Aminoguanidine is the chemical compound with the formula . It is a versatile synthetic intermediate.
Aminoguanidine was studied as an investigational drug for the treatment of diabetic nephropathy, under the nonproprietary name Pimagedine, but never left the clinical trial phase due to side effects.
Chemistry Synthesis The industrial synthesis uses the reaction between cyanamide and hydrazine in aqueous solution.
The compound can also be obtained from the reduction of nitroguanidine with zinc in acetic acid.
Properties Aminoguanidine is a colorless solid that is soluble in water and ethanol. It is basic, producing salts when reacted with organic acids. As established by many crystallographic studies, protonation of aminoguanidine occurs at the imino nitrogen.
With formic acid, condensation occurs, leading to cyclization to give 3-amino-1,2,4-triazole.
The compound reacts with nitrous acid in acidic medium to give 5-aminotetrazole via the intermediate guanylazide.
At neutral pH, the reaction leads to tetrazene. Diazotization in acetic acid yields 1,3-di-(tetrazolyl)-triazene.
Investigational drug Pimagedine was investigated as a drug for kidney disease by the pharmaceutical company Alteon, but safety issues that appeared during clinical trials ended development before it was marketed and financial support was dropped for further trials.
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