8-Chloro-5,10-dihydrodibenzo[b,e][1,4]diazepin-11-one
[CAS# 50892-62-1]

Identification

• Classification: Organic raw materials >> Heterocyclic compound
• Name: 8-Chloro-5,10-dihydrodibenzo[b,e][1,4]diazepin-11-one
• Synonyms: 8-Chloro-5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one; 8-Chloro-11-oxo-10,11-dihydro-5H-dibenzo-1,4-diazepine
• Molecular Formula: C₁₃H₉ClN₂O
• Molecular Weight: 244.68
• CAS Registry Number: 50892-62-1
• EC Number: 700-018-5
• SMILES: C1=CC=C2C(=C1)C(=O)NC3=C(N2)C=CC(=C3)Cl

Safety Data

• Hazard Symbols: GHS06;GHS08 Danger
• Risk Statements: H301-H341
• Safety Statements: P203-P264-P270-P280-P301+P316-P318-P321-P330-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H301
Germ cell mutagenicity	Muta.	2	H341
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

8-Chloro-5,10-dihydrodibenzo[b,e][1,4]diazepin-11-one, also known as clorazepate, was first synthesized and identified in the mid-20th century during research into benzodiazepine derivatives. Its discovery stemmed from efforts to develop new psychoactive compounds with anxiolytic and sedative properties. This chemical compound belongs to the benzodiazepine class of drugs, characterized by a diazepine ring fused to two benzene rings. Clorazepate's synthesis and structure were elucidated through organic synthesis techniques and spectroscopic analysis, leading to its characterization as a potent psychoactive agent.

Clorazepate is primarily used as an anxiolytic and sedative medication in the treatment of anxiety disorders and short-term relief of symptoms associated with anxiety. It acts on the central nervous system by enhancing the inhibitory neurotransmitter gamma-aminobutyric acid (GABA), leading to sedative effects and relaxation of muscles. Clorazepate's pharmacological properties make it effective in reducing symptoms of anxiety, tension, and agitation, providing relief to individuals experiencing these conditions.

Clorazepate is also utilized as an anticonvulsant agent in the management of certain types of seizures, including petit mal seizures, akinetic seizures, and myoclonic seizures. Its ability to modulate GABAergic neurotransmission in the brain helps control abnormal electrical activity and prevent seizures from occurring. Clorazepate is often prescribed as adjunctive therapy in combination with other antiepileptic drugs to achieve better seizure control and management of epilepsy.

Clorazepate may be used in the treatment of alcohol withdrawal syndrome due to its calming effects on the central nervous system. It helps alleviate symptoms such as anxiety, agitation, tremors, and insomnia that occur during alcohol withdrawal. By reducing the severity of withdrawal symptoms, clorazepate facilitates the detoxification process and supports individuals in achieving sobriety.

Clorazepate exhibits muscle relaxant properties, making it useful in the management of muscle spasms and skeletal muscle disorders. It acts centrally on the nervous system to reduce muscle tone and inhibit muscle contractions, providing relief from muscle stiffness and discomfort. Clorazepate may be prescribed for conditions such as muscle cramps, spasticity, and dystonia, improving mobility and functional abilities in affected individuals.

In psychiatric practice, clorazepate is sometimes used as adjunctive therapy in the management of depressive disorders, panic attacks, and insomnia. It can complement other psychotropic medications to enhance the therapeutic response and alleviate symptoms associated with these conditions. Clorazepate's anxiolytic and sedative effects contribute to its role in psychiatric treatment, providing relief from distressing symptoms and improving overall quality of life.

References

2020. Reductive Condensation of a Nitro Group with Carboxylic Acids Promoted by Phosphorus(III) Compounds: A Short Route to 5H-Dibenzo[b,e][1,4]diazepin-11(10H)-ones. Synthesis, 52(14).
DOI: 10.1055/s-0040-1707347

2012. A One-Pot Transition-Metal-Free Tandem Process to 1,4-Benzodiazepine Scaffolds. Synthesis, 45(3).
DOI: 10.1055/s-0032-1317781

2007. Design, Synthesis, and Biological Activity of 5,10-Dihydro-dibenzo[b,e][1,4]diazepin-11-one-Based Potent and Selective Chk-1 Inhibitors. Journal of Medicinal Chemistry, 50(15).
DOI: 10.1021/jm070105d