2886-65-9

Basic information

• Product Name: 7-Chloro-5-(2-fluoro-phenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one
• Synonyms: cm7116;DESALKYLFLURAZEPAM,100/MLINMETHANOL;nor-Flurazepam;Flurazepam Related Compound F (50 mg) (7-chloro-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one);7-Chloro-5-(2-fluorophenyl)-1H-benzo[e][1,4]diazepin-2(3H)-one;FlurazepaM Related CoMpound F;7-chloro-5-(2-fluorophenyl)- 1,4-Benzodiazepin-2-one;desalkylflurazepam Solution, 100ppm
• CAS NO: 2886-65-9
• Molecular Formula: C₁₅H₁₀ClFN₂O
• Molecular Weight: 288.7
• EINECS: 220-748-3
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;pharmacetical;(intermediate of fludiazepam,flurazepam);Aromatics;Heterocycles;medical intermediate
• Mol File: 2886-65-9.mol
• Article Data: 11

Chemical Properties

• Melting Point: 204-206°C
• Boiling Point: 454 °C at 760 mmHg
• Flash Point: 9℃
• Appearance: Light yellow solid
• Density: 1.39 g/cm³
• Vapor Pressure: 1.97E-08mmHg at 25°C
• Refractive Index: 1.647
• Storage Temp.: -20°C Freezer
• PKA: 11.55±0.70(Predicted)
• CAS DataBase Reference: 7-Chloro-5-(2-fluoro-phenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Chloro-5-(2-fluoro-phenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one(2886-65-9)
• EPA Substance Registry System: 7-Chloro-5-(2-fluoro-phenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one(2886-65-9)

Safety Data

• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 22-24/25-45-36/37-16-7
• RIDADR: UN1230 - class 3 - PG 2 - Methanol, solution
• WGK Germany: 2
• RTECS: DF2370100
• Hazardous Substances Data: 2886-65-9(Hazardous Substances Data)

Usage

Description

Desalkylflurazepam (Item No. 18484) is an analytical reference material that is structurally categorized as a benzodiazepine. It is an active metabolite of several benzodiazepines, including flurazepam , flutoprazepam, fludiazepam, midazolam, and quazepam. Desalkylflurazepam inhibits L-type voltage-gated calcium channels (Cav; IC50s = 55 and 37 μM for Cav1.2 and 1.3, respectively) by positively modulating GABAA receptors. It can be detected in urine, serum, and meconium by LC-MS/MS. This product is intended for research and forensic applications.

Chemical Properties

Light Yellow Solid

Uses

The major human metabolite of flurazepam. This is a controlled drug precursor therefore a liscence may be required for purchase

Mode of action

N-Desalkylflurazepam is a benzodiazepine analog and an active metabolite of several other benzodiazepine drugs including flurazepam, flutoprazepam, fludiazepam, midazolam, flutazolam, quazepam, and ethyl loflazepate. It is long-acting, prone to accumulation, and binds unselectively to the various benzodiazepine receptor subtypes. It has been sold as a designer drug from 2016 onward.

InChI:InChI=1/C15H10ClFN2O/c16-9-5-6-13-11(7-9)15(18-8-14(20)19-13)10-3-1-2-4-12(10)17/h1-7H,8H2,(H,19,20)

Upstream product

• 100-97-0 hexamethylenetetramine 
• 2836-40-0 2-(2-chloroacetyl)amino-4-chloro-2'-fluorobenzophenone 
• 1350621-36-1 C₂₀H₂₀ClFN₂O₄ 
• 4530-20-5 BOC-glycine 
• 784-38-3 2-amino-5-chloro-2'-fluorobenzophenone 
• 76488-35-2 7-chloro-5-(2-fluorophenyl)-N-hydroxy-alpha-nitro-3H-1,4-benzodiazepine-2-methanimine 
• 393-52-2 2-Fluorobenzoyl chloride 
• 106-47-8 4-chloro-aniline 
• 1584-62-9 2?(2?bromoacetamido)?5?chloro?2'?fluorobenzophenone 
• 17617-23-1 flurazepam 
• 76488-08-9 7-chloro-5-(2-fluorophenyl)-N-methoxy-alpha-nitro-3H-1,4-benzodiazepine-2-methanimine 
• 59467-63-9 7-chloro-5-(2-fluorophenyl)-2-nitromethylene-1,3-dihydro-2H-1,4-benzodiazepine 
• 1172-18-5 flurazepam dihydrochloride 

