Agmatine

Agmatine
Systematic name 1-(4-Aminobutyl)guanidine[1]
Other names N-(4-Aminobutyl)guanidine[citation needed]
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
Exact mass	130.121846468 g mol−1
log P	−1.423
Related compounds
Related compounds	Diethylamine Triethylamine Diethylhydroxylamine Diisopropylamine Dimethylaminopropylamine Diethylenetriamine Diethylethanolamine Diethanolamine N,N-Diisopropylethylamine Triisopropylamine Tris(2-aminoethyl)amine N,N-Diisopropylaminoethanol Methyl diethanolamine Triethanolamine Mechlorethamine HN1 (nitrogen mustard) HN3 (nitrogen mustard) Dipropylamine Methyl-n-amylnitrosamine Norspermidine
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

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 ischemia and neurotrauma.^{[citation needed]}

History

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

See also

• Agmatine deiminase

References

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.  edit
• 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.  edit