Methylarginine

Methylarginine

(S)-Methylarginine
Names
Other names 2-Amino-5-[(N’-methylcarbamimidoyl)amino]pentanoic acid; N-Monomethylarginine; omega-N-Methylarginine
Identifiers
CAS Number	17035-90-4 (S) Y
3D model (Jmol)	Interactive image Interactive image
Beilstein Reference	2262067 (R)
ChEBI	CHEBI:28229 N
ChEMBL	ChEMBL312870 N ChEMBL109350 N ChEMBL256147 N
ChemSpider	4213 N 2015298 (R) N 117259 (S) N
KEGG	C03884 N
MeSH	omega-N-Methylarginine
PubChem	4366 2733510 (R) 132862 (S)
InChI InChI=1S/C7H16N4O2/c1-10-7(9)11-4-2-3-5(8)6(12)13/h5H,2-4,8H2,1H3,(H,12,13)(H3,9,10,11) N Key: NTNWOCRCBQPEKQ-UHFFFAOYSA-N N
SMILES C[nH]:c(:[nH]):[nH]CCCC(N)c(:[o]):[oH] CNC(=N)NCCCC(N)C(O)=O
Properties
Chemical formula	C7H16N4O2
Molar mass	188.23 g·mol−1
log P	−0.63
Acidity (pKa)	2.512
Basicity (pKb)	11.488
Related compounds
Related alkanoic acids	Asymmetric dimethylarginine N-Propyl-L-arginine
Related compounds	Buformin Acecarbromal
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

N-Methylarginine is an inhibitor of nitric oxide synthase. Chemically, it is a methyl derivative of the amino acid arginine. It is used as a biochemical tool in the study of physiological role of nitric oxide.

The inhibiting effect of N-methylarginine on vasodilation is lower in hypertensive patients than in normal subjects, indicating endothelial dysfunction. The inhibiting effect of N-methylarginine on vasodilation declines progressively with age, but has been restored with vitamin C (except in the oldest subjects).