Downstream Products

• 28910-91-0 flualprazolam 
• 59467-61-7 7-chloro-5-(2-fluorophenyl)-3H-1,4-benzodiazepine-2-methylamine 
• 1355498-53-1 C₁₈H₁₄ClFN₂O₃ 
• 1350644-52-8 7-chloro-1,3-dihydro-1-ferrocenylmethyl-5-(2-fluorophenyl)-2H-1,4-benzodiazepin-2-one 
• 27090-93-3 7-Chloro-8b-(2-fluoro-phenyl)-4,8b-dihydro-1-oxa-1a,4-diaza-benzo[a]cyclopropa[c]cyclohepten-3-one 
• 19011-80-4 3-acetoxy-7-chloro-5-(2-fluoro-phenyl)-1,3-dihydro-benzo[e][1,4]diazepin-2-one 
• 69585-93-9 ethyl 8?chloro?6?(2?fluorophenyl)?4H?imidazo[1,5?a][1,4]benzodiazepine?3?carboxylate 
• 52829-30-8 7-chloro-1-(2,3-dihydroxy-propyl)-5-(2-fluoro-phenyl)-1,3-dihydro-benzo[e][1,4]diazepin-2-one 
• 24143-22-4 10-chloro-11b-(2-fluoro-phenyl)-2,3,7,11b-tetrahydro-benzo[f]oxazolo[3,2-d][1,4]diazepin-6-one 
• 52829-41-1 1-allyl-7-chloro-5-(2-fluoro-phenyl)-4-oxy-1,3-dihydro-benzo[e][1,4]diazepin-2-one 
• 59688-88-9 di-morpholin-4-yl-phosphinic acid 7-chloro-5-(2-fluoro-phenyl)-3H-benzo[e][1,4]diazepin-2-yl ester 

Relevant articles and documents

Improved and scalable methods for the synthesis of midazolam drug and its analogues using isocyanide reagents

Abstract: In this research, two improved and scalable methods for the synthesis of midazolam and its analogues have been described. Midazolam has been synthesized using isocyanide reagents in satisfactory yield. In this methodology, imidazobenzodiazepine intermediates can be easily prepared via an improved process. One-pot condensation of benzodiazepines with mono-anion of tosylmethyl isocyanide or ethyl isocyanoacetate under mild condition led to formation of imidazobenzodiazepine. In the first method, tosylmethyl isocyanide (Tos-MIC) is used and the number of synthetic steps are decreased in comparison to previous report. In the second method, ethyl isocyanoacetate which is commonly used for the synthesis of some imidazobenzodiazepines, is consumed to generate midazolam. The latter, a relatively different method for the synthesis of midazolam analogues has been reported. Graphical abstract: [Figure not available: see fulltext.].

Synthesis and in vitro anti-hepatitis B virus activities of 4-aryl-6-chloro-quinolin-2-one and 5-aryl-7-chloro-1,4-benzodiazepine derivatives

A series of 4-aryl-6-chloro-quinolin-2-ones and 5-aryl-7-chloro-1,4-benzodiazepine were synthesized and assayed for their in vitro anti-hepatitis B virus activities and cytotoxicities for the first time. Some of the tested compounds were active against HBsAg and HBeAg secretion in Hep G2.2.15 cells. Compound 5c showed IC50 of 0.074 and 0.449 mM on HBsAg and HBeAg secretions, respectively, which were 10 times higher than that of its analog 4c and led to better selective index (SI) values (SI = 23.2 and 3.4, respectively).

Novel benzo[1,4]diazepin-2-one derivatives as endothelin receptor antagonists

Since its discovery in 1988 by Yanagisawa et al., endothelin (ET), a potent vasoconstrictor, has been widely implicated in the pathophysiology of cardiovascular, cerebrovascular, and renal diseases. Many research groups have embarked on the discovery and development of ET receptor antagonists for the treatment of such diseases. While several compounds, e.g., ambrisentan 2, are in late clinical trials for various indications, one compound (bosentan, Tracleer) is being marketed to treat pulmonary arterial hypertension. Inspired by the structure of ambrisentan 2, we designed a novel class of ET receptor antagonists based on a 1,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-2-one scaffold. Here, we report on the preparation as well as the in vitro and in vivo structure-activity relationships of these derivatives. Potent dual ET A/ETB receptor antagonists with affinities in the low nanomolar range have been identified. In addition, several compounds efficiently reduced arterial blood pressure after oral administration to Dahl salt sensitive rats. In this animal model, the efficacy of the benzo[e] [1,4]diazepin-2-one derivative rac-39au was superior to that of racemic ambrisentan, rac-2.