Chemistry:Methylarginine

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Methylarginine
Stereo, skeletal formula of methylarginine (S)
(S)-Methylarginine
Names
Other names
2-Amino-5-[(N’-methylcarbamimidoyl)amino]pentanoic acid; N-Monomethylarginine; omega-N-Methylarginine; Tilarginine; Targinine
Identifiers
3D model (JSmol)
2262067 (R)
ChEBI
ChEMBL
ChemSpider
KEGG
MeSH omega-N-Methylarginine
UNII
Properties
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
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 in the oldest subjects.[3]

An example of N-methylarginine soluble form, that has been used in a number of clinical research trials can be found here.[4]

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. "N-monomethyl arginine, an inhibitor of nitric oxide synthase, suppresses the development of adjuvant arthritis in rats". Arthritis & Rheumatology 37 (7): 1062–1069. 1994. doi:10.1002/art.1780370712. PMID 7517676. 
  3. 3.0 3.1 "Age-related reduction of NO availability and oxidative stress in human". Hypertension 38 (2): 274–279. 2012. 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.". 
  4. "L-NMMA Acetate 250 mg/Vial (Clinalfa basic)". https://www.bachem.com/fileadmin/user_upload/html/U-1090.html.