Nitrazepam

Base Information

• Chemical Name: Nitrazepam
• CAS No.: 146-22-5
• Molecular Formula: C15H11N3O3
• Molecular Weight: 281.271
• European Community (EC) Number: 205-665-2
• NSC Number: 58775
• UNII: 9CLV70W7HS
• DSSTox Substance ID: DTXSID5023372
• Nikkaji Number: J2.956D
• Wikipedia: Nitrazepam
• Wikidata: Q410078
• NCI Thesaurus Code: C87674
• Pharos Ligand ID: JP8537M7ATPV
• Metabolomics Workbench ID: 43583
• ChEMBL ID: CHEMBL13209
• Mol file: 146-22-5.mol

Synonyms:Alodorm;Dormalon;Dormo-Puren;Eatan;Imadorm;imeson;Mogadon;Nitrazadon;Nitrazep;Nitrazepam;Nitrazepam AL;Nitrazepam Neuraxpharm;Nitrazepam-neuraxpharm;Nitrodiazepam;Novanox;Radedorm;Remnos;Rhoxal Nitrazepam;Rhoxal-nitrazepam;Serenade;Somnite

 This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.

Chemical Property of Nitrazepam

Chemical Property:

• Appearance/Colour: Pink Solid
• Vapor Pressure: 6.33E-09mmHg at 25°C
• Melting Point: 226-229 ºC
• Refractive Index: 1.627
• Boiling Point: 497 ºC at 760 mmHg
• PKA: pKa 2.90 ± 0.05;10.39±0.04(H2O,t =25,I=0.015(KCl))(Approximate)
• Flash Point: 254.4 ºC
• PSA: 87.28000
• Density: 1.4 g/cm³
• LogP: 2.48110
• Storage Temp.: Controlled Substance, -20°C Freezer
• Solubility.: Practically insoluble in water, slightly soluble in ethanol (96 per cent).
• Water Solubility.: 3.93mg/L(25 oC)
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 281.08004122
• Heavy Atom Count: 21
• Complexity: 452

Purity/Quality:

Safty Information:

• Hazard Codes: Xn,F
• Statements: 22-36-20/21/22-11
• Safety Statements: 36/37/39-36/37-16

MSDS Files:

Useful:

• Canonical SMILES: C1C(=O)NC2=C(C=C(C=C2)[N+](=O)[O-])C(=N1)C3=CC=CC=C3
• Recent ClinicalTrials: Pharmacovigilance in Gerontopsychiatric Patients
• Recent EU Clinical Trials: Self-help program for hypnotics withdrawal in insomniac patients: A randomized controlled clinical trial.
• Uses: Anticonvulsant; hypnotic. Controlled substance (depressant)
• Therapeutic Function: 1,3-Dihydro-7-nitro-5-phenyl-2H-1,4-benzodiazepin-2-one
• Clinical Use: Benzodiazepine: Hypnotic
• 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

Technology Process of Nitrazepam

There total 13 articles about Nitrazepam which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

2,3-dihydro-5-phenyl-1H-1,4-benzodiazepin-2-one (2898-08-0) → nitrazepam (146-22-5)

Guidance literature:

With 3-(ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium bis(trifluoromethanesulfonyl)imide; at 20 ℃; for 5h; Ionic liquid;

DOI:10.1016/j.tetlet.2019.151529

Reference yield: 86.0%

(C6H3NO2)NCOCH2NC(C6H5)AuP(C6H5)3 (128493-73-2) + para-thiocresol (106-45-6) → triphenylphosphine p-toluenethiolate gold(I) complex (121860-53-5) + nitrazepam (146-22-5)

Guidance literature:

In methanol; stirring of a soln. of thiol and Au-compd. in MeOH for 1 h at room temp.; evapn. to dryness, dissolving of residue with diethyl ether gives ligand(IR, mp), evapn. of ether soln. to dryness, dissolving of residue in CHCl3, addn. of hexane, elem. anal.;

DOI:10.1016/S0020-1693(00)88014-7

Reference yield: 85.0%

N,N'-methylenebis<3-(2'-benzoyl-4-nitro)phenyl>-4-imidazolidin (76895-82-4) → nitrazepam (146-22-5)

Guidance literature:

With ammonium chloride; In ethanol; Heating;

DOI:10.1002/jhet.5570180523

upstream raw materials:

N,N'-methylenebis<3-(2'-benzoyl-4-nitro)phenyl>-4-imidazolidin

2-aminomethyl-3-phenyl-5-nitroindole

hexamethylenetetramine

N-(2-benzoyl-4-nitrophenyl)-2-chloroacetamide

Downstream raw materials:

1-methoxymethyl-7-nitro-5-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one

7-dimethylamino-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepine

2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-7-carbonitrile

7-hydroxyamino-5-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one

Refernces

• 1、 Saito, Koichi,Yokota, Mai,Saito, Sachi,Ito, Rie. "Elucidation of degradation behavior of nitrazepam and other benzodiazepines in artificial gastric juice: Study on degradability of drugs in stomach (II)". . p. 258 - 264. Retrieved 2021/03/08.
• 2、 Chaudhary, Renu,Natarajan, Palani,Rani, Neetu,Sakshi,Venugopalan, Paloth. "3-(Ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium cation: A green alternative to tert-butyl nitrite for synthesis of nitro-group-containing arenes and drugs at room temperature". supporting information. . Retrieved 2019/12/30.