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HomeProduct name listTrazodone hydrochloride

Trazodone hydrochloride

Synonym(s):2-[3-[4-(3-Chlorophenyl)-1-piperazinyl]propyl]-1,2,4-triazolo[4,3-a]pyridin-3(2H)-one hydrochloride;Trazodone hydrochloride

  • CAS NO.:25332-39-2
  • Empirical Formula: C19H23Cl2N5O
  • Molecular Weight: 408.32
  • MDL number: MFCD00079603
  • EINECS: 246-855-5
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-01 14:32:37
Trazodone hydrochloride Structural

What is Trazodone hydrochloride?

Chemical properties

White to Off-White Solid

Originator

Trittico,Angelini,Italy,1972

The Uses of Trazodone hydrochloride

Monoamine reuptake inhibitor; antidepressant.

The Uses of Trazodone hydrochloride

antihistamine

The Uses of Trazodone hydrochloride

A serotonin uptake inhibitor

What are the applications of Application

Trazodone Hydrochloride is a serotonin antagonist and reuptake inhibitor

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

General Description

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

Drug interactions

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.

Metabolism

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.

storage

Store at RT

Properties of Trazodone hydrochloride

Melting point: 223-226?C
Flash point: 9℃
storage temp.  2-8°C
solubility  45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 23.3 mg/mL
form  powder
color  off-white
PH pH (10g/l, 25℃) : 3.9~4.5
Water Solubility  Soluble at 25mg/ml in methanol. Also soluble in 0.1M HCl or DMSO. Insoluble in water /n
CAS DataBase Reference 25332-39-2(CAS DataBase Reference)

Safety information for Trazodone hydrochloride

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
ghs
Health Hazard
GHS08
GHS Hazard Statements H302:Acute toxicity,oral
H351:Carcinogenicity
Precautionary Statement Codes P280:Wear protective gloves/protective clothing/eye protection/face protection.

Computed Descriptors for Trazodone hydrochloride

InChIKey OHHDIOKRWWOXMT-UHFFFAOYSA-N

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