OXOMEMAZINE Chemical Properties

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

Safety Information

Toxicity

LD50 oral in mouse: 140mg/kg

OXOMEMAZINE Usage And Synthesis

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

OXOMEMAZINE(3689-50-7)Related Product Information

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