Agmatine

Agmatine
	IUPAC name 1-(4-Aminobutyl)guanidine
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; Image 2
	SMILES NCCCC[nH]:c(:[nH]):[nH2] NCCCCNC(N)=N ;
	InChI InChI=1S/C5H14N4/c6-3-1-2-4-9-5(7)8/h1-4,6H2,(H4,7,8,9) ; Key: QYPPJABKJHAVHS-UHFFFAOYSA-N ;
Properties
Molecular formula	C5H14N4
Molar mass	130.19 g mol−1
Density	1.2 g/ml
Boiling point	281 °C, 554 K, 538 °F
log P	−1.423
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references

Agmatine ((4-aminobutyl)guanidine) 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 it induces the release of some peptide hormones.

History [edit]

The term "agmatine" was coined in 1910 by Albrecht Kossel, the German scientist who first identified the substance in herring sperm.^[2]

Treatment with exogenous agmatine exerts neuroprotective effects in animal models of ischemia and neurotrauma.^[3]

^ "agmatine (CHEBI:17431)". Chemical Entities of Biological Interest. UK: European Bioinformatics Institute. 15 August 2008. Main. Retrieved 11 January 2012.
^ Kossel, Albrecht 1910. Über das Agmatin. Zeitschrift für Physiologische Chemie 66: 257-261
^ 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. edit

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. edit

Agmatine

IUPAC name 1-(4-Aminobutyl)guanidine^[1]
Identifiers
CAS number	306-60-5^Y
PubChem	199
ChemSpider	194^Y
EC number	206-187-7
KEGG	C00179^Y
ChEBI	CHEBI:17431^Y
ChEMBL	CHEMBL58343^Y
3DMet	B00052
Jmol-3D images	Image 1 Image 2
SMILES NCCCC[nH]:c(:[nH]):[nH2] NCCCCNC(N)=N
InChI InChI=1S/C5H14N4/c6-3-1-2-4-9-5(7)8/h1-4,6H2,(H4,7,8,9)^Y Key: QYPPJABKJHAVHS-UHFFFAOYSA-N^Y
Properties
Molecular formula	C₅H₁₄N₄
Molar mass	130.19 g mol⁻¹
Density	1.2 g/ml
Boiling point	281 °C, 554 K, 538 °F
log P	−1.423
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references