Agmatine

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Template:Chembox E number
Agmatine
IUPAC name 2-(4-Aminobutyl)guanidine
Other names (4-Aminobutyl)guanidine
Identifiers
3D model (JSmol)
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Properties
C5H14N4
Molar mass 130.192 g/mol
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Agmatine ((4-aminobutyl)guanidine, NH2-CH2-CH2-CH2-CH2-NH-C(-NH2)(=NH)) is the decarboxylation product of the amino acid arginine and is an intermediate in polyamine biosynthesis. It is discussed as a putative neurotransmitter. It is synthesized in the brain, stored in synaptic vesicles, accumulated by uptake, released by membrane depolarization, and inactivated by agmatinase. Agmatine binds to α2-adrenergic receptor and imidazoline binding sites, and blocks NMDA receptors and other cation ligand-gated channels. Agmatine inhibits nitric oxide synthase (NOS), and induces the release of some peptide hormones. Treatment with exogenous agmatine exerts neuroprotective effects in animal models of neurotrauma.

The term "agmatine" was coined in 1910 by Albrecht Kossel, the German scientist who first identified the substance in herring sperm.[1]

References

  1. Kossel, Albrecht 1910. Über das Agmatin. Zeitschrift für Physiologische Chemie 66: 257-261
  • Jae-Hwan Kim, et al. Agmatine reduces infarct area in a mouse model of transient focal cerebral ischemia and protects cultured neurons from ischemia-like injury. Experimental Neurology. 189 (2004) 122– 130
  • Sa-Hyun Kim. Regulation of subventricular zone stem cell proliferation and differentiation by agmatine. Graduate School, Yonsei University. (2006) article



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