)

Guidance literature:

In acetonitrile; at 0 - 40 ℃; for 6h; Product distribution / selectivity;

Reference yield:

N-Demethyl prochlorperazine (40323-85-1) + 2-bromoethanol (540-51-2) → perphenazine (58-39-9)

Guidance literature:

With potassium carbonate; toluene;

Reference yield:

2-chlorophenothiazine (92-39-7) → perphenazine (58-39-9)

Guidance literature:

Multi-step reaction with 2 steps

1: NaNH₂; liquid NH₃

With ammonia; sodium amide;

upstream raw materials:

1-(2-hydroxyethyl)piperazine

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

N-Demethyl prochlorperazine

2-bromoethanol

Downstream raw materials:

1-benzoyloxy-2-{4-[3-(2-chloro-phenothiazin-10-yl)-propyl]-piperazin-1-yl}-ethane

5,6-dhydrouracil

perphenazine N-Boc-4-aminobutyrate

perphenazine-d4

Refernces

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