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Methylarginine

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Methylarginine
Stereo, skeletal formula of methylarginine (S)
Stereo, skeletal formula of methylarginine (S)
(S)-Methylarginine
Names
Other names 2-Amino-5-pentanoic acid; N-Monomethylarginine; omega-N-Methylarginine; Tilarginine; Targinine
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 2262067 (R)
ChEBI
ChEMBL
ChemSpider
KEGG
MeSH omega-N-Methylarginine
PubChem CID
UNII
CompTox Dashboard (EPA)
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)Key: NTNWOCRCBQPEKQ-UHFFFAOYSA-N
SMILES
  • CNC(=N)NCCCC(N)C(O)=O
Properties
Chemical formula C7H16N4O2
Molar mass 188.231 g·mol
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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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 in the oldest subjects.

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. S2CID 260167230.
  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. doi:10.1002/art.1780370712. PMID 7517676.
  3. ^ 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. CiteSeerX 10.1.1.576.255. doi:10.1161/01.hyp.38.2.274. PMID 11509489. Up to the age of 60 years, despite the evident decline in endothelium-dependent vasodilation, vitamin C did not modify the response to acetylcholine. In contrast, in the oldest individuals (age >60 years) characterized by a profound alteration in NO availability, vitamin C not only enhanced the response to the endothelial agonist but also restored the inhibiting effect of L-NMMA on vasodilation to acetylcholine.
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