Agmatine
907139
222722633
2008-06-30T20:08:13Z
192.124.243.161
{{Chembox new
| ImageFile = Agmatine.png
| ImageSize = 200px
| IUPACName = 2-(4-Aminobutyl)guanidine
| OtherNames = (4-Aminobutyl)guanidine
| Section1 = {{Chembox Identifiers
| CASNo = 306-60-5
| PubChem = 199
| SMILES = C(CCN=C(N)N)CN
}}
| Section2 = {{Chembox Properties
| C=5|H=14|N=4
| MolarMass = 130.192 g/mol
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
}}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| Autoignition =
}}
}}
'''Agmatine''' ((4-aminobutyl)[[guanidine]], NH<sub>2</sub>-CH<sub>2</sub>-CH<sub>2</sub>-CH<sub>2</sub>-CH<sub>2</sub>-NH-C(-NH<sub>2</sub>)(=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 vesicle]]s, accumulated by uptake, released by membrane depolarization, and inactivated by agmatinase. Agmatine binds to α<sub>2</sub>-[[adrenergic receptor]] and [[imidazoline]] binding sites, and blocks [[NMDA receptor]]s and other [[cation]] [[Ionotropic receptor|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.<ref>Kossel, Albrecht 1910. Über das Agmatin. ''Zeitschrift für Physiologische Chemie'' 66: 257-261</ref>
==See also==
* [[Agmatine deiminase]]
==References==
<div class="references-small"><references /></div>
*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]
[[Category:Amines]]
[[Category:Guanidines]]
[[Category:Metabolism]]
{{biochem-stub}}
{{Amino acid metabolism intermediates}}
[[pl:Agmatyna]]
[[de:Agmatin]]