Methylarginine
 (S)-Methylarginine | |
| Names | |
|---|---|
| Other names
2-Amino-5-[(N’-methylcarbamimidoyl)amino]pentanoic acid; N-Monomethylarginine; omega-N-Methylarginine | |
| Identifiers | |
| 2262067 (R) | |
17035-90-4 (S)  | |
| ChEBI | CHEBI:28229  |
| ChEMBL | ChEMBL312870 ChEMBL109350 ChEMBL256147 |
| ChemSpider | 4213 2015298 (R) 117259 (S) |
| |
| Jmol-3D images | Image Image |
| KEGG | C03884 |
| MeSH | omega-N-Methylarginine |
| PubChem | 4366 2733510 (R) 132862 (S) |
| |
| Properties | |
| Molecular 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 |
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| Related compounds |
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| Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
| verify (what is: /?) | |
| 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
- ↑ 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.
- ↑ 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.
- ↑ 3.0 3.1 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.