188. Agmatine

Nomenclature

CAS number: 306-60-5
4-(Aminobutyl)guanidine; 1-amino-4-guanidobutane.
C5H14N4; mol wt 130.19.
C 46.13%, H 10.84%, N 43.03%.

Description and 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).

Chemical structure

Derivative

Sulfate.

Nomenclature

CAS number: 2482-00-0
C5H14N4.H2SO4; mol wt 228.27.
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.

Derivative

Gold chloride.
C5H14N4.2HCl.2AuCl3; mol wt 809.76.
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