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19794-93-5

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19794-93-5 Usage

Chemical Properties

Brown Oil

Originator

Trittico,Angelini,Italy,1972

Uses

Different sources of media describe the Uses of 19794-93-5 differently. You can refer to the following data:
1. Antidepressant
2. 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.

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.

Check Digit Verification of cas no

The CAS Registry Mumber 19794-93-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,9,7,9 and 4 respectively; the second part has 2 digits, 9 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 19794-93:
(7*1)+(6*9)+(5*7)+(4*9)+(3*4)+(2*9)+(1*3)=165
165 % 10 = 5
So 19794-93-5 is a valid CAS Registry Number.
InChI:InChI=1/C19H22ClN5O/c20-16-5-3-6-17(15-16)23-13-11-22(12-14-23)8-4-10-25-19(26)24-9-2-1-7-18(24)21-25/h1-3,5-7,9,15H,4,8,10-14H2

19794-93-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name trazodone

1.2 Other means of identification

Product number -
Other names Trazodil

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:19794-93-5 SDS

19794-93-5Related news

Mutagenicity and recombinogenicity evaluation of bupropion hydrochloride and Trazodone (cas 19794-93-5) hydrochloride in somatic cells of Drosophila melanogaster09/28/2019

The aim of the present study was to appraise the mutagenic and recombinogenic potential of bupropion hydrochloride (BHc) and trazodone hydrochloride (THc). We used standard (ST) and the high bioactivation (HB) crossings from Drosophila melanogaster in the Somatic Mutation and Recombination Test....detailed

Postmortem distribution of Trazodone (cas 19794-93-5) concentrations09/27/2019

Non-toxic postmortem trazodone tissue (liver) concentrations have not been previously described. Liver trazodone concentrations were compared to peripheral blood and central blood concentrations in 19 medical examiner cases. Postmortem blood specimens were initially screened for alcohol and simp...detailed

Alleviating the hepatotoxicity of Trazodone (cas 19794-93-5) via supramolecular encapsulation09/25/2019

In order to develop a novel strategy to alleviate the inherent hepatotoxicity of antidepressant trazodone (TZ), Cucurbit[7]uril (CB[7]) was adopted as pharmaceutical excipients and was studied for its capability to reduce the hepatotoxicity of TZ via supramolecular encapsulation. CB[7] was found...detailed

RESEARCH PAPEREffect of oral Trazodone (cas 19794-93-5) on the minimum alveolar concentration of isoflurane in dogs09/24/2019

ObjectiveTo determine the effect of oral trazodone on the minimum alveolar concentration (MAC) of isoflurane in dogs.detailed

19794-93-5Relevant articles and documents

CONTINUOUS PROCESS FOR THE PREPARATION OF TRAZODONE

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Page/Page column 25-29, (2019/08/29)

The present invention relates to an improved process for the preparation of trazodone. In particular, the present invention relates to a continuous process for the preparation of trazodone. More in particular, the present invention relates to a new method for the preparation of trazodone, said method comprising at least one step consisting of a continuous process performed in a flow reactor.

METHOD FOR THE PREPARATION OF TRAZODONE

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Page/Page column 4, (2018/10/19)

A method for the preparation of trazodone of formula III, in the reaction of 2-(3- halogenopropyl)[l,2,4]triazolo[4,3-a]pyridin-3(2H)-one of formula la or formula lb with l-(3-chlorophenyl)piperazine hydrochloride of formula II consists in, that the reaction of trazodone synthesis is carried out under solvent-free conditions, in the presence of microwave radiation. The reaction is carried out at the molar ratio of 2-(3- halogenopropyl)[l,2,4]triazolo[4,3-a]pyridin-3(2H)-one to l-(3- chlorophenyl)piperazine hydrochloride of from 1 : 1 to 1.2, and using potassium carbonate having the graining of 20 - 900 μηι, which amount in the reaction mixture is from 35 to 45 % by weight of the mixture, and using a PTC catalyst selected from TBAB (tetrabutylammonium bromide), TEAC (tetraethylammonium chloride), DABCO (l,4-diazabicyclo[2.2.2]octane), in an amount of 1 to 4 % by weight of the mixture. After the synthesis is completed, to the reaction mixture water is added and stirred and then the liquid phase is separated from the containing trazodone solid phase.

Efficient copper-catalyzed cross-coupling of 1-Boc-piperazine with aryl iodides and its application in the synthesis of trazodone

Yong, Fui-Fong,Teo, Yong-Chua,Tan, Khee-Ngiap

, p. 5332 - 5334 (2013/09/12)

A convenient and practical strategy is developed for the cross-coupling of N-Boc protected piperazines with aryl iodides using CuBr/1,1′-bi-2- naphthol as the catalyst and K3PO4 as the base. The protocol affords N-arylated piperazine products in moderate to good yields under the optimized conditions. The application of this catalytic system to the synthesis of trazodone is also successfully demonstrated using commercially available substrates.

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