Agmatine

Agmatine

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ImageFile = Agmatine.png ImageSize = 200px
IUPACName = 2-(4-Aminobutyl)guanidine
OtherNames = (4-Aminobutyl)guanidine
Section1 = Chembox Identifiers
CASNo = 306-60-5
PubChem = 199
ChemSpiderID = 194
SMILES = C(CCN=C(N)N)CN
Section2 = Chembox Properties
C=5|H=14|N=4
MolarMass = 130.192 g/mol
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Section3 = Chembox Hazards
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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.

Clinical significance

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

History

The term "agmatine" was coined in 1910 by Albrecht Kossel, the German scientist who first identified the substance in herring sperm. [Kossel, Albrecht 1910. [http://vlp.mpiwg-berlin.mpg.de/references?id=lit18967 Über das Agmatin] . "Zeitschrift für Physiologische Chemie" 66: 257-261]

ee also

* Agmatine deiminase

References

*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) [http://library.yonsei.ac.kr/dlsearch/Theme/Yonsei/main.asp article]


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