Methylarginine

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 442870188

| ImageFile = L-Monomethylarginine.svg

| ImageFile_Ref = {{chemboximage|correct|??}}

| ImageCaption = (S)-Methylarginine

| ImageName = Stereo, skeletal formula of methylarginine (S)

| OtherNames = 2-Amino-5-[(N’-methylcarbamimidoyl)amino]pentanoic acid; N-Monomethylarginine; omega-N-Methylarginine; Tilarginine; Targinine

|Section1={{Chembox Identifiers

| CASNo = 17035-90-4

| CASNo_Ref = {{cascite|correct|??}}

| CASNo_Comment = (S)

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 27JT06E6GR

| PubChem = 4366

| PubChem1 = 2733510

| PubChem1_Comment = (R)

| PubChem2 = 132862

| PubChem2_Comment = (S)

| ChemSpiderID = 4213

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID1 = 2015298

| ChemSpiderID1_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID1_Comment = (R)

| ChemSpiderID2 = 117259

| ChemSpiderID2_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID2_Comment = (S)

| KEGG = C03884

| KEGG_Ref = {{keggcite|changed|kegg}}

| MeSHName = omega-N-Methylarginine

| ChEBI = 28229

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 312870

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL1 = 109350

| ChEMBL1_Ref = {{ebicite|changed|EBI}}

| ChEMBL2 = 256147

| ChEMBL2_Ref = {{ebicite|changed|EBI}}

| Beilstein = 2262067 (R)

| SMILES = CNC(=N)NCCCC(N)C(O)=O

| StdInChI = 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)

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = NTNWOCRCBQPEKQ-UHFFFAOYSA-N

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

}}

|Section2={{Chembox Properties

| C=7 | H=16 | N=4 | O=2

| LogP = −0.63

| pKa = 2.512

| pKb = 11.488

}}

|Section3={{Chembox Related

| OtherFunction_label = alkanoic acids

| OtherFunction = {{unbulleted list|Asymmetric dimethylarginine|N-Propyl-L-arginine}}

| OtherCompounds = {{unbulleted list|Buformin|Acecarbromal}}

}}

}}

N-Methylarginine is an inhibitor of nitric oxide synthase.{{cite journal |author1=Toutouzas, K. |author2=Riga, M. |author3=Stefanadi, E. |author4=Stefanadis, C. | title = Asymmetric dimethylarginine (ADMA) and other endogenous nitric oxide synthase (NOS) inhibitors as an important cause of vascular insulin resistance | journal = Hormone and Metabolic Research | year = 2008 | volume = 40 | issue = 9 | pages = 655–659 | doi = 10.1055/s-0028-1083814 | pmid = 18792879|s2cid=260167230 }}{{cite journal |vauthors=Stefanovic-Racic M, Meyers K, Meschter C, Coffey JW, Hoffman RA, Evans CH | title=N-monomethyl arginine, an inhibitor of nitric oxide synthase, suppresses the development of adjuvant arthritis in rats | journal = Arthritis & Rheumatology | volume=37 | issue=7 | year=1994 | pages=1062–1069 | pmid=7517676| doi=10.1002/art.1780370712 | doi-access= }} 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.{{cite journal |vauthors=Taddei S, Virdis A, Ghiadoni L, Salvetti G, Bernini G, Magagna A, Salvetti A | title=Age-related reduction of NO availability and oxidative stress in human | journal= Hypertension | volume=38 | issue=2 | year=2012 | pages=274–279 | pmid=11509489 | quote=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.| doi=10.1161/01.hyp.38.2.274 | doi-access=free | citeseerx=10.1.1.576.255 }} The inhibiting effect of N-methylarginine on vasodilation declines progressively with age, but has been restored with vitamin C in the oldest subjects.