67027-56-9

Basic information

• Product Name: meclonazepam
• Synonyms: Meclonazepam;5-(2-Chlorophenyl)-1,3-dihydro-3-methyl-7-nitro-2H-1,4-benzodiazepin-2-one;(RS)-Ro 11-3128/002;2H-1,4-Benzodiazepin-2-one, 5-(2-chlorophenyl)-1,3-dihydro-3-methyl-7-nitro-;Ro 11-3128/002;67027-56-9
• CAS NO: 67027-56-9
• Molecular Formula: C₁₆H₁₂ClN₃O₃
• Molecular Weight: 329.73778
• Mol File: 67027-56-9.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 522.1°Cat760mmHg
• Flash Point: 269.6°C
• Appearance: /
• Density: 1.46g/cm³
• Vapor Pressure: 5.34E-11mmHg at 25°C
• Refractive Index: 1.686
• CAS DataBase Reference: meclonazepam(CAS DataBase Reference)
• NIST Chemistry Reference: meclonazepam(67027-56-9)
• EPA Substance Registry System: meclonazepam(67027-56-9)

Safety Data

• Hazardous Substances Data: 67027-56-9(Hazardous Substances Data)

Usage

General Description

Meclonazepam is a chemical compound belonging to the class of benzodiazepine drugs, which are commonly used as sedatives and muscle relaxants. It is a derivative of clonazepam with similar properties, including anxiolytic, anticonvulsant, and hypnotic effects. Meclonazepam is reported to have a lower risk of developing tolerance and dependence compared to other benzodiazepines, and it has a longer duration of action, making it suitable for treating chronic conditions such as anxiety disorders and epilepsy. However, it is important to note that meclonazepam is a controlled substance and should be used under strict medical supervision to prevent potential misuse and addiction.

InChI:InChI=1/C16H12ClN3O3/c1-9-16(21)19-14-7-6-10(20(22)23)8-12(14)15(18-9)11-4-2-3-5-13(11)17/h2-9H,1H3,(H,19,21)

Synthetic route

(+)-5-(o-chlorophenyl)-1,3-dihydro-3-methyl-7-nitro-2H-1,4-benzodiazepin-2-one (67027-56-9) → C16H14ClN3O3 (1028633-79-5)

Conditions	Yield
With sodium cyanoborohydride; acetic acid In tetrahydrofuran	90%

(+)-5-(o-chlorophenyl)-1,3-dihydro-3-methyl-7-nitro-2H-1,4-benzodiazepin-2-one (67027-56-9) → C16H14ClN3O (1028633-52-4)

Conditions	Yield
With hydrogenchloride; tin In ethanol Heating;	50%

(+)-5-(o-chlorophenyl)-1,3-dihydro-3-methyl-7-nitro-2H-1,4-benzodiazepin-2-one (67027-56-9) → 5-(2-chloro-phenyl)-3-methyl-7-nitro-1,3-dihydro-benzo[e][1,4]diazepine-2-thione (59937-50-7)

Conditions	Yield
With Lawessons reagent In tetrahydrofuran	10%
With diphosphorus pentasulfide; triethylamine In 1,4-dioxane; dichloromethane; ethyl acetate

(+)-5-(o-chlorophenyl)-1,3-dihydro-3-methyl-7-nitro-2H-1,4-benzodiazepin-2-one (67027-56-9) + methyl iodide (74-88-4) → (+)-5-(o-chlorophenyl)-1,3-dihydro-1,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one

Conditions	Yield
With potassium carbonate In ethanol; dichloromethane; acetone

Downstream Products

• 1028633-52-4 C₁₆H₁₄ClN₃O 
• 1028633-79-5 C₁₆H₁₄ClN₃O₃ 
• 59937-50-7 5-(2-chloro-phenyl)-3-methyl-7-nitro-1,3-dihydro-benzo[e][1,4]diazepine-2-thione 

Relevant articles and documents

Benzodiazepine derivatives

This invention is directed toward pharmacologically active compounds of the formula STR1 wherein R represents a hydrogen atom or a lower alkyl group and R1 represents a hydrogen or halogen atom or a trifluoromethyl group which have the absolute configuration S at the 3-position carbon atom. Also presented is a process to produce the above benzodiazepine derivatives and pharmaceutical preparations therefor. The above benzodiazepine derivatives exhibit pronounced anthelmintic, especially schistosomicidal, activity and muscle relaxant, anticonvulsant and sedative activities.