aminometradine Chemical Properties

Melting point:

75-115°; mp 143-144°

Boiling point:

331.89°C (rough estimate)

Density 

1.1985 (rough estimate)

refractive index 

1.5100 (estimate)

Safety Information

Toxicity

LD50 oral in rat: 2300mg/kg

aminometradine Usage And Synthesis

Originator

Mincard,Searle,US,1954

Uses

Mictine is an oral diuretic that is used in the management of edema and in the treatment of congestive heart failure.

Definition

ChEBI: Aminometradine is a pyrimidone.

Manufacturing Process

85 parts of monoallylurea are dissolved in 105 parts of acetic anhydride, and 85 parts of cyanoacetic acid are added gradually and the mixture is maintained at 65°C for 2.5 hours. The mixture is distilled at 20 mm until a syrup remains. 50 parts of water are added to this syrup and distillation is resumed. The resulting syrup is dissolved in 96% ethanol at 60°C, stirred with charcoal and filtered. One to one and one-half volumes of ether are added to the filtrate at 40°C. Upon cooling the N-cyanoacetyl-N'-allylurea precipitates.
It is collected on a filter and washed with ether. The white crystals melt at about 142-143°C. The N-cyanoacetyl-N'-allylurea is dissolved by warming with 10% sodium hydroxide. Sufficient 70% sodium hydroxide is added to raise the pH to 10. The solution is maintained at 60°C for five minutes. After cooling the crystals are collected on a filter and recrystallized from water. 1-Allyl-6- amino-1,2,3,4-tetrahydro-2,4-pyrimidinedione is obtained in the form of white crystals melting at 270-272°C.
334 parts of 1-allyl-6-amino-1,2,3,4-tetrahydro-2,4-pyrirnidinedione are dissolved in a solution of 88 parts of sodium hydroxide in 1,100 parts of water. While this mixture is stirred rapidly at 50°C, 430 parts of diethyl sulfate are added in the course of 30 minutes. Stirring is continued at 50-55°C for one hour longer, and an alkaline reaction is maintained by occasional additions of small portions of 20% aqueous sodium hydroxide solution, about 300 parts in all being required. On cooling, the 1-allyl-3-ethyl-6-amino-1,2,3,4- tetrahydro-2,4-pyrimidinedione separates as the monohydrate; it is filtered off, washed with cold water, and recrystallized from water containing a small amount of sodium hydroxide to hold in solution any unreacted 1-allyl-6- amino-1,2,3,4-tetrahydro-2,4-pyrimidinedione. The air dried product thus obtained contains 1 mol of crystal water and melts over a wide range with dehydration at 75-115°C. After dehydration by treatment with anhydrous ether, the anhydrous 1-allyl-3-ethyl-6-amino-1,2,3,4-tetrahydro-2,4- pyrimidinedione melts sharply at about 143-144°C.

Therapeutic Function

Diuretic

aminometradine(642-44-4)Related Product Information

• Fluazinam
• Triamterene
• 1,3-Dimethyluracil
• 6-Amino-3-methyluracil
• 6-AMINO-1-ETHYL-1H-PYRIMIDINE-2,4-DIONE
• 6-Amino-1-methyluracil
• 6-Amino-1,3-dimethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
• 2(1H)-Pyrimidinone,4-amino-3,6-dihydro-1-methyl-
• 1-ALLYLPYRIMIDINE-2,4(1H,3H)-DIONE
• 1,3-DIETHYL-6-AMINOURACIL
• aminometradine
• 1,3-DIALLYLUREA