Trimethylamine N-oxide Trimethylamine N-oxide Trimethylamine "N"-oxide (TMAO) is an organic compound with the formula (CH)NO. It is in the class of amine oxides. Although the anhydrous compound is known, trimethylamine "N"-oxide is usually encountered as the dihydrate. It is a product of the oxidation of trimethylamine, a common metabolite in animals. Both the anhydrous and hydrated materials are white, water-soluble solids. Trimethylamine "N"-oxide is an osmolyte found in saltwater fishes, sharks, rays, molluscs, and crustaceans. It is considered as a protein stabilizer that may serve to counteract urea, the major osmolyte of sharks, skates and rays. It is also higher in deep-sea
Dihydrogen bond a normal N−H vibration whereas the lower energy band is assigned to the same bond, which is interacting with the B−H. Upon dilution of the solution, the 3300 cm band increased in intensity and the 3210 cm band decreased, indicative of intermolecular association. Interest in dihydrogen bonding was reignited upon the crystallographic characterization of the molecule HNBH. In this molecule, like the one studied by Brown and Hazeltine, the hydrogen atoms on nitrogen have a partial positive charge, denoted H, and the hydrogen atoms on boron have a partial negative charge, often denoted H. In other words, the amine is