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Agmatine
Agmatine.png
IUPAC name
Other names (4-Aminobutyl)guanidine
Identifiers
CAS number 306-60-5 Yes check.svgY
PubChem 199
SMILES
InChI
InChI key QYPPJABKJHAVHS-UHFFFAOYAX
ChemSpider ID 194
Properties
Molecular formula C5H14N4
Molar mass 130.19 g mol−1
 Yes check.svgY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Agmatine ((4-aminobutyl)guanidine, NH2-CH2-CH2-CH2-CH2-NH-C(-NH 2)(=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.

Contents

Clinical significance

Treatment with exogenous agmatine exerts neuroprotective effects in animal models of ischemia and neurotrauma.

History

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

See also

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
  • Central Sensitization: The endogenous NMDA antagonist and NOS inhibitor Agmatine inhibits spinal long term potentiation (G. Wilcox, A. Fiska, F. Haugan, F. Svendsen, L. Rygh, A. Tjolsen and K. Hole. American Pain Society. Published by Elsevier Science. 2004) [1]
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