2-[3-[4-(3-Chlorphenyl)piperazin-1-y]propyl]-1,2,4-triazolo[4,3-a]pyridin-3(2H)-onhydrochlorid

Bezeichnung:2-[3-[4-(3-Chlorphenyl)piperazin-1-y]propyl]-1,2,4-triazolo[4,3-a]pyridin-3(2H)-onhydrochlorid

CAS-Nr25332-39-2

Englisch Name:Trazodone hydrochloride

CBNumberCB3376874

SummenformelC19H23Cl2N5O

Molgewicht408.32

MOL-Datei25332-39-2.mol

Synonyma

2-[3-[4-(3-Chlorphenyl)piperazin-1-y]propyl]-1,2,4-triazolo[4,3-a]pyridin-3(2H)-onhydrochlorid

2-[3-[4-(3-Chlorphenyl)piperazin-1-y]propyl]-1,2,4-triazolo[4,3-a]pyridin-3(2H)-onhydrochlorid physikalisch-chemischer Eigenschaften

Schmelzpunkt	223-226?C
Flammpunkt	9℃
storage temp.	2-8°C
Löslichkeit	45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 23.3 mg/mL
Aggregatzustand	powder
Farbe	off-white
PH	pH (10g/l, 25℃) : 3.9～4.5
Wasserlöslichkeit	Soluble at 25mg/ml in methanol. Also soluble in 0.1M HCl or DMSO. Insoluble in water /n
InChIKey	OHHDIOKRWWOXMT-UHFFFAOYSA-N
CAS Datenbank	25332-39-2(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xn,Xi,T,F
R-Sätze:	22-40-36/37/38-39/23/24/25-23/24/25-11
S-Sätze:	22-36-37/39-26-45-36/37-16-7
RIDADR	3249
WGK Germany	3
RTECS-Nr.	XZ5660000
HazardClass	6.1(b)
PackingGroup	III
HS Code	29335990
Toxizität	LD50 i.v. in mice: 96 mg/kg (Silvestrini, Quadri)

Gefahreninformationscode (GHS)

Trazodone hydrochloride Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R40:Verdacht auf krebserzeugende Wirkung.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
Chemische Eigenschaften
White to Off-White Solid
Originator
Trittico,Angelini,Italy,1972
Verwenden
A serotonin uptake inhibitor
Verwenden
antihistamine
Verwenden
Monoamine reuptake inhibitor; antidepressant.
Definition
ChEBI: A hydrochloride salt prepared from equimolar amounts of trazodone and hydrogen chloride.
Manufacturing Process
In an initial step, 2-chloropyridine is reacted with semicarbazide to give s_x0002_triazolo-[4,3-a]-pyridine-3-one. To a boiling solution of 6.7 grams s-triazolo-[4,3-a]-pyridine-3-one in 80 ml dioxane, there is added 2.4 grams 50% NaH. The mixture is refluxed during 1 hour under stirring, then 13.5 grams 1-(3-chloropropyl)-4-mchlorophenylpiperazine is added. The mixture is refluxed under stirring for 20 hours, cooled, diluted with an equal volume of ether, the sodium chloride filtered out, and ethereal HCl added. The solid which precipitates is filtered out and crystallized from 95% alcohol. Yield is 13.5 grams, MP 223°C. The following is an alternative method of preparation: 1 gram 2-(γ- chloropropyl)-s-triazolo-[4,3-a]-pyridine-3-one and 5 ml saturated ammonia alcoholic solution are heated for 5 hours in a closed tube at 100°C. The contents of the tube are cooled, the ammonium chloride filtered out and the solvent is removed. There remains a residue of 0.9 grams 2-(γ-aminopropyl)- s-triazolo-[4,3-a]-pyridine-3-one.
This residue is dissolved in isopropyl alcohol and 1 gram N-bis-chloroethylaniline is added to it. The mixture is refluxed for 3 hours. The solvent is removed at a reduced pressure, the residue is treated with 50% potassium carbonate, and extracted with ether. By treating with ethereal hydrochloric acid, 2-N'-m-chlorophenylpiperazino-propyl-s-triazole[4,3-a]pyridine-3-one hydrochloride is precipitated; MP 223°C.
Therapeutic Function
Tranquilizer
Allgemeine Beschreibung
Trazodone is a antidepressant drug sold under trade names such as Desyrel^? and Oleptro^? for treatment of anxiety disorder, depression, and insomnia. Trazadone, a serotonin antagonist and reuptake inhibitor (SARI), also has anti-anxiety and hypnotic effects. This certified Snap-N-Spike^? solution is suitable for use in clinical toxicology, forensic analysis, or urine drug testing methods by LC-MS/MS or GC/MS.
Biochem/physiol Actions
Antidepressant that potentiates the activity of serotonin uptake blockers and has full 5-HT2C serotonin receptor agonist activity. It is metabolized to the 5-HT1 serotonin receptor agonist 1-(3-Chlorophenyl)piperazine.
Clinical Use
Tricyclic-related antidepressant
Arzneimittelwechselwirkung
Potentially hazardous interactions with other drugs
Alcohol: increased sedative effects.
Antidepressants: avoid concomitant use with MAOIs and moclobemide.
Antiepileptics: antagonism of anticonvulsant effect; concentration reduced by carbamazepine.
Antimalarials: manufacturer advises avoid concomitant use with artemether and lumefantrine and piperaquine with artenimol.
Antivirals: concentration increased by ritonavir; increased risk of ventricular arrhythmias with saquinavir - avoid; concentration possibly increased by telaprevir.
Stoffwechsel
Trazodone is hepatically metabolised via the cytochrome P450 isoenzyme CYP3A4 by n-oxidation and hydroxylation. The metabolite m-chlorophenylpiperazine is active. Trazodone is excreted in the urine almost entirely in the form of its metabolites.
Lager
Store at RT

Trazodone hydrochloride Upstream-Materialien And Downstream Produkte

2-[3-[4-(3-Chlorphenyl)piperazin-1-y]propyl]-1,2,4-triazolo[4,3-a]pyridin-3(2H)-onhydrochlorid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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