4-(3-(2-Chlor-10H-phenothiazin-10-yl)propyl)-1-piperazinethanol

Bezeichnung:4-(3-(2-Chlor-10H-phenothiazin-10-yl)propyl)-1-piperazinethanol

CAS-Nr58-39-9

Englisch Name:PERPHENAZINE

CBNumberCB6687009

SummenformelC21H26ClN3OS

Molgewicht403.97

MOL-Datei58-39-9.mol

Synonyma

Perphenazin

4-(3-(2-Chlor-10H-phenothiazin-10-yl)propyl)-1-piperazinethanol

4-(3-(2-Chlor-10H-phenothiazin-10-yl)propyl)-1-piperazinethanol physikalisch-chemischer Eigenschaften

Schmelzpunkt	95-98?C
Siedepunkt	bp0.15 214-218°; bp1 278-281°
Dichte	1.253
Brechungsindex	1.6100 (estimate)
storage temp.	2-8°C
Löslichkeit	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)
Farbe	White
Wasserlöslichkeit	28.28mg/L(24 ºC)
Merck	14,7183
Stabilität	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 Datenbank	58-39-9(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	22-43
S-Sätze:	28-36/37/39-45
RIDADR	UN 2811 6.1 / PGII
WGK Germany	3
RTECS-Nr.	TL7175000
HS Code	29349990
Giftige Stoffe Daten	58-39-9(Hazardous Substances Data)
Toxizität	LD50 oral in rat: 318mg/kg

Gefahreninformationscode (GHS)

PERPHENAZINE Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R43:Sensibilisierung durch Hautkontakt möglich.
S-Sätze Betriebsanweisung:
S28:Bei Berührung mit der Haut sofort abwaschen mit viel . . . (vom Hersteller anzugeben).
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
Beschreibung
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
Chemische Eigenschaften
Off-White to Pale Yellow Solid
Originator
Trilafon, Schering ,US ,1957
Verwenden
D2 dopamine receptor antagonist; α-adrenergic receptor antagonist and σ-receptor agonist; phenothiazine antipsychotic. Inhibits glutamate dehydrogenase in vitro. Antipsychotic.
Verwenden
immune suppressant, antifungal
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.
Trademarks
Trilafon (Schering).
Therapeutic Function
Tranquilizer
Allgemeine Beschreibung
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.
Sicherheitsprofil
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-.
Einzelnachweise
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 Upstream-Materialien And Downstream Produkte

4-(3-(2-Chlor-10H-phenothiazin-10-yl)propyl)-1-piperazinethanol Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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