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

Description

Meclonazepam, a benzodiazepine derivative of clonazepam, is a pharmaceutical compound known for its anxiolytic, anticonvulsant, and hypnotic properties. It is characterized by a lower risk of tolerance and dependence development compared to other benzodiazepines, coupled with a longer duration of action, which makes it an advantageous choice for managing chronic conditions such as anxiety disorders and epilepsy.

Uses

Used in Pharmaceutical Industry:
Meclonazepam is used as a sedative and muscle relaxant for its anxiolytic effects, helping to alleviate anxiety and tension in patients.
It is particularly beneficial for individuals suffering from anxiety disorders due to its longer-lasting action and lower risk of dependence.
Used in Neurology:
In the field of neurology, meclonazepam is used as an anticonvulsant to control seizures and other abnormal electrical activity in the brain, making it a valuable treatment for epilepsy and other seizure disorders.
Used in Sleep Aid Industry:
Meclonazepam is utilized as a hypnotic agent to promote sleep and treat insomnia, especially in cases where anxiety or other conditions interfere with the ability to fall asleep or maintain sleep throughout the night.
Used in Chronic Condition Management:
Due to its longer duration of action and lower risk of tolerance, meclonazepam is used as a long-term treatment option for managing chronic conditions that require ongoing sedation and muscle relaxation, such as certain types of muscle spasms or spasticity.

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.