Reactions<unk>  reacts with DNA to form adducts. It is more reactive toward DNA than acrylamide. Several<unk> -DNA adducts have been characterized. The main DNA adducts are N7-(2-carbamoyl-2-hydroxyethyl)-guanine (or N7-GA-Gua) and N3-(2-carbamoyl-2-hydroxyethyl)adenine (or N3-GA-Ade).<unk>  also reacts with haemoglobine (Hb) to form a cysteine adduct, S-(20hydroxy-2carboxyethyl)cysteine. With this reaction, N-terminal valine adducts are also formed. Mechanism of action According to a major review, acrylamide "is extensively metabolized, mostly by conjugation with glutathione but also by epoxidation to<unk>  (GA). Formation of GA is considered to represent the route underlying the genotoxicity and carcinogenicity of acrylamide. The reaction of<unk>  and glutathione represents a detoxification pathway."<unk>  inhibits the sodium/potassium ATPase protein present in the plasma membrane of nerve cells. Intracellular sodium increases and intracellular potassium decreases due to this inhibition. This causes depolarization of the nerve membrane. The depolarization triggers a reverse sodium/calcium exchange, which will cause calcium-mediated axon degeneration. Metabolism The liver is a very active organ in the metabolism of xenobiotics. Substances in the liver modify the compounds to make them more soluble in water, in order to excrete them through bile and urine. In the case of acrylamide, this metabolic strategy result in a greater toxicity of the compound. Whether this is the case for<unk>  remains unclear.<unk>  can be detoxified through diverse pathways such as the formation of<unk> -glutathione conjugates. Both an enzymatic pathway via glutathione-S-transferase and a non-enzymatic pathway exist. These<unk> -glutathione conjugates are further metabolized to mercapturic acids by various peptidases and transferases, such as gamma-glutamyl-transpeptidase, dipeptidase, and N-acetyltransferase. The mercapturic acids that can be formed are N-acetyl-S-(2-carbamoylethyl)-cysteine (AAMA), N-acetyl-S-(1-carbamoyl-2-hydroxyethyl)-cysteine (GAMA2), and N-acetyl-S-(2-carbamoyl-2-hydroxyethyl)-cysteine (GAMA3) (Huang et al., 2011). These mercapturic acids are excreted through urine.<unk>  can also be hydrolyzed to glyceramide both spontaneously or enzymatically by microsomal epoxide hydrolase. This too can be excreted through urine. Animal studies Mice and rats show mutations and DNA adducts consistent with those arising from<unk> . Another study found tumors in the mice bodies after treatment with<unk>  A study by National Toxicology Program (2014) provided evidence of carcinogenic activity of<unk>  in several species of rats and mice. For two years, rats and mice were exposed to varying doses of<unk>  in drinking water. In the rats and mice were several carcinogenic effects found, such as carcinomas, fibroadenomas and malignant mesotheliomas.
Glycidamide
Dimethyllysergamide
Glucuronide
Pyrovalerone
Tuaminoheptane
Geritol
Diallyllysergamide
Kaurenoic acid