amisometradine Chemical Properties

Melting point:

175°

Boiling point:

331.89°C (rough estimate)

Density 

1.1985 (rough estimate)

refractive index 

1.5100 (estimate)

storage temp. 

Amber Vial, -20°C Freezer, Under inert atmosphere

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

4.97±0.70(Predicted)

color 

White to Pale Beige

Stability:

Light Sensitive

amisometradine Usage And Synthesis

Originator

Rolicton,Searle,US,1956

Uses

Amisometradine is an oral diuretic.

Definition

ChEBI: Amisometradine is a pyrimidone.

Manufacturing Process

Preparation of the ethyl analog is as follows (methyl isocyanate is used in amisometradine manufacture).
To a cooled and stirred solution of 142 parts of methallylamine in 900 parts of benzene, 156 parts of ethyl isocyanate are added dropwise. Upon concentration in vacuum N-ethyl-N'-methallylurea is obtained.
260 parts of this urea derivative are dissolved in 500 parts of acetic anhydride and treated with 157 parts of cyanoacetic acid at 60°C and heated at that temperature for 2 hours. The solution is then concentrated in vacuum to a syrup. 100 parts of water are added and the vacuum distillation is repeated. The remaining syrup contains a mixture of N-cyanoacetyl-N-ethyl-N'- methallylurea and a small quantity of N-cyanoacetyl-N-methallyl-N'-ethylurea.
This syrup is treated with sufficient 20% sodium hydroxide solution to raise the pH to 10. A violent reaction occurs. The reaction mixture is diluted with 50 parts of water, stirred, cooled and filtered. The material collected on the filter is recrystallized from 10% ethanol to yield a mixture of 1-methallyl-3-ethyl-6- amino-1,2,3,4-tetrahydro-2,4-pyrimidinedione and 1-ethyl-3-methallyl-6- amino-1,2,3,4-tetrahydro-2,4-pyrimidinedione melting at about 157-159°C.

Therapeutic Function

Diuretic

amisometradine(550-28-7)Related Product Information

• 6-amino-1-propyluracil
• 1,3-DIALLYLUREA
• amisometradine
• 1-ALLYLPYRIMIDINE-2,4(1H,3H)-DIONE
• 6-AMINO-1-ETHYL-1H-PYRIMIDINE-2,4-DIONE