Aminoguanidine

Chemical Properties

Aminoguanidine is prepared from hydrazine and aqueous cyanamide solution. Processes based on the reduction of nitroguanidine have no industrial significance.

Chemical Properties

Aminoguanidine [CAS: 79-17-4], CH6N4, Mr 74.09, is a base that forms salts with both inorganic and organic acids. It is soluble in water and ethanol. Free aminoguanidine is stable for only a short time; therefore, it is marketed in the form of its stable salts. Commercially, aminoguanidine is offered as the bicarbonate salt [2582-30-1], a white powder of usually 99 % assay. The water solubility at room temperature is low (< 5 g/L). It is offered by most world-scale hydrazine producers (→Hydrazine). Other salts can be prepared from the bicarbonate by reaction with acid.

Uses

Inhibitor (advanced glycosylation end-product formation).

Definition

ChEBI: Aminoguanidine is a one-carbon compound whose unique structure renders it capable of acting as a derivative of hydrazine, guanidine or formamide. It has a role as an EC 1.4.3.4 (monoamine oxidase) inhibitor and an EC 1.14.13.39 (nitric oxide synthase) inhibitor. It is a member of guanidines and a one-carbon compound.

Enzyme inhibitor

This substituted hydrazine (FWhydrochloride = 110.55 g/mol; CAS 79-17-4), also named pimagedine, is a strong inhibitor of diamine oxidases as well as nitric oxide synthase. Note that aminoguanidine also inhibits the formation of advanced glycosylation end-products, reportedly by reacting with and trapping Amadori rearrangement-derived fragmentation products in solution. In view of this property, aminoguanidine has often been used to treat complications associated with chronic diabetes. Target(s): amine oxidase (copper-containing), or diamine oxidase; methylamine dehydrogenase; tryptophan tryptophylquinone enzymes; nitric-oxide synthase; b-fructofuranosidase, or invertase; monoamine oxidase, or amine oxidase; histidine decarboxylase; aldose reductase; catalase; formation of advanced glycosylation end products; adenosylmethionine decarboxylase; arginine deaminase; arginine kinase; aspartate aminotransferase; histamine N-methyltransferase.