| Identification | Back Directory | [Name]
aminometradine | [CAS]
642-44-4 | [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)- | [EINECS(EC#)]
211-384-6 | [Molecular Formula]
C9H13N3O2 | [MDL Number]
MFCD00086227 | [MOL File]
642-44-4.mol | [Molecular Weight]
195.221 |
| Chemical Properties | Back Directory | [Melting point ]
75-115°; mp 143-144° | [Boiling point ]
331.89°C (rough estimate) | [density ]
1.1985 (rough estimate) | [refractive index ]
1.5100 (estimate) |
| Hazard Information | Back Directory | [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 |
|
| Company Name: |
Energy Chemical
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021-58432009 400-005-6266 |
| Website: |
http://www.energy-chemical.com |
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