Methylarginine

Methylarginine

(S)-Methylarginine
Names
Other names
2-Amino-5-[(N’-methylcarbamimidoyl)amino]pentanoic acid; N-Monomethylarginine; omega-N-Methylarginine
Identifiers
17035-90-4 (S) YesY
2262067 (R)
ChEBI CHEBI:28229 N
ChEMBL ChEMBL312870 N
ChEMBL109350 N
ChEMBL256147 N
ChemSpider 4213 N
2015298 (R) N
117259 (S) N
Jmol interactive 3D Image
Image
KEGG C03884 N
MeSH omega-N-Methylarginine
PubChem 4366
2733510 (R)
132862 (S)
Properties
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
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

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.

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 (except in the oldest subjects).[3]

See also

References

  1. Toutouzas, K.; Riga, M.; Stefanadi, E.; Stefanadis, C. (2008). "Asymmetric dimethylarginine (ADMA) and other endogenous nitric oxide synthase (NOS) inhibitors as an important cause of vascular insulin resistance". Hormone and Metabolic Research 40 (9): 655–659. doi:10.1055/s-0028-1083814. PMID 18792879.
  2. Stefanovic-Racic M, Meyers K, Meschter C, Coffey JW, Hoffman RA, Evans CH (1994). "N-monomethyl arginine, an inhibitor of nitric oxide synthase, suppresses the development of adjuvant arthritis in rats". Arthritis & Rheumatology 37 (7): 1062–1069. PMID 7517676.
  3. 1 2 Taddei S, Virdis A, Ghiadoni L, Salvetti G, Bernini G, Magagna A, Salvetti A (2012). "Age-related reduction of NO availability and oxidative stress in human". Hypertension 38 (2): 274–279. PMID 11509489.
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