ChemicalBook > CAS DataBase List > PERPHENAZINE

PERPHENAZINE

Product Name: PERPHENAZINE
CAS No.: 58-39-9
Chemical Name: PERPHENAZINE
Synonyms: Trilafon;Perfenazina;Perphenazin;PZC;F-mon;sch3940;Decentan;Emesinal;Fentazin;Sch 3940
CBNumber: CB6687009
Molecular Formula: C21H26ClN3OS
Formula Weight: 403.97
MOL File: 58-39-9.mol

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PERPHENAZINE Property

Melting point:: 95-98?C
Boiling point:: bp0.15 214-218°; bp1 278-281°
Density: 1.253
refractive index: 1.6100 (estimate)
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.
form: Solid
pka: pKa 7.8(H2O,t =24±1) (Uncertain)
color: White
Water Solubility: 28.28mg/L(24 ºC)
Merck: 14,7183
Stability:: Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
InChI: InChI=1S/C21H26ClN3OS/c22-17-6-7-21-19(16-17)25(18-4-1-2-5-20(18)27-21)9-3-8-23-10-12-24(13-11-23)14-15-26/h1-2,4-7,16,26H,3,8-15H2
InChIKey: RGCVKNLCSQQDEP-UHFFFAOYSA-N
SMILES: N1(CCO)CCN(CCCN2C3=CC(Cl)=CC=C3SC3=C2C=CC=C3)CC1
CAS DataBase Reference: 58-39-9(CAS DataBase Reference)

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Safety

Hazard Codes: Xn
Risk Statements: 22-43
Safety Statements: 28-36/37/39-45
RIDADR: UN 2811 6.1 / PGII
WGK Germany: 3
RTECS: TL7175000
HS Code: 29349990
Hazardous Substances Data: 58-39-9(Hazardous Substances Data)
Toxicity: LD50 oral in rat: 318mg/kg

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H317May cause an allergic skin reaction

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: Y0001045
Product name: Perphenazine for system suitability
Purity: European Pharmacopoeia (EP) Reference Standard
Packaging: 5 mg
Price: $118
Updated: 2025/07/31

Sigma-Aldrich

Product number: P6402
Product name: Perphenazine
Packaging: 1g
Price: $90.06
Updated: 2025/07/31

Sigma-Aldrich

Product number: PHR3079
Product name: Perphenazine
Purity: pharmaceutical secondary standard, certified reference material
Packaging: 500MG
Price: $265.05
Updated: 2025/07/31

Sigma-Aldrich

Product number: P-130
Product name: Perphenazine solution
Purity: 1?mg/mL in methanol (), certified reference material, ampule of 1?mL, Cerilliant?
Packaging: 1mL
Price: $149
Updated: 2025/07/31

Sigma-Aldrich

Product number: P0550000
Product name: Perphenazine
Purity: European Pharmacopoeia (EP) Reference Standard
Packaging: 100 mg
Price: $156
Updated: 2025/07/31

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PERPHENAZINE Chemical Properties,Usage,Production

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

Chemical Properties

Off-White to Pale Yellow Solid

Originator

Trilafon, Schering ,US ,1957

Uses

immune suppressant, antifungal

Uses

D2 dopamine receptor antagonist; α-adrenergic receptor antagonist and σ-receptor agonist; phenothiazine antipsychotic. Inhibits glutamate dehydrogenase in vitro. Antipsychotic.

Definition

ChEBI: A phenothiazine derivative in which the phenothiazine tricycle carries a chloro substituent at the 2-position and a 3-[4-(2-hydroxyethyl)piperazin-1-yl]propyl group at N-10.

Manufacturing Process

A mixture of 155 parts of 2-chloro-10-(γ-chloropropyl)phenothiazine, 76 partsof sodium iodide, 216 parts of piperazine and 2,000 parts of butanone is refluxed for 8 hours, concentrated and extracted with dilute hydrochloric acid. The extract is rendered alkaline by addition of dilute potassium carbonate and benzene or chloroform extracted. This extract is washed with water, dried over anhydrous potassium carbonate, filtered and evaporated. Vacuum distillation at 0.1 mm pressure yields 2-chloro-10-[γ-(N-piperazino)propyl]phenothiazine at about 214°-218°C.
A stirred mixture of 5 parts of 2-chloro-10-[γ-(Npiperazino)propyl]phenothiazine, 1.92 parts of 2-bromoethanol, 2.11 parts of potassium carbonate and 35 parts of toluene is refluxed for 5 hours. The mixture is treated with water and benzene and the organic layer is separated, washed with water, dried over anhydrous potassium carbonate, filtered and evaporated. The residue is distilled at about 240°-244°C and 0.15 mm pressure to yield 2-chloro-10-[γ-(N'-β-hydroxyethyl-N-piperazino)propyl]phenothiazine according to US Patent 2,838,507.
The 2-chloro-10-(γ-chloropropyl)phenothiazine starting material is produced from 2-chlorophenothiazine and 1-bromo-3-chloropropane.

brand name

Trilafon (Schering).

Therapeutic Function

Tranquilizer

General Description

Perphenazine, 4-[3-(2-chlorophenothiazine-10-yl)propyl]piperazineethanol; 2-chloro-10-[3-[4-(2-hydroxyethyl)piperazinyl]propyl]phenothiazine(Trilafon), is an effective antipsychotic and antiemetic.

Biochem/physiol Actions

D2 dopamine receptor antagonist; α-adrenergic receptor antagonist and σ-receptor agonist; phenothiazine antipsychotic. Inhibits glutamate dehydrogenase in vitro.

