Methylarginine (original) (raw)
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Methylarginine
 Stereo, skeletal formula of methylarginine (S)(S)-Methylarginine |
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| Names | |
| Other names2-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 NChEMBL109350 NChEMBL256147 N |
| ChemSpider | 4213 N2015298 (R) N117259 (S) N |
| KEGG | C03884 N |
| MeSH | omega-N-Methylarginine |
| PubChem CID | 43662733510 (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) NKey: NTNWOCRCBQPEKQ-UHFFFAOYSA-N N |
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| SMILES CNC(=N)NCCCC(N)C(O)=O | |
| Properties | |
| Chemical formula | C7H16N4O2 |
| Molar mass | 188.231 g·mol−1 |
| log P | −0.63 |
| Acidity (p_K_a) | 2.512 |
| Basicity (p_K_b) | 11.488 |
| Related compounds | |
| Related alkanoic acids | Asymmetric dimethylarginine_N_-Propyl-L-arginine |
| Related compounds | BuforminAcecarbromal |
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 |
Chemical compound
_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]
- ^ 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.
- ^ 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.
- ^ a b 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.