Agmatine

Title: Agmatine
CAS Registry Number: 306-60-5
CAS Name: 4-(Aminobutyl)guanidine
Additional Names: 1-amino-4-guanidobutane
Molecular Formula: C5H14N4
Molecular Weight: 130.19
Percent Composition: C 46.13%, H 10.84%, N 43.03%
Literature References: Decarboxylated arginine. Found in pollen of Ambrosia artemisifolia L., Compositae, in ergot, in sponges, in herring sperm, in octopus muscle: F. W. Heyl, J. Am. Chem. Soc. 41, 670 (1919); A. Kossel, Z. Physiol. Chem. 66, 257 (1910); J. L. Irvin, D. W. Wilson, J. Biol. Chem. 127, 565 (1939). Prepn of salts: DE 463576 (1928 to Schering-Kahlbaum AG). Synthesis: A. Kossel, Z. Physiol. Chem. 68, 170 (1910); K. Odo, J. Chem. Soc. Jpn. 67, 132 (1946); K. Dose, Ber. 90, 1251 (1957). Use as marker for tumor cells: F. S. Steven et al., Anticancer Res. 9, 247 (1989); F. S. Steven et al., J. Enzyme Inhib. 4, 63 (1990).
Derivative Type: Sulfate
CAS Registry Number: 2482-00-0
Molecular Formula: C5H14N4.H2SO4
Molecular Weight: 228.27
Percent Composition: C 26.31%, H 7.06%, N 24.54%, S 14.05%, O 28.04%
Properties: Needles from dil methanol, mp 231°. Fairly sol in water. Nearly insol in alcohol.
Melting point: mp 231°
Derivative Type: Gold chloride
Molecular Formula: C5H14N4.2HCl.2AuCl3
Molecular Weight: 809.76
Percent Composition: C 7.42%, H 1.99%, N 6.92%, Cl 35.03%, Au 48.65%
Properties: Yellow needles from water, dec 223°.
Use: Biochemical probe
Agomelatine Agroclavine Agrocybin Ahistan Ajaconine

Agmatine
Skeletal formula of an agmatine minor tautomer
Identifiers
CAS number 306-60-5 YesY
PubChem 199
ChemSpider 194 YesY
EC number 206-187-7
KEGG C00179 N
MeSH Agmatine
ChEBI CHEBI:17431 YesY
ChEMBL CHEMBL58343 YesY
3DMet B00052
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C5H14N4
Molar mass 130.19 g mol−1
Density 1.2 g/ml
Melting point 102 °C; 216 °F; 375 K
Boiling point 281 °C; 538 °F; 554 K
Solubility in water high
log P −1.423
Basicity (pKb) 0.52
Hazards
Flash point 95.8 °C; 204.4 °F; 368.9 K
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 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 or inactivates nitric oxide synthase (NOS), and it induces the release of some peptide hormones.