Azoxymethane

• Dimethyldiazen -1-oxide
• (Z) -methyl- O, N, N- azoxymethane

Colorless liquid

0.991 g · cm -3

97-99 ° C

Risk

Template: Infobox chemical / molecular formula search available

Azoxymethane ( AOM) is a carcinogenic liquid and a derivative of azomethane.

Properties

Azoxymethane has a flash point of 24 ° C.

Carcinogenic effect

Azoxymethane is highly carcinogenic. In rodents, the administration of azoxymethane specifically induces the formation of colorectal carcinomas. The lesions correspond to the colon carcinogenesis in humans. For this reason, azoxymethane is used in oncology for the induction of colorectal cancer in experimental animals. To this end, the connection is usually administered subcutaneously or intraperitoneally.

In the liver azoxymethane is formed as a metabolite by the oxidation of 1,2- dimethylhydrazine (DMH ). DMH is thus the Prokarzinogen of azoxymethane. Azoxymethane is converted in the liver continues to methylazoxymethanol (MAM ). MAM is glucuronisiert and passes via the bile into the intestine end. The enzyme β -glucuronidase present there hydrolyzing the conjugate back to MAM. The β -glucuronidase can originate both from the bacteria of the intestinal flora, as well as from the intestinal epithelial cells. Methylazoxymethanol decomposes at 37 ° C with a half-life of 12 hours in N-methyl nitrosamine and a methyl radical. The methyl radical, the DNA in the nucleus to alkylate 6-O- methylguanine. The damage of the DNA is not fixed, the methylation results in the replication of a transition of guanine to adenine, which is caused by erroneous attachment of the 6-O -methylguanine with thymine.

Synthesis

Azoxymethane example, can be electrochemically produced from nitromethane.