Methylarginine

N-Methylarginine is an inhibitor of nitric oxide synthase.^[1][2] 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.

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Methylarginine

(S)-Methylarginine
Names
Other names 2-Amino-5-[(N’-methylcarbamimidoyl)amino]pentanoic acid; N-Monomethylarginine; omega-N-Methylarginine; Tilarginine; Targinine
Identifiers
CAS Number	17035-90-4 (S) Y
3D model (JSmol)	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 CID	4366 2733510 (R) 132862 (S)
UNII	27JT06E6GR Y
CompTox Dashboard (EPA)	DTXSID50860196
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 CNC(=N)NCCCC(N)C(O)=O
Properties
Chemical formula	C7H16N4O2
Molar mass	188.231 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 verify (what is YN ?) Infobox references

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The inhibiting effect of N-methylarginine on vasodilation is lower in hypertensive patients than in normal subjects, indicating endothelial dysfunction.^[3] The inhibiting effect of N-methylarginine on vasodilation declines progressively with age, but has been restored with vitamin C in the oldest subjects.^[3]