6022. NG-Methylarginine

Nomenclature

CAS number: 17035-90-4
N5-[Imino(methylamino)methyl]-l-ornithine; tilarginine; targinine; NG-monomethyl-l-arginine; l-NMA.
C7H16N4O2; mol wt 188.23.
C 44.67%, H 8.57%, N 29.77%, O 17.00%.

Description and references

Nitric oxide synthase (NOS) inhibitor; naturally occurring analog of arginine. Isoln from bovine brain and prepn: T. Nakajima et al., Biochim. Biophys. Acta 230, 212 (1971). Improved prepn: J. L. Corbin, M. Reporter, Anal. Biochem. 57, 310 (1974); S. Pundak, M. Wilchek, J. Org. Chem. 46, 808 (1981); of acetate salt: W. Zhang et al., Synth. Commun. 24, 2789 (1994). Inhibition of NO release by endothelial cells: R. M. J. Palmer et al., Biochem. Biophys. Res. Commun. 153, 1251 (1988). Review of biological significance: J. Leiper, P. Vallance, Cardiovasc. Res. 43, 542-548 (1999). Clinical evaluation in cardiogenic shock: G. Cotter et al., Circulation 101, 1358 (2000).

Chemical structure

Properties

Crystals from water-ethanol. [α]D25 +26° (c = 1 in 1N HCl).

Derivative

Acetate.

Nomenclature

CAS number: 53308-83-1
C7H16N4O2.C2H4O2; mol wt 248.28.
C 43.54%, H 8.12%, N 22.57%, O 25.78%.

Properties

White granular solid. [α]D22 +9.5° (c = 0.10 in water). Sol in water.

Use

Reagent to inhibit nitric oxide production in biological systems.

Therapeutic Category

In treatment of cardiogenic shock.