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Trazodone

Trazodone
Trazodone structure
CAS No.
19794-93-5
Chemical Name:
Trazodone
Synonyms
trazon;desyrel;razodone;TRAZODONE;trialodine;Trazodone-d6;Trazodone free base;Trazodone USP/EP/BP;Trazodone Impurity 37;Trazodone (base and/or unspecified salts)
CBNumber:
CB3727463
Molecular Formula:
C19H22ClN5O
Formula Weight:
371.86
MOL File:
19794-93-5.mol

Trazodone Properties

Melting point:
86-870C
Boiling point:
528.5±60.0 °C(Predicted)
Density 
1.3141 (rough estimate)
refractive index 
1.5790 (estimate)
pka
pKa (50% ethanol): 6.14(at 25℃)
CAS DataBase Reference
19794-93-5(CAS DataBase Reference)
FDA UNII
YBK48BXK30
NCI Dictionary of Cancer Terms
trazodone
ATC code
N06AX05
NIST Chemistry Reference
Desyrel(trazodone hcl salt)(19794-93-5)
EPA Substance Registry System
1,2,4-Triazolo[4,3-a]pyridin-3(2H)-one, 2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]- (19794-93-5)
SAFETY
  • Risk and Safety Statements
RIDADR  3249
HazardClass  6.1(b)
PackingGroup  III

Trazodone price More Price(6)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Usbiological T8268 Trazodone-d6 19794-93-5 1mg $460 2021-12-16 Buy
Usbiological 227198 Trazodone 19794-93-5 500ul $654 2021-12-16 Buy
AK Scientific M979 Trazodone 19794-93-5 1g $732 2021-12-16 Buy
American Custom Chemicals Corporation RDL0007184 TRAZODONE-D6 95.00% 19794-93-5 5MG $495.45 2021-12-16 Buy
Matrix Scientific 093114 Trazodone 95+% 19794-93-5 250mg $185 2021-12-16 Buy

Trazodone Chemical Properties,Uses,Production

Chemical Properties

Brown Oil

Originator

Trittico,Angelini,Italy,1972

Uses

Antidepressant

Uses

It is believed that trazodone, in therapeutic doses, inhibits the neuronal reuptake of serotonin. It is not a MAO inhibitor or a CNS stimulator. It has a minor influence on the reuptake of norepinephrine and dopamine. In addition, it does not bind with cholinergic or α-adrenergic receptors.

Definition

ChEBI: An N-arylpiperazine in which one nitrogen is substituted by a 3-chlorophenyl group, while the other is substituted by a 3-(3-oxo[1,2,4]triazolo[4,3-a]pyridin-2(3H)-yl)propyl group.

Indications

Trazodone (Apothecon) is also classified as an antidepressant agent. It is a selective serotonin reuptake inhibitor (SSRI), partial agonist at postsynaptic 5-HT1A receptors, and exhibits α-adrenoceptor blocking actions.
Trazodone may cause priapism and enhance libido, and it prolongs nocturnal erections. This drug has been used both orally and by intracavernosal injection. It can be used alone or in combination with yohimbine. Overall, trazodone has not been as effective in treating ED as other available agents. However, it may be an option for selected patients, particularly those with performance anxiety or low libido.

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.

brand name

Beneficat;Bimaran;Deprax;Devidone;Manegan;Molipaxin;Pragmarel;Pragmazone;Taxagon;Thittico;Thombran;Thromban;Tombran;Tramensan;Tritico;Trittico.

Therapeutic Function

Tranquilizer

World Health Organization (WHO)

Trazodone, an antidepressant indicated for the treatment of a wide range of depressive illness, was introduced in 1973. Although it is registered for use in many countries with highly evolved regulatory authorities, approval for registration was not granted in Norway because of a suspicion of carcinogenicity in a two-year rat study.

Biological Functions

Trazodone (Desyrel) was introduced in the early 1980s as a second-generation antidepressant. It blocks the neuronal reuptake of serotonin and is an antagonist at the 5HT2-receptor. Also, its major metabolite, mchlorophenylpiperazine (mCPP), is a postsynaptic serotonin receptor agonist. When compared to the TCAs, trazodone is relatively free of antimuscarinic side effects, but it does block the α-adrenoceptor. Common side effects include marked sedation, dizziness, orthostatic hypotension, and nausea. Priapism is an uncommon but serious side effect requiring surgical intervention in one-third of the cases reported. Because of trazodone’s sedating quality, it is often used in low doses to counter the insomnia associated with the newer antidepressants, such as the SSRIs.

