Trazodone hydrochloride

Trazodone hydrochloride Basic information
Description References
Product Name:Trazodone hydrochloride
Synonyms:TRAZODONE HCL;TRAZODONE HYDROCHLORIDE;)-onehcl;2-(3-(4-(3-chlorophenyl)-1-piperazinyl)propyl)-s-triazolo(4,3-a)pyridin-3(2h;af1161;2-{3-[4-(3-chlorophenyl)piperazin-1-yl]propyl}-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one hydrochloride;TrazodonHCL;Trazodone HCl,trazodone hydrochloride
CAS:25332-39-2
MF:C19H23Cl2N5O
MW:408.32
EINECS:246-855-5
Product Categories:ANAHIST;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;25332-39-2
Mol File:25332-39-2.mol
Trazodone hydrochloride Structure
Trazodone hydrochloride Chemical Properties
Melting point 223-226?C
Fp 9℃
storage temp. 2-8°C
solubility 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 23.3 mg/mL
form powder
color off-white
PHpH (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
InChIKeyOHHDIOKRWWOXMT-UHFFFAOYSA-N
CAS DataBase Reference25332-39-2(CAS DataBase Reference)
Safety Information
Hazard Codes Xn,Xi,T,F
Risk Statements 22-40-36/37/38-39/23/24/25-23/24/25-11
Safety Statements 22-36-37/39-26-45-36/37-16-7
RIDADR 3249
WGK Germany 3
RTECS XZ5660000
HazardClass 6.1(b)
PackingGroup III
HS Code 29335990
ToxicityLD50 i.v. in mice: 96 mg/kg (Silvestrini, Quadri)
MSDS Information
ProviderLanguage
SigmaAldrich English
Trazodone hydrochloride Usage And Synthesis
DescriptionTrazodone Hydrochloride belongs to the hydrochloride salt form of trazodone with antidepressant and sedative activities, which is primarily used in the treatment of major depression. It serves as a serotonin uptake inhibitor that is effective for patients suffering from major depressive disorders and other subsets of depressive disorders, which is especially helpful for geriatric patients with severe agitation and certain depressive disorders associated with insomnia and anxiety since it has proved that trazodone also has anti-anxiety (anxiolytic) and sleep-inducing (hypnotic) effects. Besides, it is often prescribed as a sedative that is used for the treatment of panic attacks, aggressive behavior, agoraphobia, and cocaine withdrawal in combination with other drugs. Trazodone Hydrochloride is an oral drug that functions by affecting the balance of chemicals (neurotransmitters) within the brain that nerves use to communicate with (stimulate) each other.
Referenceshttps://en.wikipedia.org/wiki/Trazodone
http://www.medicinenet.com/trazodone/article.htm
https://www.drugbank.ca/drugs/DB00656
http://bodyandhealth.canada.com/drug/getdrug/ratio-trazodone
https://pubchem.ncbi.nlm.nih.gov/compound/62935#section=Top



Chemical PropertiesWhite to Off-White Solid
OriginatorTrittico,Angelini,Italy,1972
UsesA serotonin uptake inhibitor
Usesantihistamine
UsesMonoamine reuptake inhibitor; antidepressant.
DefinitionChEBI: A hydrochloride salt prepared from equimolar amounts of trazodone and hydrogen chloride.
Manufacturing ProcessIn 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 FunctionTranquilizer
General DescriptionTrazodone 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 ActionsAntidepressant 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 UseTricyclic-related antidepressant
Drug interactionsPotentially 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.




MetabolismTrazodone 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.
storageStore at RT
Trazodone hydrochloride Preparation Products And Raw materials
Raw materials2-Chloropyridine-->Semicarbazide-->Sodium hydride
Trazodone Hydrochloride 2-[3-[4-(3-Chlorophenyl)-1-piperazinyl]propyl]-1,2,4-tri Piperacillin TRAZODONE HYDROCHLORIDE IMPURITY STANDARD Pyridine hydrochloride Propyl gallate TRAZODONE HYDROCHLORIDE IMP. H (BP) AS DIHYDROCHLORIDE: 1,3-BIS-[4-(3-CHLOROPHENYL)PIPERAZIN-1-YL]PROPANE DIHYDROCHLORIDE N-Aminoethylpiperazine Topotecan hydrochloride Trazodone hydrochloride TRAZODONE HYDROCHLORIDE IMP. F (BP) AS HYDROCHLORIDE: 1-(3-CHLOROPHENYL)-4-(3-CHLOROPROPYL)PIPERAZINE HYDROCHLORIDE Sibutramine hydrochloride Tramadol hydrochloride 2-Ethylhexyl ferulate Piperazine Cetirizine hydrochloride 1-AdaMantanethylaMine Homopiperazine Propyl butyrate Trazodone Hcl

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