What molecule am I?
Agmatine, aka 1-(4-aminobutyl)guanidine, is a natural substance that is formed by the decarboxylation of the amino acid l-arginine, the Molecule of the Week for September 25, 2017. Agmatine belongs to a group of molecules called biogenic amines (BAs), which includes former MOTWs histamine, tyramine, putrescine, cadaverine, spermidine, and spermine. Agmatine and other BAs are particularly abundant in high-protein foods such as meats and dairy products.
In 1910, biochemist Albrecht Kossel at the Heidelberg Academy of Sciences (Germany) discovered agmatine in herring roe and reported a synthesis of it. Kossel was awarded the Nobel Prize in Physiology or Medicine the same year for his discoveries in cell biology. Nine years later, in an extensive study, Frederick W. Heyl at Upjohn (Kalamazoo, MI) reported the presence of agmatine in pollen protein extracts from ragweed (Ambrosia artemisiifolia).
Agmatine has a variety of biochemical properties. It can modify neurotransmitter systems, ion channels, nitric oxide (NO) synthesis, and polyamine metabolism. In a 1994 article, G. Li and co-workers at Cornell University Medical College (New York City) reported that agmatine is formed in the bovine brain and displaces clonidine by binding to α-2-adrenergic and imidazoline receptors. They also state that agmatine may act as a neurotransmitter.
Agmatine is is described as an important biomolecule in the 2021 book Starving Cancer Cells: Evidence-Based Strategies to Slow Cancer Progression by Robert Fried, Richard M. Carlton, and Dennis A. Fried. They cite a study in which agmatine abolished ornithine decarboxylase protein expression and polyamines biosynthesis to induce caspase-dependent apoptosis, and another that showed that it inhibited NO production mainly by depressing inducible NO synthase activity.
Learn more about this molecule from CAS, the most authoritative and comprehensive source for chemical information.