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25523-97-1

25523-97-1 Structure

25523-97-1 Structure
IdentificationBack Directory
[Name]

DEXCHLORPHENIRAMINE
[CAS]

25523-97-1
[Synonyms]

C06946
fortamine
isomerine
phendextro
chlo-amine
Mylaramine
exchlorpheniramine
S-Chlorpheniramine
d-chlorpheniramine
DEXCHLORPHENIRAMINE
(S)-Chloropheniramine
S-(+)-Chlorpheniramine
DEXCHLORPHENIRAMINE BASE
DEXCHLORPHENIRAMINE USP/EP/BP
Dexchlorpheniramine free base
Dexchlorpheniramine (base and/or unspecified salts)
d-2-[p-chloro-alpha-(2-dimethylaminoethyl)benzyl]pyridine
n-dimethyl-gamma-(4-chlorophenyl)-(s)-2-pyridinepropanamin
(S)-γ-(4-Chlorophenyl)-N,N-dimethyl-2-pyridinepropan-1-amine
(+)-2-[(S)-p-Chloro-α-[2-(dimethylamino)ethyl]benzyl]pyridine
2-Pyridinepropanamine, γ-(4-chlorophenyl)-N,N-dimethyl-, (S)-
2-Pyridinepropanamine, γ-(4-chlorophenyl)-N,N-dimethyl-, (γS)-
(3S)-3-(4-chlorophenyl)-N,N-dimethyl-3-pyridin-2-ylpropan-1-amine
(3S)-3-(4-Chlorophenyl)-N,N-dimethyl-3-(2-pyridinyl)-1-propanamine
Pyridine, 2-[p-chloro-α-[2-(dimethylamino)ethyl]benzyl]-, (S)-(+)- (8CI)
[EINECS(EC#)]

247-073-7
[Molecular Formula]

C16H19ClN2
[MDL Number]

MFCD00865695
[MOL File]

25523-97-1.mol
[Molecular Weight]

274.79
Chemical PropertiesBack Directory
[alpha ]

D25 +49.8° (c = 1 in DMF)
[Boiling point ]

142 °C(Press: 1.0 Torr)
[density ]

1.107±0.06 g/cm3(Predicted)
[pka]

9.33±0.28(Predicted)
Safety DataBack Directory
[Hazardous Substances Data]

25523-97-1(Hazardous Substances Data)
Hazard InformationBack Directory
[Originator]

Polaramine,Schering,US,1958
[Uses]

Activity of this drug is approximately twice that of chlorpheniramine. Dexchlorpheniramine is also used for allergy symptoms, rhinitis, and dermatitis.
[Uses]

Antihistaminic.
[Definition]

ChEBI: Dexchlorpheniramine is a chlorphenamine. It is an enantiomer of a levochlorpheniramine.
[Manufacturing Process]

Twenty grams of d-phenylsuccinic acid and 28 grams of 3-(2-pyridyl)-3-pchlorophenyl-N,N-dimethylpropylamine are dissolved in 400 ml of absolute ethyl alcohol and allowed to stand at room temperature until crystallization is effected. The crystals are filtered, washed with absolute ethyl alcohol and recrystallized from 300 ml of this solvent in the same manner. The crystals are recrystallized twice from 80% ethyl alcohol using 3.5 ml per gram of compound in the manner described above and pure d-3-(2-pyridyl)-3-pchlorophenyl-N,Ndimethylpropylamine-d-phenylsuccinate is obtained, melting point 145-147°C.
This salt is shaken with 100 ml of diethyl ether and 50 ml of 20% aqueous potassium carbonate; the ether layer is separated, dried over anhydrous potassium carbonate, filtered and the ether is removed in vacuo. The d-3-(2- pyridyl)-3-p-chlorophenyl-N,N-dimethylpropylamine so obtained is a mobile oil.
4.3 grams of the above base and 1.8 grams of maleic acid are dissolved in 20 ml isopropyl acetate and kept at room temperature until crystallization is complete. The crystals are filtered, washed with ethyl acetate and recrystallized from 15 ml of this solvent in the same manner. The crystalline d-3-(2-pyridyl)-3-p-chlorophenyl-N,N-dimethylpropylamine maleate so formed is then filtered off and dried. MP 113-115°C from US Patent 3,030,371.
[Brand name]

Mylaramine (Morton Grove); Polaramine (Schering).
[Therapeutic Function]

Antihistaminic
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