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What is Agmatine ?

What is Agmatine ?

 Agmatine is a metabolite of the amino acid L-arginine which is generated via decarboxylation of L-arginine by the enzyme arginine decarboxylae (ADC) and further hydrolyzed to putrescine by the enzyme agmatinase. A third branch of arginine metabolism that produces agmatine has been reported to exist in the mammalian brain in 1994. Agmatine, also called 1-(4-Aminobutyl) guanidine, has the chemical formula H2N-CH2-CH2-CH2-CH2-NH-C(-NH2)(=NH), or C5H14N4 and a molecular weight of 130.19 g mol−1. Agmatine has been known as a natural compound for over 100 years but its biosynthesis in humans was not well understood until recently. The German scientist Albrecht Kossel first identified this substance from herring sperm and called it “agmatine”. Agmatine binds to several target receptors in the brain and is considered to be a novel neuromodulator. In animals, it potentiates morphine analgesia and reduces dependence and withdrawal. However, the exact mechanism is not clear. it has also been shown to have affinity to several transmembrane receptors, such as α2-adrenergic, imidazoline I1 and glutamatergic N-methyl-D-aspartate (NMDA) receptors. In additon, agmatine is known to be rapidly metabolized in the periphery and has poor penetration into the brain limiting its use as a therapeutic agent. Agmatine is packaged into the synaptic vesicles in the brain and spinal cord and acts on transmembrane receptors upon its depolarization-induced release. Inside the brain it is found at levels of >10 µM and is induced in response to stress and inflammation. Furthermore, it appears to be an endogenous neuromodulator of mental stress and may have beneficial effects in disorders such as depression, anxiety and post-traumatic stress disorders. Since agmatine has a primary amine group in its structure it can be analyzed using amino acid analysis, both using classical or more modern approaches.

Reference
Kossel, Albrecht 1910. Über das Agmatin. Zeitschrift für Physiologische Chemie 66: 257-261
Halaris A1, Plietz J.; Agmatine : metabolic pathway and spectrum of activity in brain. CNS Drug.<http://www.ncbi.nlm.nih.gov/pubmed/17927294> 2007;21(11):885-900.