Safety Profile

Poison by ingestion, intravenous, subcutaneous, intraperitoneal, and intramuscular routes. Human systemic effects by intramuscular route: muscle spasms. Experimental teratogenic and reproductive effects. Human mutation data reported. When heated to decomposition it emits very toxic fumes of SOx, NOx, and cl-.

References

[1] ANDREW J GOUDIE. H1-histamine Receptor Affinity Predicts Short-term Weight Gain for Typical and Atypical Antipsychotic Drugs[J]. Neuropsychopharmacology, 2003, 28 12: 2209-2209. DOI:10.1038/sj.npp.1300291
[2] JOHANNES KORNHUBER. Identification of novel functional inhibitors of acid sphingomyelinase.[J]. ACS Applied Bio Materials, 2011: e23852. DOI:10.1371/journal.pone.0023852
[3] OMER F KUZU. Modulating cancer cell survival by targeting intracellular cholesterol transport[J]. British Journal of Cancer, 2017, 117 4: 513-524. DOI:10.1038/bjc.2017.200
[4] IVAN COUÉE Keith F T. Inhibition of ox brain glutamate dehydrogenase by perphenazine[J]. Biochemical pharmacology, 1990, 39 7: Pages 1167-1173. DOI:10.1016/0006-2952(90)90258-m

PERPHENAZINE Preparation Products And Raw materials

Raw materials

2-Chlorophenothiazine Prochlorperazine 1-Bromo-3-chloropropane

Preparation Products

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View Lastest Price from PERPHENAZINE manufacturers

Baoji Guokang Healthchem Co., Ltd.

Product: PERPHENAZINE 58-39-9
Price: US $415.00/Kg/Bag
Min. Order: 1KG
Purity: 99%
Supply Ability: 1T
Release date: 2021-06-03

Zhuozhou Wenxi import and Export Co., Ltd

Product: perphenazine 58-39-9
Price: US $15.00-10.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-07-08

Zhuozhou Wenxi import and Export Co., Ltd

Product: PERPHENAZINE 58-39-9
Price: US $415.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-07-03

58-39-9, PERPHENAZINERelated Search:

Perphenazine-17-N-Oxide DiHCl Perphenazine impurity Perphenazine-14-N-Oxide PERPHENAZINE Methophenazine thiopropazate Chlorpromazine Prochlorperazine 2-Chlorophenothiazine PERPHENAZINE SULFOXIDE (100 MG),Perphenazine sulfoxide PERPHENAZINE HCL,Perphenazine hydrochloride PERPHENAZINE-D4 (PHENOTHIAZINE-1,3,7,9-D4) perphenazine decanoate perphenazine enanthate amitriptyline-perphenazine combination PERPHENAZINE-D4 PERPHENAZINE SULPHOXIDE Perphenazine maleate,Perphenazine dimaleate

1-(2-Hydroxyethyl)-4-(3-(2-chloro-10-phenothiazinyl)propyl)piperazine

1',1-(2-Idrossietil)-4,3-(2-cloro-10-fenotiazil)propilpiperazina

1’,1-(2-idrossietil)-4,3-(2-cloro-10-fenotiazil)propilpiperazina

1-Piperazineethanol, 4-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]-

1-Piperazineethanol, 4-[3-(2-Chlorophenothiazin-10-yl)propyl]-

2-(4-[3-(2-Chloro-10H-phenothiazin-10-yl)propyl]-1-piperazinyl)ethanol

2-Chloro-10-(3-(4-(2-hydroxyethyl)piperazin-1-yl)propyl)phenothiazine

2-chloro-10-[3-[1-(2-hydroxyethyl)-4-piperazinyl]propyl]phenothiazine

2-Chloro-10-3-(1-(2-hydroxyethyl)-4-piperazinyl)propyl phenothiazine

2-[4-[3-(2-chloro-10H-phenothiazin-10-yl) propyl]piperazin-1-yl]ethanol

Perphenazine (200 mg)K0F0180.998mg/mg(dr)

Perphenazine (200 mg)

Chloriprozine

4-[3-(2-Chloro-10H-phenothiazin-10-yl)propyl]-1-piperazineethanol

Perphenazine, >=99%

2-chloro-10-3-(1-(2-hydroxyethyl)-4-piperazinyl)propylphenothiazine

4(3-(2-chloro-10h-phenothiazin-10-yl)propyl)-1-piperazineethano

4-(3-(2-chlorophenothiazin-10-yl)propyl)-1-piperazineethano

4-(3-(2-Chlorophenothiazin-10-yl)propyl)-1-piperazineethanol

4-[3-(2-chloro-10h-phenothiazin-10yl)propyl]-1-piperazineethano

4-[3-(2-chlorophenothiazin-10-yl)propyl]-1-piperazineethanol

Chlorperphenazine

chlorpiprazine

component of Etrafon

Decentan

Emesinal

Etaperazin

Etaperazine

PERPHENAZINE USP

Chlorpiprozine

Perphenazine solution

Fluphenazine Dihydrochloride EP Impurity E

2-{4-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]piperazin-1-yl}ethan-1-ol

Ethaperazine

Fentazin

F-mon

gamma-(4-(beta-Hydroxyethyl)piperazin-1-yl)propyl-2-chlorophenothiazine

Perfenazina

Perfenazine

Perphenan

Perphenazin

Piperazineethanol, 4-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]-

PZC

Sch 3940

sch3940

Thilatazin

Tranquisan

Trifaron

Trilafon

Trilifan

Triphenot

PERPHENAZINE

2-(4-(3-(2-chlorophenothiazin-10-yl)propyl)piperazin-1-yl)ethanol

Perphenazine USP&BP

Perpheazine CP2000,BP93

Fluphenazine Dihydrochloride Impurity 5(Fluphenazine Dihydrochloride EP Impurity E)

Perphenazine CRS

Perphenazine RS