146-22-5 Usage
Description
Nitrazepam is a 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one, which is substituted at positions 5 and 7 by phenyl and nitro groups, respectively. It is a controlled substance with depressant properties and is known for its anticonvulsant and hypnotic effects. Nitrazepam is a pink solid and is commonly marketed under the brand name Mogadon by Hoffmann LaRoche.
Uses
Used in Pharmaceutical Industry:
Nitrazepam is used as an anticonvulsant for the treatment of epileptic spasms in infants, particularly those suffering from West's syndrome. It helps to control seizures and reduce the frequency of spasms, providing relief to the affected infants.
Nitrazepam is also used as a hypnotic for the short-term management of insomnia. It helps to induce sleep and improve sleep quality in individuals experiencing difficulty falling asleep or staying asleep.
Used in Medical Applications:
As a controlled substance with depressant properties, Nitrazepam is used in the medical field to treat various conditions that require sedation or relaxation. It can be prescribed for patients with anxiety disorders, muscle spasms, or other conditions that may benefit from its calming effects.
Originator
Mogadan,Roche,W. Germany,1965
Manufacturing Process
A mixture of 16.8 g of 2 -aminobenzophenone, 11.9 g of glycine ethyl ester
hydrochloride and 200 cc of pyridine was heated to reflux. After one hour, 20
cc of pyridine was distilled off. The solution was refluxed for 15 hours, then
11.9 g of glycine ethyl ester hydrochloride was added and the refluxing was
continued for an additional 4 hours. The reaction mixture was continued for
an additional 4 hours. The reaction mixture was concentrated in vacuo, then
diluted with ether and water. The reaction product, 5-phenyl-3H-1,4-
benzodiazepin-2(1H)-one, crystallized out, was filtered off, and then
recrystallized from acetone in the form of colorless rhombic prisms, MP 182°C
to 183°C.48 g (0.2 mol) of 5-phenyl-3H-1 ,4-benzodiazepin-2(1 H)-one was dissolved
in 250 cc of concentrated sulfuric acid by stirring at 15°C for ? hour. The
solution was then cooled to 0°C and a mixture of 9.1 cc of fuming nitric acid
(90%, sp. gr. = 1.50) and 11.8 cc of concentrated sulfuric acid was added
dropwise with stirring, keeping the temperature of the reaction mixture
between -5°C and 0°C. After completion of the addition of the nitric acidsulfuric acid mixture, stirring was continued for 1 hour and the reaction
mixture was stored in the refrigerator overnight.The mixture was then added dropwise to 2 kg of crushed ice with stirring and
cooling, keeping the temperature at 0°C. After 1 hour of stirring in the cold,
640 cc of concentrated ammonium hydroxide was added dropwise at 0°C to
pH 8. Stirring was continued for ? hour and the crude product was filtered off, washed with a small amount of ice water and sucked dry overnight. The
crude product was suspended in a mixture of 100 cc of methylene chloride
and 1,700 cc of alcohol. 50 g of decolorizing charcoal was added and the
mixture was refluxed with stirring for 2 hours. After standing overnight at
room temperature 15 g of diatomaceous earth filter aid was added and the
refluxing was resumed for 1? hours. The mixture was filtered while hot. The
clear, light yellow filtrate was concentrated in vacuo on the steam bath with
stirring to about 600 cc. The concentrate was stirred and cooled in ice for
about 2 hours; the precipitated crystalline product was filtered off, washed
with some petroleum ether and sucked dry. The product, 7-nitro-5-phenyl-3H-
1,4-benzodiazepin-2(1H)-one, was recrystallized from a mixture of 1,000 cc of
alcohol and 50 cc of methylene chloride to obtain white prisms melting at
224°C to 225°C.
Therapeutic Function
1,3-Dihydro-7-nitro-5-phenyl-2H-1,4-benzodiazepin-2-one
Clinical Use
Benzodiazepine:
Hypnotic
Safety Profile
Poison by
intraperitoneal and intravenous routes.
Moderately toxic by ingestion. Experimental
reproductive effects. Mutation data
reported. An anticonvulsant and hypnotic
agent. When heated to decomposition it
emits toxic fumes of NOx. See also
DIAZEPAM.
