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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Look at other dictionaries:

  • Agmatine — Structure de l agmatine Général Synonymes N 4 aminobutylguanidine …   Wikipédia en Français

  • agmatine — (= 1 amino 4 guanidobutane) A metabolite of arginine via arginine decarboxylase, is metabolized to putrescine by agmatinase. Suppresses polyamine biosynthesis and polyamine uptake by cells by inducing antizyme. Binds to imidazoline receptors and… …   Dictionary of molecular biology

  • agmatine — noun The amine (4 aminobutyl)guanidine which is a decarboxylation product of arginine and an intermediate in polyamine biosynthesis …   Wiktionary

  • agmatine — ag·ma·tine ag mə .tēn n a base C5H14N4 formed from arginine in putrefaction …   Medical dictionary

  • agmatine — ag·ma·tine …   English syllables

  • agmatine — ˌtēn noun ( s) Etymology: International Scientific Vocabulary agmat (from Greek agmat , agma fragment) + ine : a base C5H14N4 formed from arginine in putrefaction; (δ amino butyl) guanidine …   Useful english dictionary

  • Agmatine N4-coumaroyltransferase — In enzymology, an agmatine N4 coumaroyltransferase (EC number|2.3.1.64) is an enzyme that catalyzes the chemical reaction:4 coumaroyl CoA + agmatine ightleftharpoons CoA + N (4 guanidinobutyl) 4 hydroxycinnamamideThus, the two substrates of this… …   Wikipedia

  • Agmatine deiminase — In enzymology, an agmatine deiminase (EC number|3.5.3.12) is an enzyme that catalyzes the chemical reaction:agmatine + H2O ightleftharpoons N carbamoylputrescine + NH3Thus, the two substrates of this enzyme are agmatine and H2O, whereas its two… …   Wikipedia

  • Agmatine kinase — In enzymology, an agmatine kinase (EC number|2.7.3.10) is an enzyme that catalyzes the chemical reaction:ATP + agmatine ightleftharpoons ADP + N4 phosphoagmatineThus, the two substrates of this enzyme are ATP and agmatine, whereas its two… …   Wikipedia

  • AGMAT — Agmatine ureohydrolase (agmatinase), also known as AGMAT, is a human gene.cite web | title = Entrez Gene: AGMAT agmatine ureohydrolase (agmatinase)| url = http://www.ncbi.nlm.nih.gov/sites/entrez?Db=gene Cmd=ShowDetailView TermToSearch=79814|… …   Wikipedia


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