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{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 355085919
| Watchedfields = changed
⚫ |ImageFile=L-Monomethylarginine.svg
⚫ | verifiedrevid = 442870188
|ImageSize=200px
⚫ | ImageFile = L-Monomethylarginine.svg
|IUPACName=(2''S'')-2-Amino-5-pentanoic acid
| ImageFile_Ref = {{chemboximage|correct|??}}
|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
| ImageCaption = (''S'')-Methylarginine
| ImageName = Stereo, skeletal formula of methylarginine (S)
| OtherNames = 2-Amino-5-pentanoic acid; ''N''-Monomethylarginine; ''omega''-''N''-Methylarginine; Tilarginine; Targinine
|Section1={{Chembox Identifiers |Section1={{Chembox Identifiers
⚫ | CASNo = 17035-90-4
| Abbreviations = L-NMMA
| CASNo_Ref = {{cascite|correct|??}}
⚫ | CASNo=17035-90-4
| CASNo_Comment = <small>(''S'')</small>
⚫ | PubChem=132862
| UNII_Ref = {{fdacite|correct|FDA}}
| SMILES=CN=C(N)NCCC(C(=O)O)N
| UNII = 27JT06E6GR
⚫ }}
⚫ | PubChem = 4366
| PubChem1 = 2733510
| PubChem1_Comment = <small>(''R'')</small>
| PubChem2 = 132862
| PubChem2_Comment = <small>(''S'')</small>
| ChemSpiderID = 4213
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID1 = 2015298
| ChemSpiderID1_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID1_Comment = <small>(''R'')</small>
| ChemSpiderID2 = 117259
| ChemSpiderID2_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID2_Comment = <small>(''S'')</small>
| 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 <small>(''R'')</small>
| 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 |Section2={{Chembox Properties
| C=7 | H=16 | N=4 | O=2
| Formula=C<sub>7</sub>H<sub>16</sub>N<sub>4</sub>O<sub>2</sub>
| LogP = −0.63
| MolarMass=188.23 g/mol
| pKa = 2.512
| Appearance=
| pKb = 11.488
| Density=
| MeltingPt=
| BoilingPt=
| Solubility=
⚫ }}
⚫ |Section3={{Chembox Hazards
| MainHazards=
| FlashPt=
| Autoignition=
⚫ }}
}} }}
⚫ |Section3={{Chembox Related
| OtherFunction_label = alkanoic acids
| OtherFunction = {{unbulleted list|]|]}}
| OtherCompounds = {{unbulleted list|]|]}}
⚫ }}
⚫ }}

⚫ '''''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 ].


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" />
⚫ '''''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 ].


== See also == ==See also==
* ] * ]


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{{reflist}} {{reflist}}


] ]
] ]

Latest revision as of 17:17, 15 March 2024

Methylarginine
Stereo, skeletal formula of methylarginine (S)
(S)-Methylarginine
Names
Other names 2-Amino-5-pentanoic acid; N-Monomethylarginine; omega-N-Methylarginine; Tilarginine; Targinine
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 2262067 (R)
ChEBI
ChEMBL
ChemSpider
KEGG
MeSH omega-N-Methylarginine
PubChem CID
UNII
CompTox Dashboard (EPA)
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
log P −0.63
Acidity (pKa) 2.512
Basicity (pKb) 11.488
Related compounds
Related alkanoic acids
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

N-Methylarginine is an inhibitor of nitric oxide synthase. 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. The inhibiting effect of N-methylarginine on vasodilation declines progressively with age, but has been restored with vitamin C in the oldest subjects.

See also

References

  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.
  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.
  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.
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