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HomeProduct name listNefazodone hydrochloride

Nefazodone hydrochloride

Synonym(s):2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-5-ethyl- 2,4-dihydro-4-(2-phenoxyethyl)-3H-1,2,4-triazol-3-one hydrochloride;Serzone

Nefazodone hydrochloride Structural

What is Nefazodone hydrochloride?

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.)

The Uses of Nefazodone hydrochloride

A selective serotonin 5-HT2 receptor antagonist. A novel antidepressant that shows no cardiac toxicity or anticholinergic activity common with tricyclic antidepressants.

The Uses of Nefazodone hydrochloride

An antidepressant acts by modifying serotonin transmission. Mixed 5-HT2A serotonin receptor antagonist/serotonin uptake inhibitor

What are the applications of Application

Nefazodone hydrochloride is a SR-2A antagonist

Definition

ChEBI: Nefazodone hydrochloride is a hydrochloride. It contains a nefazodone.

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.

Properties of Nefazodone hydrochloride

Melting point: 186-188°C
storage temp.  Inert atmosphere,Room Temperature
solubility  DMSO: ~11 mg/mL at 60 °C
form  solid
color  white
λmax 248nm(MeOH)(lit.)
Merck  14,6438
CAS DataBase Reference 82752-99-6(CAS DataBase Reference)

Safety information for Nefazodone hydrochloride

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for Nefazodone hydrochloride

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