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PERPHENAZINE

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PERPHENAZINE Basic information

Product Name:
PERPHENAZINE
Synonyms:
  • 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
CAS:
58-39-9
MF:
C21H26ClN3OS
MW:
403.97
EINECS:
200-381-5
Product Categories:
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Mol File:
58-39-9.mol
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PERPHENAZINE Chemical Properties

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.
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.
CAS DataBase Reference
58-39-9(CAS DataBase Reference)
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Safety Information

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

MSDS

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PERPHENAZINE Usage And Synthesis

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) Kroeze et al. (2003), H1-Histamine Receptor Affinity Predicts Short-Term Weight Gain for Typical and Atypical Antipsychotic Drugs; Neuropharmacology, 28 519 2) Kornhuber et al. (2011), Identification of Novel Functional Inhibitors of Acid Sphingomyelinase; PLoS One, 6 e23852 3) Kuzu et al. (2017), Modulating cancer cell survival by targeting intracellular cholesterol transport; Br. J. Cancer,?117 513 4) Couee and Tipton (1990), Inhibition of ox brain glutamate by perphenazine; Biochem. Pharmacol. 39 1167

PERPHENAZINE Preparation Products And Raw materials

Raw materials

PERPHENAZINESupplier

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