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]]