58955-93-4

Basic information

• Product Name: rac trans-10,11-Dihydro-10,11-dihydroxy Carbamazepine
• Synonyms: (10R,11R)-rel-10,11-Dihydro-10,11-dihydroxy-5H-dibenz[b,f]azepine-5-carbox- amide;Dihydrocarbamazepine-10,11-trans-diol;rac trans-10,11-Dihydro-10,11-dihydroxy Carbamazepine;10,11-trans-dihydroxy-10,11-dihydrocarbamazepine;Rac-trans-10,11-dihydro-10,11- dihydroxycarbazepine-d4;(5S,6S)-5,6-dihydroxy-5,6-dihydrobenzo[b][1]benzazepine-11-carboxamide
• CAS NO: 58955-93-4
• Molecular Formula: C15H14N2O3
• Molecular Weight: 270.287
• Product Categories: Various Metabolites and Impurities;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 58955-93-4.mol
• Article Data: 4

Chemical Properties

• Melting Point: 208-210°C
• Boiling Point: 441.4°C at 760 mmHg
• Flash Point: 220.8°C
• Appearance: /
• Density: 1.443g/cm³
• Vapor Pressure: 1.43E-08mmHg at 25°C
• Refractive Index: 1.711
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated)
• CAS DataBase Reference: rac trans-10,11-Dihydro-10,11-dihydroxy Carbamazepine(CAS DataBase Reference)
• NIST Chemistry Reference: rac trans-10,11-Dihydro-10,11-dihydroxy Carbamazepine(58955-93-4)
• EPA Substance Registry System: rac trans-10,11-Dihydro-10,11-dihydroxy Carbamazepine(58955-93-4)

Safety Data

• Hazardous Substances Data: 58955-93-4(Hazardous Substances Data)

Usage

Chemical Properties

White to Off-White Solid

Uses

Different sources of media describe the Uses of 58955-93-4 differently. You can refer to the following data:
1. A major metabolite of Carbamazepine (C175840).
2. rac trans-10,11-Dihydro-10,11-dihydroxy Carbamazepine is a major metabolite of Carbamazepine (C175840). It can also be used as an anti-epileptic drug and for the removal of micropollutants in municipal wastewaster effluents.

Definition

ChEBI: A dibenzoazepine that is 10,11-dihydro-5H-dibenzo[b,f]azepine-5-carboxamide substituted by hydroxy groups at positions 10 and 11. It is a metabolite of the drug carbamazepine.

InChI:InChI=1/C15H14N2O3/c16-15(20)17-11-7-3-1-5-9(11)13(18)14(19)10-6-2-4-8-12(10)17/h1-8,13-14,18-19H,(H2,16,20)/t13-,14-/m0/s1

Upstream product

• 41359-09-5 1a,10b-dihydro-6H-dibenzooxirenoazepine-6-carbonyl chloride 
• 33948-22-0 5H-dibenz[b,f]azepine-5-carbonylchloride 
• 256-96-2 dibenzoazepine 
• 113952-21-9 5-carbamoyl-10,11-dihydro-11-oxo-5H-dibenzazepine-10-yl acetate 
• 106680-75-5 trans-10,11-dihydro-10,11-dihydroxy-5H-dibenzoazepine-5-carbonyl chloride 
• 298-46-4 carbamazepin 
• 36507-30-9 carbamazepine 10,11-epoxide 

Relevant articles and documents

Carbamazepine oxidation catalyzed by manganese porphyrins: Effects of the β-bromination of the macrocycle and the choice of oxidant

Carbamazepine (CBZ), which is one of the most commonly prescribed antiepileptic drugs and also used in the treatment of trigeminal neuralgia and psychiatric disorders, is metabolized primarily by the cytochromes P450. A homologous series of β-brominated porphyrins derived from 5,10,15,20-tetrakis(4-carbomethoxyphenyl)porphyrinatomanganese(III) chloride, i.e., Mn(III)(BrxTCMPP)Cl (x = 0, 2, 4, 6, and 8), was investigated as cytochrome P450 models for CBZ oxidation in CH2Cl2 by iodosylbenzene, iodobenzene diacetate, tert-butyl hydroperoxide, meta-chloroperoxybenzoic acid, and hydrogen peroxide. Unlike previous studies on metalloporphyrin-based CBZ oxidation, which yielded CBZ epoxide (CBZ-EP) as the sole product, the Mn(III)(BrxTCMPP)Cl systems catalyzed both the oxidation of CBZ to CBZ-EP and the formation of the respective vicinal diol, CBZ-DiOH. The influence of β-bromination of the macrocycle and the choice of the oxidant on the catalytic properties of the Mn(III)(BrxTCMPP)Cl (x = 0, 2, 4, 6, and 8) series were examined. Some partially β-brominated Mn-porphyrins surpass the corresponding octabrominated analogue in efficiency and selectivity, but the extent by which the β-bromination affects the catalytic activity depends on the choice of oxidant. The selectivity for CBZ oxidation to yield the respective epoxide reached 100% or ～94% by using tert-butyl hydroperoxide or hydrogen peroxide as oxygen donors, respectively.

Synthesis of trans-10,11-dihydro-10,11-dihydroxy 5H-dibenz[b,f]azepine-5-carboxamide, a major metabolite of carbamazepine

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