Methylarginine

Methylarginine
	; (S)-Methylarginine
Names
	Other names 2-Amino-5-[(N’-methylcarbamimidoyl)amino]pentanoic acid; N-Monomethylarginine; omega-N-Methylarginine; Tilarginine; Targinine
Identifiers
CAS Number	17035-90-4 (S) ;
3D model (JSmol)	Interactive image;
Beilstein Reference	2262067 (R)
ChEBI	CHEBI:28229 ;
ChEMBL	ChEMBL312870 ; ChEMBL109350 ; ChEMBL256147 ;
ChemSpider	4213 ; 2015298 (R) ; 117259 (S) ;
KEGG	C03884 ;
MeSH	omega-N-Methylarginine
PubChem CID	4366; 2733510 (R); 132862 (S);
UNII	27JT06E6GR ;
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) Key: NTNWOCRCBQPEKQ-UHFFFAOYSA-N ;
	SMILES CNC(=N)NCCCC(N)C(O)=O;
Properties
Chemical formula	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	Asymmetric dimethylarginine; N-Propyl-L-arginine;
Related compounds	Buformin; Acecarbromal;
	Except where otherwise noted, data are 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 in the oldest subjects.^[3]

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. 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.

[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.

[pmid7517676-2] 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.

[pmid11509489-3] 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.

[1]

[2]

[3]

See also

References