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aminometradine

CAS No.
642-44-4
Chemical Name:
aminometradine
Synonyms
Mictine;Catapyrin;BRN 0175533;Aminometramide;aminometradine;1-allyl-6-amino-3-ethyl-pyrimidine-2,4-quinone;6-amino-3-ethyl-1-prop-2-enylpyrimidine-2,4-dione;6-azanyl-3-ethyl-1-prop-2-enyl-pyrimidine-2,4-dione;2,4(1H,3H)-Pyrimidinedione, 6-amino-3-ethyl-1-(2-propen-1-yl)-
CBNumber:
CB9920323
Molecular Formula:
C9H13N3O2
Molecular Weight:
195.221
MDL Number:
MFCD00086227
MOL File:
642-44-4.mol
Last updated:2023-05-04 17:34:41

aminometradine 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)
FDA UNII PPM8SX5Q3V

SAFETY

Risk and Safety Statements

Toxicity LD50 oral in rat: 2300mg/kg

aminometradine price

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich PH006926 1-allyl-6-amino-3-ethyl-2,4(1H,3H)-pyrimidinedione AldrichCPR 642-44-4 25MG $134 2023-06-20 Buy
TRC M344720 Mictine 642-44-4 25mg $160 2021-12-16 Buy
Medical Isotopes, Inc. 47738 Mictine 642-44-4 25mg $650 2021-12-16 Buy
Medical Isotopes, Inc. 47738 Mictine 642-44-4 250mg $2200 2021-12-16 Buy
Product number Packaging Price Buy
PH006926 25MG $134 Buy
M344720 25mg $160 Buy
47738 25mg $650 Buy
47738 250mg $2200 Buy

aminometradine Chemical Properties,Uses,Production

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

872828-38-1
642-44-4
Synthesis of aminometradine from Acetamide, 2-cyano-N-[(2-propen-1-ylamino)carbonyl]-

aminometradine Preparation Products And Raw materials

Raw materials

Preparation Products

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aminometradine 1-allyl-6-amino-3-ethyl-pyrimidine-2,4-quinone 6-amino-3-ethyl-1-prop-2-enylpyrimidine-2,4-dione 6-azanyl-3-ethyl-1-prop-2-enyl-pyrimidine-2,4-dione Mictine 2,4(1H,3H)-Pyrimidinedione, 6-amino-3-ethyl-1-(2-propen-1-yl)- Aminometramide BRN 0175533 Catapyrin 642-44-4