Drug interactions
Potentially hazardous interactions with other drugs
Antibacterials: metabolism possibly increased by
rifampicin.
Antipsychotics: increased sedative effects; risk of
serious adverse effects in combination with clozapine.
Antivirals: concentration possibly increased by
ritonavir.
Disulfiram: metabolism of nitrazepam inhibited,
increased sedative effects.
Sodium oxybate: enhanced effects of sodium oxybate
- avoid
Metabolism
Metabolised in the liver, mainly by nitroreduction
followed by acetylation; none of the metabolites possess
significant activity.
Excreted in the urine mainly as metabolites.
Check Digit Verification of cas no
The CAS Registry Mumber 146-22-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,4 and 6 respectively; the second part has 2 digits, 2 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 146-22:
(5*1)+(4*4)+(3*6)+(2*2)+(1*2)=45
45 % 10 = 5
So 146-22-5 is a valid CAS Registry Number.
InChI:InChI=1/C18H17ClN2O/c1-11(2)16-18(22)20-15-9-8-13(19)10-14(15)17(21-16)12-6-4-3-5-7-12/h3-11,16H,1-2H3,(H,20,22)
146-22-5Relevant articles and documents
Preparation method of nitrazepam
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Paragraph 0008; 0041-0048, (2021/04/07)
The invention discloses a preparation method of nitrazepam, which comprises the following steps: (1) adding 2-chloroacetamido-5-nitro benzophenone, hexamethylenetetramine, ammonium chloride and ethanol into a reaction container, and heating to perform reflux reaction; after the reaction is finished, cooling, adding a protective solvent, adding activated carbon and an adsorbent, stirring for 1 hour while keeping the temperature, filtering, concentrating filtrate under reduced pressure, cooling, filtering, washing with water, and leaching with acetone to obtain a crude product of nitrazepam; and (2) pulping and refining the crude product in a mixed solvent to obtain the nitrazepam. The method is simple in preparation process, low in production cost and suitable for industrial production, the appearance of the finished product can be improved, and the yield is increased by 20%.
Synthesis and Evaluation of Anticonvulsant Activity of Some Schiff Bases of 7-Amino-1,3-dihydro-2H-1,4-benzodiazepin-2-one
Ahamad, Tansir,Dhawale, Kiran,Gawande, Manoj B.,Ghorai, Sujit K.,Nilkanth, Pankaj R.,Sathiyanarayanan, Arulmozhi,Shelke, Sharad N.
, (2020/09/04)
A variety of 1,3-dihydro-2H-1,4-benzodiazepin-2-one azomethines and 1,3-dihydro-2H-1,4-benzodiazepin-2-one benzamide were prepared, characterized and evaluated for the anticonvulsant activity in the rat using picrotoxin-induced seizure model. The prepared 1,3-dihydro-2H-1,4-benzodiazepin-2-one azomethine derivatives emerged potentially anticonvulsant molecular scaffolds exemplified by compounds, 7-{(E)-[(4-nitrophenyl)methylidene]amino}-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one, 7-[(E)-{[4-(dimethylamino)phenyl]methylidene}amino]-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one, 7-{(E)-[(4-bromo-2,6-difluorophenyl)methylidene]amino}-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one and 7-[(E)-{[3-(4-fluorophenyl)-1-phenyl-1H-pyrazol-4-yl]methylidene}amino]-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one. All these four compounds have shown substantial decrease in the wet dog shake numbers and grade of convulsions with respect to the standard drug diazepam. The most active compound, 7-[(E)-{[4-(dimethylamino)phenyl]methylidene}amino]-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one, exhibited 74 % protection against convulsion which was higher than the standard drug diazepam. Furthermore, to identify the binding mode of the interaction amongst the target analogs and binding site of the benzodiazepine receptor, molecular docking study and molecular dynamic simulation were carried out. Additionally, in silico pharmacokinetic and toxicity predictions of target compounds were carried out using AdmetSAR tool. Results of ADMET studies suggest that the pharmacokinetic parameters of all the target compounds were within the acceptable range to become a potential drug candidate as antiepileptic agents.
To improve the octane unleaded light hydrocarbon fuel for vehicle and method for preparing the same
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, (2007/10/05)
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