82752-99-6 Usage
Description
Nefazodone hydrochloride is a second-generation trazodone-type antidepressant that acts as a potent 5-HT2 receptor antagonist and a serotonin (5-HT) reuptake inhibitor. This dual action enhances 5-HT1A-mediated neurotransmission, providing selective serotonergic effects with minimal affinity for cholinergic and histamine receptors and low affinity for α1-adrenergic receptors. As a result, nefazodone hydrochloride offers a superior toxicity profile, free from agitation, insomnia, and cardiac side effects.
Uses
Used in Pharmaceutical Industry:
Nefazodone hydrochloride is used as an antidepressant for treating depression. It functions by modifying serotonin transmission, offering a mixed 5-HT2A serotonin receptor antagonist and serotonin uptake inhibitor profile.
Used in Antidepressant Therapy:
Nefazodone hydrochloride is used as a selective serotonin 5-HT2 receptor antagonist, providing a novel antidepressant option that avoids the common cardiac toxicity and anticholinergic activity associated with tricyclic antidepressants.
Originator
Bristol-Myers Squibb (U.S.A.)
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).
Therapeutic Function
Antidepressant
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.
Check Digit Verification of cas no
The CAS Registry Mumber 82752-99-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,2,7,5 and 2 respectively; the second part has 2 digits, 9 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 82752-99:
(7*8)+(6*2)+(5*7)+(4*5)+(3*2)+(2*9)+(1*9)=156
156 % 10 = 6
So 82752-99-6 is a valid CAS Registry Number.
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
82752-99-6Relevant articles and documents
Process for the preparation of nefazodone hydrochloride
-
, (2008/06/13)
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
-
, (2008/06/13)
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.