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3978-86-7

3978-86-7 Structure

3978-86-7 Structure
IdentificationBack Directory
[Name]

AZATADINE MALEATE (200 MG)
[CAS]

3978-86-7
[Synonyms]

Zadine
idulian
optimine
sch10649
idinedimaleate
Einecs 223-615-8
azatadinemaleate
azatadinedimaleate
AZATADINE MALEATE (200 MG)
AZATADINE MALEATE USP/EP/BP
AZATADINE MALEATE;OPTIMINE;ZADINE
AZATADINE MALEATE (200 MG) USP/EP/BP
Azatadine Maleate(Azatadine dimaleate)
6,11-dihydro-11-(1-methyl-4-piperidylidene)5h-benzo(5,6)cyclohepta(1,2-b)pyr
11h-benzo(5,6)cyclohepta(1,2-b)pyridine,5,6-dihydro-11-(1-methyl-4-piperidylid
6,11-Dihydro-11-(1-methyl-4-piperidylidene)5H-benzo(5,6)cyclohepta(1,2-B)pyridine dimaleate
6,11-dihydro-11-(1-methylpiperidin-4-ylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine dimaleate
11H-Benzo(5,6)cyclohepta(1,2-B)pyridine, 5,6-dihydro-11-(1-methyl-4-piperidylidene)-, dimaleate
5H-Benzo(5,6)cyclohepta(1,2-B)pyridine, 6,11-dihydro-11-(1-methyl-4-piperidinylidene)-, (Z)-2-butenedioate (1:2)
5H-Benzo[5,6]cyclohepta[1,2-b]pyridine, 6,11-dihydro-11-(1-methyl-4-piperidinylidene)-, (2Z)-2-butenedioate (1:2)
[EINECS(EC#)]

223-615-8
[Molecular Formula]

C28H30N2O8
[MDL Number]

MFCD00242593
[MOL File]

3978-86-7.mol
[Molecular Weight]

522.546
Chemical PropertiesBack Directory
[Melting point ]

152-154°
[storage temp. ]

Sealed in dry,Room Temperature
[solubility ]

DMSO (Slightly), Methanol (Slightly)
[form ]

Solid
[color ]

White to Off-White
Safety DataBack Directory
[HS Code ]

2933399090
Hazard InformationBack Directory
[Chemical Properties]

White Solid
[Originator]

Idulian,Unilabo,France,1968
[Uses]

Antihistaminic.
[Definition]

ChEBI: The dimaleate salt of azatadine.
[Manufacturing Process]

Preparation of 4-aza-5-(N-methyl-4-piperidyl)-10,11-dihydro-5Hdibenzo[ a,d]cycloheptene-5-ol: Add 17.4 g of N-methyl-4-chloropiperidine to a stirred mixture containing 3.2 g of magnesium, 20 ml of anhydrous tetrahydrofuran, 1 ml of ethyl bromide and a crystal of iodine. Reflux for two hours, cool to 30-35°C and add a solution of 13 g of 4-aza-10,11-dihydro-5Hdibenzo[ a,d]cycloheptene-5-one in 25 ml of tetrahydrofuran. Stir for five hours, remove the solvent by distillation in vacuum and add 250 ml of ether. Add 100 ml of 10% ammonium chloride solution and extract the mixture with chloroform. Concentrate the chloroform solution to a residue and recrystallize from isopropyl ether obtaining 20 g of the carbinol, MP 173-174°C.
Preparation of 4-aza-5-(N-methyl-4-piperidylidene)-10,11-dihydro-5Hdibenzo[ a,d]cycloheptene: Heat 5.4 g of the carbinol and 270 g of polyphosphoric acid for 12 hours at 140-170°C. Pour into ice water and make alkaline with sodium hydroxide. Extract with ether. Dry ether solution and concentrate to a residue. Crystallize from isopropyl ether, MP 124-126°C.
Preparation of 4-aza-5-(N-methyl-4-piperidylidene)-10,11-dihydro-5Hdibenzo[ a,d]cycloheptene dimaleate: To a solution containing 4.3 g of 4-aza- (N-methyl-4-piperidylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene in 55 ml of ethyl acetate, add a solution of 3.45 g of maleic acid dissolved in ethyl acetate. Filter the resulting precipitate and recrystallize the desired product from an ethyl acetate-methanol mixture to yield 4-aza-5-(N-methyl-4- piperidylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene dimaleate, MP 152-154°C.
[Brand name]

Optimine (Schering);Verban.
[Therapeutic Function]

Antihistaminic
[General Description]

Azatadine maleate, 6,11-dihydro-11-(l-methyl-4-piperidylidene)-5H-benzo-[5,6]cyclo-hepta(1,2-b]pyridine maleate (1:2) (Optimine), is a potent,long-acting antihistaminic with antiserotonin activity. Inearly testing, azatadine exhibited more than three times thepotency of chiorpheniramine in the isolated guinea pigileum screen and more than seven times the oral potency ofchlorpheniramine in protection of guinea pigs against a doublelethal dose of intravenously administered histamine.
[storage]

Store at -20°C
Spectrum DetailBack Directory
[Spectrum Detail]

AZATADINE MALEATE (200 MG)(3978-86-7)1HNMR
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