Mechanism of action

Trazodone acts as an antagonist at 5-HT2A receptors and is a weak inhibitor of 5-HT reuptake at the presynaptic neuronal membrane, potentiating the synaptic effects of 5-HT. Its mechanism of action is complicated by the presence of its metabolite, m-chlorophenylpiperazine, which is a 5-HT2C agonist. At therapeutic dosages, trazodone does not appear to influence the reuptake of dopamine or NE within the CNS. It has little anticholinergic activity and is relatively devoid of toxic cardiovascular effects. The increase in serotonergic activity with long-term administration of trazodone decreases the number of postsynaptic serotonergic (i.e., 5-HT2) and β-adrenergic binding sites in the brains of animals, decreasing the sensitivity of adenylate (or adenylyl) cyclase to stimulation by β-adrenergic agonists. It has been suggested that postsynaptic serotonergic receptor modification is mainly responsible for the antidepressant action observed during long-term administration of trazodone. Trazodone does not inhibit MAO and, unlike amphetamine-like drugs, does not stimulate the CNS.
Trazodone is rapidly and almost completely absorbed from the GItract following oral administration, with an oral bioavailability of approximately 65%. Peak plasma concentrations of trazodone occur approximately 1 hour after oral administration when taken on an empty stomach or 2 hours when taken with food. At steady state, its plasma concentrations exhibit wide interpatient variation.
Trazodone is extensively metabolized in the liver by N-dealkylation to its primary active metabolite, m-chlorophenylpiperazine (m-CPP), which subsequently undergoes aromatic hydroxylation to p-hydroxy-m-CPP. In vitro studies indicate that CYP3A4 is the major isoform involved in the production of m-CPP from trazodone (and CYP2D6 to a lesser extent). The p-hydroxy-m-CPP and oxotriazolopyridine-propionic acid (the major metabolite excreted in urine) are conjugated with glucuronic acid. Less than 1% of a dose is excreted unmetabolized.

Clinical Use

Trazodone is a phenylpiperazine–triazolopyridine antidepressant that is structurally unrelated to most of the other antidepressant classes.Trazodone is used primarily in the treatment of insomnia, mental depression, or depression/anxiety disorders. The drug also has shown some efficacy in the treatment of benzodiazepine or alcohol dependence, diabetic neuropathy, and panic disorders.

Chemical Synthesis

Trazodone, 2-[3-[4-(m-chlorophenyl)-1-piperazineyl]propyl]-s-triazolo[4,3-a] piridine-3(2H)-one (7.3.8), is synthesized from 2-chloropiridine, the reaction of which with semicarbazide gives s-triazolo-3-one[4,3-a]pyridine (7.3.7). Alkylation of this product using 1-(3-chloropropyl)-4-(3-chlorophenyl)piperazine gives trazodone (7.3.8) [61,62].

Drug interactions

Trazodone possesses serotonergic activity; therefore, the possibility of developing 5-HT syndrome should be considered in patients who are receiving trazodone and other SSRIs or serotonergic drugs concurrently. When trazodone is used concurrently with drugs metabolized by CYP3A4, caution should be used to avoid excessive sedation. Trazodone can cause hypotension, including orthostatic hypotension and syncope; concomitant administration of antihypertensive therapy may require a reduction in dosage of the antihypertensive agent.

Trazodone Preparation Products And Raw materials

Raw materials

Preparation Products


Trazodone Suppliers

Global( 96)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com China 22607 55
Alchem Pharmtech,Inc.
8485655694
sales@alchempharmtech.com United States 63726 58
CONIER CHEM AND PHARMA LIMITED
86-18523575427
sales@conier.com China 47498 58
career henan chemical co
15093356674 0371-55982848
0086-371-86658258 factory@coreychem.com CHINA 29863 58
Hefei TNJ Chemical Industry Co.,Ltd.
0551-65418671
0551-65418697 sales@tnjchem.com CHINA 37441 58
ShenZhen Ipure Biology import and export company co.,ltd
18071025641 18071025641
eric@ipurechemical.com CHINA 11336 58
Dideu Industries Group Limited
029-88380327
Service@dideu.com CHINA 30014 58
sgtlifesciences pvt ltd
+917013299288
dj@sgtlifesciences.com China 12386 58
Amadis Chemical Company Limited
0086-571-89925085
0086-571-89925065 sales@amadischem.com China 132148 58
Mainchem Co., Ltd. +86-0592-6210733
+86-0592-6210733 sale@mainchem.com CHINA 32439 55

View Lastest Price from Trazodone manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-07-27 Trazodone USP/EP/BP
19794-93-5
US $1.10 / g 1g 99.9% 100 Tons min Dideu Industries Group Limited
2020-01-05 Trazodone
19794-93-5
US $7.00 / KG 1KG 99% 100KG Career Henan Chemical Co

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