82752-99-6

Basic information

• Product Name: Nefazodone hydrochloride
• Synonyms: NEFAZODONE-D5 HCL;3H-1,2,4-Triazol-3-one, 2-3-4-(3-chlorophenyl)-1-piperazinylpropyl-5-ethyl-2,4-dihydro-4-(2-phenoxyethyl)-, monohydrochloride;Nefazodone HCl;Nefazodone hydrochloride;NEFAZODONE;BMY-13754, MJ-13754-1, Serzone, 2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-5-ethyl- 2,4-dihydro-4-(2-phenoxyethyl)-3H-1,2,4-triazol-3-one hydrochloride;2,4-Dihydro-2-(3-(4-(3-chlorophenyl)-1-piperazinyl)propyl)-5-ethyl-4-(2-phenoxyethyl)-3H-1,2,4-triazol-3-one hydrochloride;Nefazodone hydrochlo
• CAS NO: 82752-99-6
• Molecular Formula: C₂₅H₃₂ClN₅O₂*ClH
• Molecular Weight: 506.47
• Product Categories: Active Pharmaceutical Ingredients;Serotonin receptor;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;API;SERZONE
• Mol File: 82752-99-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: 186-188°C
• Boiling Point: 599.6 °C at 760 mmHg
• Flash Point: 316.4 °C
• Appearance: white/solid
• Vapor Pressure: 2.46E-14mmHg at 25°C
• Storage Temp.: Desiccate at RT
• Solubility: DMSO: ~11 mg/mL at 60 °C
• Merck: 14,6438
• CAS DataBase Reference: Nefazodone hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Nefazodone hydrochloride(82752-99-6)
• EPA Substance Registry System: Nefazodone hydrochloride(82752-99-6)

Safety Data

• Safety Statements: 22-24/25
• RIDADR: UN1230 - class 3 - PG 2 - Methanol, solution
• WGK Germany: 3
• RTECS: XZ5483009
• Hazardous Substances Data: 82752-99-6(Hazardous Substances Data)

Usage

Description

Nefazodone, a second generation trazodone type antidepressant, was launched in Canada. Nefazodone acts as both a potent 5-HT2 receptor antagonist and as a serotonin (5-HT) reuptake inhibitor. This combination effect appears to enhance 5-HTIA-mediated neurotransmission. Distinct from the first generation agents such as tricyclic antidepressants, nefazodone has very selective serotonergic effects with negligible affinity for cholinergic and histamine receptors, and low affinity for a1 -adrenergic receptors. Therefore, it has a superior toxicity profile that does not produce agitation, insomnia, and lacks cardiac side effects.

Chemical Properties

White Solid

Originator

Bristol-Myers Squibb (U.S.A.)

Uses

Different sources of media describe the Uses of 82752-99-6 differently. You can refer to the following data:
1. An antidepressant acts by modifying serotonin transmission. Mixed 5-HT2A serotonin receptor antagonist/serotonin uptake inhibitor
2. A selective serotonin 5-HT2 receptor antagonist. A novel antidepressant that shows no cardiac toxicity or anticholinergic activity common with tricyclic antidepressants.

Manufacturing Process

Manufacturing process for Moxifloxacin hydrochloride includes these steps as follows: 1. synthesis of 1-(3-Chloropropyl)-4-(3-chlorophenyl)piperazine hydrochloride, 1-(3-Chlorophenyl)-4-(hydrazinopropyl)piperazine. 2.Phenoxypropionic acid (249.0 g, 1.50 mol) is dissolved in four equivalents of thionyl chloride (438.0 ml, 6.0 mol) and heated to reflux until the HCl evolution has ceased. The solution is then cooled to room temperature and concentrated under reduced pressure to give 281.0 g (100% yield) of phenoxypropionyl chloride as a brown oil which solidifies on cooling 3.Phenoxypropionyl chloride (9.23 g, 0.05 mol) is dissolved in 100 ml acetone and cooled with an ice bath as sodium azide (3.6 g, 0.055 mol) in 10 ml water is added dropwise. After addition is completed, the reaction mixture is warmed to room temperature and stirred for 30 minutes. The solution is decanted and concentrated. The residue is dissolved in 100 ml ether and washed with saturated sodium bicarbonate and brine. The organic phase is separated, dried (MgSO4) and concentrated to give 6.52 g (68.0% yield) of phenoxypropionyl azide as a yellow oil which solidifies on cooling. 4.Synthesis of Ethyl phenoxypropionate, Phenoxypropionyl hydrazide, Phenoxyethyl isocyanate, 2-3-(4-[3-Chlorophenyl]-1-piperazinyl)propyl]-4-(2-phenoxyethyl)- semicarbazide), and 2-[3-4-(3-Chlorophenyl)-1-piperazinyl]-propyl]-5-ethyl-4-(2-phenoxyethyl)- 2H-1,2,4-triazol-3(4H)-one monohydrochloride (Nefazodone monohydrochloride).

Brand name

Serzone (Bristol-Myers Squibb).

Therapeutic Function

Antidepressant

General Description

Nefazodone, formerly sold under the brand names Serzone, Dutonin, and Nefadar, is an antidepressant that has been discontinued due to the incidence of severe liver damage. This certified Snap-N-Spike; solution is suitable for use as a starting material in calibrators and controls for numerous GC/MS or LC/MS applications in forensic analysis, clinical toxicology and urine drug testing.

Biological Activity

Serotonin 5-HT 2A receptor antagonist (K i = 5.8 nM) and inhibitor of serotonin and noradrenalin uptake (IC 50 values are 290 and 300 nM respectively). Displays no activity at 5-HT 1B and 5-HT 1D receptors. Active in models predictive of antidepressant potential.

Biochem/physiol Actions

Novel antidepressant; mixed 5-HT2A serotonin receptor antagonist/serotonin uptake inhibitor.

InChI:InChI=1/C25H32ClN5O2.ClH/c1-2-24-27-31(25(32)30(24)18-19-33-23-10-4-3-5-11-23)13-7-12-28-14-16-29(17-15-28)22-9-6-8-21(26)20-22;/h3-6,8-11,20H,2,7,12-19H2,1H3;1H

Upstream product

• 95885-13-5 5-ethyl-4-(2-phenoxyethyl)-2H-1,2,4-triazol-3(4H)-one 
• 52605-52-4 1-(3-chloropropyl)-4-(3-chlorophenyl)piperazine hydrochloride 

Relevant articles and documents

Process for the preparation of nefazodone hydrochloride

A process for the preparation of Nefazodone hydrochloride comprising direct conversion of semicarbazide dihydrochloride 3 into Nefazodone hydrochloride which process involves a reaction of triethyl orthopropionate in the presence of trimethylsilylchloride and hydrochloric acid.

1,2,4-TRIAZOL-3-ONE ANTIDEPRESSANTS

Phenoxyalkyl substituted-1,2,4-triazolones having anti-depressant properties typified by 2-3-4-(3-chlorophenyl)-1-piperazinyl!propyl!-5-ethyl-4-(2-phenoxyethyl)-2H-1,2, 4-triazol-3(4H)-one are disclosed.