ChemicalBook--->CAS DataBase List--->3689-50-7

3689-50-7

3689-50-7 Structure

3689-50-7 Structure
IdentificationBack Directory
[Name]

OXOMEMAZINE
[CAS]

3689-50-7
[Synonyms]

Imakol
RP-6847
6487 RP
6847 RP
Dysedon
Dosegran
Doxergan
6847 R.P.
Oxomemazin
OXOEMAZINE
Oxomenazine
Oxymemazine
OXOMEMAZINE
Oxomemazinebase
Alimemazine S,S-dioxide
Trimeprazine 5,5-dioxide
3-(5,5-dioxophenothiazin-10-yl)-N,N,2-trimethylpropan-1-amine
3-(5,5-dioxophenothiazin-10-yl)-N,N,2-trimethyl-propan-1-amine
10-(3-(Dimethylamino)-2-methylpropyl)phenothiazine-5,5-dioxide
10H-Phenothiazine-10-propanamine, N,N,β-trimethyl-, 5,5-dioxide
N,N,β-Trimethyl-10H-phenothiazine-10-propan-1-amine 5,5-dioxide
10-[2-(Dimethylaminomethyl)propyl]-10H-phenothiazine 5,5-dioxide
S,S-Dioxo-9,9-(dimethylamino-3-methyl-2-propyl)-10-phenothiazine
[3-(5,5-diketophenothiazin-10-yl)-2-methyl-propyl]-dimethyl-amine
10-(3-Dimethylamino-2-methylpropyl)-10H-phenothiazine 5,5-dioxide
Phenothiazine, 10-[3-(dimethylamino)-2-methylpropyl]-, 5,5-dioxide
10H-Phenothiazine-10-propanamine, N,N,beta-trimethyl-, 5,5-dioxide
3-(5,5-Dioxido-10H-phenothiazin-10-yl)-N,N,2-trimethyl-1-propanamine
[EINECS(EC#)]

222-996-8
[Molecular Formula]

C18H22N2O2S
[MDL Number]

MFCD00868197
[MOL File]

3689-50-7.mol
[Molecular Weight]

330.44
Chemical PropertiesBack Directory
[Melting point ]

115°
[Boiling point ]

492.4±34.0 °C(Predicted)
[density ]

1.1453 (rough estimate)
[refractive index ]

1.6000 (estimate)
[storage temp. ]

Store at -20°C
[solubility ]

≥ 33mg/mL in DMSO
[form ]

Solid
[pka]

9.31±0.28(Predicted)
[color ]

White to off-white
[InChI]

InChI=1S/C18H22N2O2S/c1-14(12-19(2)3)13-20-15-8-4-6-10-17(15)23(21,22)18-11-7-5-9-16(18)20/h4-11,14H,12-13H2,1-3H3
[InChIKey]

QTQPVLDZQVPLGV-UHFFFAOYSA-N
[SMILES]

N1(CC(C)CN(C)C)C2C=CC=CC=2S(=O)(=O)C2C=CC=CC1=2
Hazard InformationBack Directory
[Originator]

Doxergan,Specia,France,1964
[Uses]

(±)-Oxomemazine, is a phenothiazine-type antihistamines, that has also shown antibacterial activity against Mycobacterium tuberculosis.
[Definition]

ChEBI: Oxomemazine is a member of phenothiazines.
[Manufacturing Process]

Phenothiazine is reacted with 3-dimethylamino-2-methylpropyl chloride in the presence of sodium amide to give 3-(10-phenthiazinyl)-2-methyl-1dimethylaminopropane. 11.9 g of of this intermediate is dissolved with agitation in glacial acetic acid (120 cc). Pure sulfuric acid (d = 1.83; 0.5 cc) is added and a mixture of glacial acetic acid (10 cc) and hydrogen peroxide (8.5 cc of a solution containing 38 g of hydrogen peroxide in 100 cc) is then run in over 20 minutes. The temperature rises from 25°C to 35°C and is then kept at 60°C for 18 hours. The mixture is cooled and water (150 cc) is added and, with cooling, aqueous sodium hydroxide (d = 1.33; 220 cc). The resulting mixture is extracted with ethyl acetate (3 x 100 cc), the solvent is evaporated on a water bath and the residue is recrystallized from heptane (150 cc). 3(9,9-dioxy-10-phenthiazinyl)-2-methyl-1-dimethylaminopropane (78 g) is obtained, MP 115°C.
The corresponding hydrochloride prepared in ethyl acetate and recrystallized from a mixture of ethanol and isopropanol melts at 250°C.
[Therapeutic Function]

Antihistaminic
[storage]

Store at -20°C
Safety DataBack Directory
[Toxicity]

LD50 oral in mouse: 140mg/kg
Spectrum DetailBack Directory
[Spectrum Detail]

OXOMEMAZINE(3689-50-7)1HNMR
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