10,11-Dihydrocarbamazepine

Names

[ Name ]:
10,11-Dihydrocarbamazepine

[Synonym ]:
10,11-dihydro-5-carboxamido-5H-dibenz<b,f>azepine
10,11-Dihydro-5-carbamoyl-5H-dibenz<b,f>azepin
10,11-Dihydro-5-carbamoyl-5H-dibenz<b,f>azepine
GP 26-301
10,11-DIHYDROCARBAMAZEPINE
EINECS 222-649-0
10,11-Dihydro-5H-dibenz[b,f]azepine-5-carboxamide
10,11-Dihydrocarbamazepine,10,11-Dihydro-5H-dibenz[b,f]azepine-5-carboxamide
MFCD00005072
10,11-Dihydro-5H-dibenz(b,f)azepine-5-carboxamide
10,11-Dihydro-5H-dibenzo[b,f]azepine-5-carboxamide
5H-DIBENZ(b,f)AZEPINE-5-CARBOXAMIDE,10,11-DIHYDRO
5H-Dibenz[b,f]azepine-5-carboxamide, 10,11-dihydro-

Biological Activity

[Description]:

10,11-Dihydrocarbamazepine is the active metabolite of Oxcarbazepine. 10,11-Dihydrocarbamazepine also is an intermediate. Oxcarbazepine is rapidly and almost completely converted to 10,11-Dihydrocarbamazepine with probable Anticonvulsant efficacy[1].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Neurological Disease

[In Vitro]

Oxcarbazepine is metabolized in the liver to its active metabolite, 10,11-Dihydrocarbamazepine. Oxcarbazepine is an antiepileptic drug (AED) used to treat partial seizures as a monotherapy or adjunctive therapy[1]. 10,11-Dihydrocarbamazepine may be used as a reference standard for the determination of 10,11-dihydrocarbamazepine in pharmaceutical formulations by liquid chromatography (LC)[1].

[References]

[1]. Courtney Hunek, et al. Measurement of 10,11-dihydro-10-hydroxy-carbamazepine in serum and plasma by high-performance liquid chromatography. Clin Chem Lab Med. 2008;46(10):1429-33.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
394.5±52.0 °C at 760 mmHg

[ Melting Point ]:
205-210ºC

[ Molecular Formula ]:
C₁₅H₁₄N₂O

[ Molecular Weight ]:
238.28

[ Flash Point ]:
192.4±30.7 °C

[ Exact Mass ]:
238.110611

[ PSA ]:
46.33000

[ LogP ]:
2.60

[ Vapour Pressure ]:
0.0±0.9 mmHg at 25°C

[ Index of Refraction ]:
1.645

[ Storage condition ]:
Refrigerator

[ Water Solubility ]:
dichloromethane: soluble2.5%, clear, colorless | Soluble in dichloromethane. Insoluble in water.

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: HN8300000

CHEMICAL NAME :: 5H-Dibenz(b,f)azepine-5-carboxamide, 10,11-dihydro-

CAS REGISTRY NUMBER :: 3564-73-6

BEILSTEIN REFERENCE NO. :: 0196969

LAST UPDATED :: 199712

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C15-H14-N2-O

MOLECULAR WEIGHT :: 238.31

WISWESSER LINE NOTATION :: T C676 BN&T&J BVZ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 750 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 7,88,1964

Safety Information

[ Symbol ]:

GHS07, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H302-H317-H334

[ Precautionary Statements ]:
P261-P280-P342 + P311

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
22-42/43

[ Safety Phrases ]:
S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
HN8300000

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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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 str...

Liquid chromatographic methods for assay of carbamazepine, 10,11-dihydrocarbamazepine, and related compounds in carbamazepine drug substance and tablets.

J. Assoc. Off. Anal. Chem. 70(5) , 836-40, (1987)

Liquid chromatographic (LC) methods have been developed for the determination of carbamazepine, the impurity 10,11-dihydrocarbamazepine, and related compounds in carbamazepine drug substance and table...

An orthorhombic polymorph of 10,11-dihydrocarbamazepine.

Acta Crystallogr. C 62(Pt 5) , o240-2, (2006)

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 mo...