21186-31-2

Basic information

• Product Name: 2H-Dibenz[b,f]azepin-2-one
• Synonyms: 2H-Dibenz[b,f]azepin-2-one
• CAS NO: 21186-31-2
• Molecular Formula: C₁₄H₉NO
• Molecular Weight: 207.23
• Mol File: 21186-31-2.mol

Chemical Properties

• Boiling Point: 393°C at 760 mmHg
• Flash Point: 162.3°C
• Appearance: /
• Density: 1.18g/cm³
• Vapor Pressure: 2.2E-06mmHg at 25°C
• Refractive Index: 1.646
• CAS DataBase Reference: 2H-Dibenz[b,f]azepin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Dibenz[b,f]azepin-2-one(21186-31-2)
• EPA Substance Registry System: 2H-Dibenz[b,f]azepin-2-one(21186-31-2)

Safety Data

• Hazardous Substances Data: 21186-31-2(Hazardous Substances Data)

Usage

Chemical compound

2H-Dibenz[b,f]azepin-2-one

Also known as

carbazepine

Structure

tricyclic

Classification

anticonvulsant drug

Common uses

treatment of seizures, epilepsy, bipolar disorder

Mechanism of action

stabilizes nerve cells in the brain, reduces abnormal electrical activity to prevent seizures

Other uses

trigeminal neuralgia, alcohol withdrawal syndrome

Efficacy

effective in managing neurological and psychiatric disorders

InChI:InChI=1/C14H9NO/c16-12-7-8-14-11(9-12)6-5-10-3-1-2-4-13(10)15-14/h1-9H

Upstream product

• 256-96-2 dibenzoazepine 

Downstream Products

• 68011-66-5 2-Hydroxycarbamazepine 

Relevant articles and documents

Synthesis of 2,4-Diamino-6-[2′-O-(ω -carboxyalkyl)oxydibenz[b,f]azepin-5-yl]-methylpteridines as Potent and Selective Inhibitors of Pneumocystis carinii, Toxoplasma gondii, and Mycobacterium avium Dihydrofolate Reductase

Six previously undescribed N-(2,4-diaminopteridin-6-yl)methyldibenz[b,f]azepines with water-solubilizing O-carboxyalkyloxy or O-carboxybenzyloxy side chains at the 2′-position were synthesized and compared with trimethoprim (TMP) and piritrexim (PTX) as i

Methods for Treating Cognitive Disorders Using Inhibitors of Histone Deacetylase

This disclosure relates to compounds for the inhibition of histone deacetylase and treatment of a cognitive disorder or deficit. More particularly, the disclosure provides for compounds of formula (I) wherein Q, J, L and Z are as defined in the specification.

Carbamazepine derivatives with P2X4 receptor-blocking activity

Antagonists for the P2 receptor subtype P2X4, an ATP-activated cation channel receptor, have potential as novel drugs for the treatment of neuropathic pain and other inflammatory diseases In the present study, a series of 47 carbamazepine derivatives including 32 novel compounds were designed, synthesized, and evaluated as P2X4 receptor antagonists Their potency to inhibit ATP-induced calcium influx in 1321N1 astrocytoma cells stably transfected with the human P2X4 receptor was determined Additionally, species selectivity (human, rat, mouse) and receptor subtype selectivity (P2X4 vs P2X1, 2, 3, 7) were investigated for selected derivatives The most potent compound of the present series, which exhibited an allosteric mechanism of P2X4 inhibition, was N,N-diisopropyl-5H-dibenz[b,f]azepine-5-carboxamide (34, IC50 of 3.44 μM) The present study extends the so far very limited knowledge on structure-activity relationships of P2X4 receptor antagonists

Detection of 2-hydroxyiminostilbene in the urine of patients taking carbamazepine and its oxidation to a reactive iminoquinone intermediate

Carbamazepine is one of the most widely used anticonvulsants in North America; however, its use is associated with a range of serious idiosyncratic adverse reactions. These reactions are thought to result from the formation of chemically reactive metabolites. Carbamazepine is extensively metabolized in the liver and one of the major metabolites is 2-hydroxycarbamazepine, which has previously been detected as a urinary metabolite excreted by rats and humans along with its further metabolized product, 2- hydroxyiminostilbene. In this study, we found that the urine of patients taking carbamazepine appeared to contain more of the glucuronide of 2- hydroxyiminostilbene than that of 2-hydroxycarbamazepine. We have also demonstrated that 2-hydroxyiminostilbene can be oxidized readily to an iminoquinone species by HOCl, H2O2 or even on exposure to air. The reactivity of this iminoquinone as an electrophile was studied. It was shown to react with sulfhydryl-containing nucleophiles, such as glutathione and N- acetylcysteine. We also found a metabolite with the same molecular weight as 4-methylthio-2-hydroxyiminostilbene, but not the corresponding carbamazepine derivative, in the urine of patients taking carbamazepine and this presumably reflects the formation of a glutathione conjugate of the reactive iminoquinone. This iminoquinone intermediate may play a role in carbamazepine-induced idiosyncratic reactions.

Transformation of Acridines and Azepines into the Corresponding 3-Oxo-heterocycles by Means of Hypervalent Aromatic Iodine Compounds

The acridines 3, 5, and 6, as well as the dibenzoazepine 4 were converted into the 3-oxo-derivatives 7 - 10 using hypervalent iodine compounds (iodosylbenzene and bis-(trifluoroacetoxy)iodopentafluorobenzene).