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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 355085919 |
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| Watchedfields = changed |
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|ImageFile=L-Monomethylarginine.svg |
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| verifiedrevid = 442870188 |
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|ImageSize=200px |
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| ImageFile = L-Monomethylarginine.svg |
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|IUPACName=(2''S'')-2-Amino-5-pentanoic acid |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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|OtherNames=Targinina; Targininum; Targinine; omega-''N''-Methylarginine; <small>L</small>-Monomethylarginine; ''N''-Methyl-<small>L</small>-arginine; ''N''-Monomethyl-<small>L</small>-arginine; NG-monomethyl-<small>L</small>-arginine |
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| ImageCaption = (''S'')-Methylarginine |
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| ImageName = Stereo, skeletal formula of methylarginine (S) |
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| OtherNames = 2-Amino-5-pentanoic acid; ''N''-Monomethylarginine; ''omega''-''N''-Methylarginine; Tilarginine; Targinine |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo = 17035-90-4 |
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| Abbreviations = L-NMMA |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo=17035-90-4 |
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| CASNo_Comment = <small>(''S'')</small> |
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| PubChem=132862 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| SMILES=CN=C(N)NCCC(C(=O)O)N |
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| UNII = 27JT06E6GR |
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}} |
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| PubChem = 4366 |
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| PubChem1 = 2733510 |
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| PubChem1_Comment = <small>(''R'')</small> |
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| PubChem2 = 132862 |
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| PubChem2_Comment = <small>(''S'')</small> |
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| ChemSpiderID = 4213 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID1 = 2015298 |
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| ChemSpiderID1_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID1_Comment = <small>(''R'')</small> |
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| ChemSpiderID2 = 117259 |
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| ChemSpiderID2_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID2_Comment = <small>(''S'')</small> |
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| KEGG = C03884 |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| MeSHName = omega-N-Methylarginine |
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| ChEBI = 28229 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 312870 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL1 = 109350 |
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| ChEMBL1_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL2 = 256147 |
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| ChEMBL2_Ref = {{ebicite|changed|EBI}} |
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| Beilstein = 2262067 <small>(''R'')</small> |
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| SMILES = CNC(=N)NCCCC(N)C(O)=O |
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| 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) |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = NTNWOCRCBQPEKQ-UHFFFAOYSA-N |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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}} |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=7 | H=16 | N=4 | O=2 |
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| Formula=C<sub>7</sub>H<sub>16</sub>N<sub>4</sub>O<sub>2</sub> |
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| LogP = −0.63 |
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| MolarMass=188.23 g/mol |
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| pKa = 2.512 |
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| Appearance= |
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| pKb = 11.488 |
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| Density= |
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|Section3={{Chembox Hazards |
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| MainHazards= |
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| FlashPt= |
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| Autoignition= |
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}} |
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|Section3={{Chembox Related |
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| OtherFunction_label = alkanoic acids |
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| OtherFunction = {{unbulleted list|]|]}} |
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| OtherCompounds = {{unbulleted list|]|]}} |
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'''''N''-Methylarginine''' is an ] of ].<ref>{{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 }}</ref><ref name="pmid7517676">{{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 = ] | volume=37 | issue=7 | year=1994 | pages=1062–1069 | pmid=7517676| doi=10.1002/art.1780370712 | doi-access= }}</ref> Chemically, it is a ] derivative of the ] ]. It is used as a biochemical tool in the study of physiological role of ]. |
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The inhibiting effect of ''N''-methylarginine on ] is lower in ] patients than in normal subjects, indicating ].<ref name="pmid11509489">{{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= ] | 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 }}</ref> The inhibiting effect of ''N''-methylarginine on vasodilation declines progressively with age, but has been restored with ] in the oldest subjects.<ref name="pmid11509489" /> |
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'''''N''-Methylarginine''' is an ] of ].<ref>{{cite journal | author = Toutouzas, K.; Riga, M.; Stefanadi, E.; 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}}</ref> Chemically, it is a ] derivative of the ] ]. It is used as a biochemical tool in the study of physiological role of ]. |
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== See also == |
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==See also== |
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