NH2CHNH2COOH

NH2CHNH2COOH, also known as 2-amino-2-guanidinoacetic acid or glycocyamine, is a non-proteinogenic amino acid. It is an intermediate in the biosynthesis of creatine in vertebrates. Glycocyamine is synthesized in the kidney and liver from arginine and glycine. It is then transported to the liver and pancreas, where it is converted to creatine. Creatine is a molecule that stores high-energy phosphate groups in the form of phosphocreatine.

The primary function of glycocyamine is its role as a precursor to creatine. Creatine plays a vital role in energy metabolism, particularly in tissues with high and fluctuating energy demands, such as muscle and brain. It helps to rapidly replenish adenosine triphosphate (ATP), the main energy currency of cells, during short bursts of intense activity.

Glycocyamine itself has also been investigated for potential physiological effects. Some studies suggest it may have antioxidant properties and a role in regulating blood pressure. However, its significance in biological systems is predominantly linked to its metabolic conversion into creatine. Glycocyamine is not incorporated into proteins during translation and is not considered one of the standard 20 amino acids that make up proteins. Its presence and metabolism are specifically tied to the creatine synthesis pathway.