Agmatine
| Agmatine | |
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N-(4-Aminobutyl)guanidine[citation needed] |
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1-(4-Aminobutyl)guanidine[1] |
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Other names
(4-Aminobutyl)guanidine[citation needed] |
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| Identifiers | |
| CAS number | 306-60-5  |
| PubChem | 199 |
| ChemSpider | 194 |
| EC number | 206-187-7 |
| KEGG | C00179 |
| ChEBI | CHEBI:17431 |
| ChEMBL | CHEMBL58343 |
| 3DMet | B00052 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C5H14N4 |
| Molar mass | 130.19 g mol−1 |
| Exact mass | 130.121846468 g mol−1 |
| log P | −1.423 |
| Related compounds | |
| Related compounds | Biguanide |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
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.
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[edit] Clinical significance
Treatment with exogenous agmatine exerts neuroprotective effects in animal models of ischemia and neurotrauma.
[edit] History
The term "agmatine" was coined in 1910 by Albrecht Kossel, the German scientist who first identified the substance in herring sperm.[2]
[edit] See also
[edit] References
- ^ "agmatine (CHEBI:17431)". Chemical Entities of Biological Interest. UK: European Bioinformatics Institute. 15 August 2008. Main. https://www.ebi.ac.uk/chebi/searchId.do?chebiId=17431. Retrieved 11 January 2012.
- ^ Kossel, Albrecht 1910. Über das Agmatin. Zeitschrift für Physiologische Chemie 66: 257-261
[edit] Further reading
- Kim, J. H.; Yenari, M. A.; Giffard, R. G.; Cho, S. W.; Park, K. A.; Lee, J. E. (2004). "Agmatine reduces infarct area in a mouse model of transient focal cerebral ischemia and protects cultured neurons from ischemia-like injury". Experimental Neurology 189 (1): 122–130. doi:10.1016/j.expneurol.2004.05.029. PMID 15296842.
- Sa-Hyun Kim. Regulation of subventricular zone stem cell proliferation and differentiation by agmatine. Graduate School, Yonsei University. (2006) article[dead link]
- Wilcox, G.; Fiska, A.; Haugan, F.; Svendsen, F.; Rygh, L.; Tjolsen, A.; Hole, K. (2004). "Central sensitization". The Journal of Pain 5 (3): S19. doi:10.1016/j.jpain.2004.02.041.
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