AMINOGUANIDINE

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.

Chemical properties

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

The Uses of AMINOGUANIDINE

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.