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Sigma-Aldrich

10,11-Dihydrocarbamazepine

99%

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Synonym(s):
10,11-Dihydro-5H-dibenz[b,f]azepine-5-carboxamide
Empirical Formula (Hill Notation):
C15H14N2O
CAS Number:
3564-73-6
Molecular Weight:
238.28
EC Number:
222-649-0
MDL number:
MFCD00005072
PubChem Substance ID:
24851693
NACRES:
NA.22

Quality Level

100

Assay

99%

form

solid

mp

205-210 °C (lit.)

solubility

dichloromethane: soluble 2.5%, clear, colorless

SMILES string

NC(=O)N1c2ccccc2CCc3ccccc13

InChI

1S/C15H14N2O/c16-15(18)17-13-7-3-1-5-11(13)9-10-12-6-2-4-8-14(12)17/h1-8H,9-10H2,(H2,16,18)

InChI key

PHNLCHMJDSSPDQ-UHFFFAOYSA-N

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General description

10,11-Dihydrocarbamazepine is an impurity present in dibenzazepine drug used in the treatment of epilepsy. Single-crystal structure of new dimer-based polymorph of 10,11-dihydrocarbamazepine has been investigated.

Application

10,11-Dihydrocarbamazepine was used as internal standard during simultaneous determination of carbamazepine and its active metabolite in plasma by liquid chromatography. It was used in chemiluminescence method for determination of carbamazepine.

Pictograms

Exclamation markHealth hazard
GHS07,GHS08

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Repr. 1A - Skin Sens. 1A - STOT SE 3

Target Organs

Central nervous system

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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A predicted dimer-based polymorph of 10, 11-dihydrocarbamazepine (Form IV).
Arlin J-B, et al.
CrystEngComm, 12(1), 64-66 (2010)
M Eichelbaum et al.
Journal of chromatography, 103(1), 135-140 (1975-01-14)
A liquid-chromatographic method for the simultaneous determination of carbamazepine and its active metabolite (carbamazepine 10,11-epoxide) in plasma has been developed. The two compounds were identified in plasma by mass spectrometry. The lower limit of sensitivity is about 4 and 40
Sang Hak Lee et al.
Analytical sciences : the international journal of the Japan Society for Analytical Chemistry, 19(6), 903-906 (2003-07-02)
A new chemiluminescence method for the determination of carbamazepine (CBZ) has been developed. The method is based on the chemiluminescence produced in the reaction of tris(2,2'-bipyridine)ruthenium(III) and CBZ in an acidic medium. The chemiluminescence intensity was enhanced by organic solvents
William T A Harrison et al.
Acta crystallographica. Section C, Crystal structure communications, 62(Pt 5), o240-o242 (2006-05-09)
The title compound (systematic name: 10,11-dihydro-5H-dibenz[b,f]azepine-5-carboxamide), C15H14N2O, is shown to crystallize as an orthorhombic polymorph to complement the known monoclinic form. The molecular conformations of both forms are very similar, involving a bent conformation for the seven-membered azepine ring and
M G Bixel et al.
European journal of biochemistry, 267(1), 110-120 (1999-12-22)
Several wasp venoms contain philanthotoxins (PhTXs), natural polyamine amides, which act as noncompetitive inhibitors (NCIs) on the nicotinic acetylcholine receptor (nAChR). Effects of varying the structure of PhTXs and poly(methylene tetramine)s on the binding affinity have been investigated. Using the
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