27367-90-4 Usage
Description
Niaprazine is a pharmaceutical compound that serves as a norepinephrine reuptake inhibitor (NRI), a non-myorelaxing hypnotic agent, and a 5-HT2A inverse agonist or antagonist. It is designed to address various medical conditions, including sleep apnea and other related disorders.
Uses
Used in Sleep Apnea Treatment:
Niaprazine is used as a treatment for sleep apnea, a condition characterized by pauses in breathing during sleep. As a 5-HT2A inverse agonist or antagonist, it helps regulate the sleep-wake cycle and improves overall sleep quality.
Used in Attention and Cognitive Enhancement:
Niaprazine, being a norepinephrine reuptake inhibitor (NRI), is used to enhance attention and cognitive functions. By increasing the levels of norepinephrine in the brain, it can improve focus, alertness, and mental clarity.
Used in Non-Myorelaxing Hypnotic Agents:
In the pharmaceutical industry, Niaprazine is used as a non-myorelaxing hypnotic agent. This application helps promote sleep without causing muscle relaxation, making it a suitable option for individuals who require sleep aid without the risk of muscle-related side effects.
Used in Antidepressant Therapy:
Niaprazine, due to its action as a norepinephrine reuptake inhibitor, is also utilized in the treatment of depression. It helps alleviate symptoms by increasing the availability of norepinephrine, which is a neurotransmitter associated with mood regulation and the central nervous system's response to stress.
Originator
Nopron,Carrion,France,1976
Manufacturing Process
1st Stage: 10 ml of concentrated (10 N) hydrochloric acid and 240 ml of
acetone were added to a solution of 217.5 g (1 mol) of 1-(4-
fluorophenyl)piperazine dihydrochloride in 400 ml of 96% ethanol. 50 g of
powdered trioxymethylene were then added and the mixture was then slowly
heated to reflux, which was maintained for 1 hour. A further 60 g of
trioxymethylene were then added and heating to reflux was continued for a
further 6 hours.The mixture was then cooled, the precipitate formed was filtered off, washed
with acetone and recrystallized from 96% ethanol.The base was liberated from its salt by taking up the product in an aqueous
solution of sodium bicarbonate. The precipitate of the base thus obtained was
recrystallized from petroleum ether to give 160 g of the desired product;
melting point 46°C; yield 64%.2nd Stage: 45.5 g (0.65 mol) of hydroxylamine hydrochloride were added to a
solution of 128 g (0.5 mol) of the amino-ketone obtained in the preceding
stage in 100 ml of ethanol and 40 ml of water. The mixture was allowed to
react for 15 minutes at room temperature and was then heated to reflux for
? hour. A part of the solvent was then distilled off and the product was then
allowed to crystallize on cooling. After recrystallization from 96% ethanol, 117
g of the desired product were obtained; melting point 170°C; yield 77%.3rd Stage: 93 g (0.35 mol) of the oxime obtained in the preceding stage, in
the form of the base, were added in portions to a suspension of 17 g (0.45
mol) of lithium aluminum hydride in 400 ml of anhydrous ether. The mixture
was then heated to reflux for 15 hours.10 ml of ethyl acetate and then 50 ml of dilute caustic soda were added
slowly with the usual precautions to the mixture. The organic phase was
separated, dried over anhydrous Na2SO4, the solvent was distilled off and the
residue obtained was distilled under reduced pressure to give 51 g of a thick
oil; boiling point (2 mm Hg), 142°C to 143°C; yield 58%.4th Stage: 10 ml of triethylamine were added in a solution of 25.2 g (0.1
mol) of the amine obtained in the preceding stage in 100 ml of anhydrous
chloroform and the mixture was cooled to 2°C to 3°C. While maintaining this
temperature, 17 g (0.12 mol) of nicotinic acid chloride were added with
vigorous agitation.After evaporation of the solvent, the residue was washed with water, the
product taking the form of a mass. After recrystallization from ethyl acetate, a
constant melting point of 131°C was obtained.
Therapeutic Function
Antihistaminic
Check Digit Verification of cas no
The CAS Registry Mumber 27367-90-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,7,3,6 and 7 respectively; the second part has 2 digits, 9 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 27367-90:
(7*2)+(6*7)+(5*3)+(4*6)+(3*7)+(2*9)+(1*0)=134
134 % 10 = 4
So 27367-90-4 is a valid CAS Registry Number.
InChI:InChI=1/C20H25FN4O/c1-16(23-20(26)17-3-2-9-22-15-17)8-10-24-11-13-25(14-12-24)19-6-4-18(21)5-7-19/h2-7,9,15-16H,8,10-14H2,1H3,(H,23,26)
