Trazodone

Base Information

• Chemical Name: Trazodone
• CAS No.: 19794-93-5
• Molecular Formula: C19H22ClN5O
• Molecular Weight: 371.87
• Hs Code.: 2934.90
• European Community (EC) Number: 243-317-1
• UNII: YBK48BXK30
• DSSTox Substance ID: DTXSID5045043
• Nikkaji Number: J10.767K
• Wikipedia: Trazodone
• Wikidata: Q411457
• NCI Thesaurus Code: C29510
• RXCUI: 10737
• Pharos Ligand ID: FW1VGBK4QFK5
• Metabolomics Workbench ID: 42974
• ChEMBL ID: CHEMBL621
• Mol file: 19794-93-5.mol

Synonyms:AF 1161;AF-1161;AF1161;Apo Trazodone;Apo-Trazodone;Deprax;Desyrel;Gen Trazodone;Gen-Trazodone;Molipaxin;Novo Trazodone;Novo-Trazodone;Nu Trazodone;Nu-Trazodone;PMS Trazodone;PMS-Trazodone;ratio Trazodone;ratio-Trazodone;RatioTrazodone;Thombran;Tradozone;Trazodon Hexal;Trazodon neuraxpharm;Trazodon-neuraxpharm;Trazodone;Trazodone Hydrochloride;TrazodonNeuraxpharm;Trazon;Trittico

Chemical Property of Trazodone

Chemical Property:

• Appearance/Colour: Brown oil
• Vapor Pressure: 2.94E-11mmHg at 25°C
• Melting Point: 86-87oC
• Refractive Index: 1.67
• Boiling Point: 528.532 °C at 760 mmHg
• PKA: pKa (50% ethanol): 6.14(at 25℃)
• Flash Point: 273.446 °C
• PSA: 45.78000
• Density: 1.334 g/cm³
• LogP: 3.16660
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 371.1512880
• Heavy Atom Count: 26
• Complexity: 611

Purity/Quality:

99.9% ^*data from raw suppliers

Trazodone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antidepressant Agents
• Canonical SMILES: C1CN(CCN1CCCN2C(=O)N3C=CC=CC3=N2)C4=CC(=CC=C4)Cl
• Recent ClinicalTrials: Trazodone vs. Quetiapine for the Treatment of ICU Delirium
• Recent EU Clinical Trials: Efficacy of Trazodone Once-a-Day for treatment of Major Depressive Disorder in patients with breast cancer.
• Uses: Antidepressant 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.
• 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.
• Therapeutic Function: Tranquilizer
• 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.
• 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.
• 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.

Technology Process of Trazodone

There total 14 articles about Trazodone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

1-(3-chloropropyl)-4-(3-chlorophenyl)piperazine hydrochloride (52605-52-4) + [1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (6969-71-7) → trazodone (19794-93-5)

Guidance literature:

With sodium hydroxide; In isopropyl alcohol; for 26h; Reagent/catalyst; Inert atmosphere; Reflux;

Reference yield: 90.0%

1-(3-chlorophenyl)piperazine hydrochloride (13078-15-4,51639-49-7,65369-76-8) + 2-(3-chloropropyl)-1,2,4-triazolo<4,3-a>pyridin-3-one (19666-40-1) → trazodone (19794-93-5)

Guidance literature:

With tetrabutylammomium bromide; potassium carbonate; for 0.0833333h; Microwave irradiation;

Reference yield: 71.0%

1-(3-chlorophenyl)piperazine hydrochloride (13078-15-4,51639-49-7,65369-76-8) + 1.3-chlorobromopropane (109-70-6) + [1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (6969-71-7) → trazodone (19794-93-5)

Guidance literature:

1.3-chlorobromopropane; [1,2,4]triazolo[4,3-a]pyridin-3(2H)-one; With tetrabutylammomium bromide; potassium carbonate; In acetonitrile; for 0.0138889h; Microwave irradiation;

1-(3-chlorophenyl)piperazine hydrochloride; In acetonitrile; for 0.025h; Microwave irradiation;

DOI:10.3390/molecules24081609

upstream raw materials:

1-(3-chloro-phenyl)-4-[3-(3-oxo-[1,2,4]triazolo[4,3-a]pyridin-2-yl)-propionyl]-piperazine

1-(3-bromopropyl)-4-(3-chlorophenyl)-piperazine

[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

3-iodochlorobenzene

Downstream raw materials:

C₁₉H₁₈ClN₅O₃

C₁₉H₂₀ClN₅O₃

trazodone hydrochloride

Refernces

• 1、 -. "CONTINUOUS PROCESS FOR THE PREPARATION OF TRAZODONE". . . Retrieved 2019/08/29.
• 2、 -. "Preparation method of trazodone hydrochloride". Paragraph 0042; 0043. . Retrieved 2016/12/01.