| Identification | More | [Name]
N'-Nitro-L-arginine-methyl ester hydrochloride | [CAS]
51298-62-5 | [Synonyms]
ARGININE(NO2)-OME HCL
H-ARG(NO2)-OME HCL
H-ARG(NO2)-OME HYDROCHLORIDE
L-NAME
L-NAME HCL
L-NAME HYDROCHLORIDE
L-NG-NITROARGININE METHYL ESTER HCL
L-NG-NITROARGININE METHYL ESTER HYDROCHLORIDE
N5-[IMINO(NITROAMINO)METHYL]-L-ORNITHINE, METHYL ESTER, MONOHYDROCHLORIDE
NG-NITRO-L-ARGININE-METHYL ESTER HCL
NG-NITRO-L-ARGININE METHYL ESTER HYDROCHLORIDE
N(G)-NITRO-L-ARGININE METHYL ESTER HYDROCHLORIDE SALT
NG-NO2-L-ARG-OME, HCL
NG-NO2-L-ARG-OME, HYDROCHLORIDE
NITRO-L-ARGININE METHYL ESTER HYDROCHLORIDE
N-NITRO-L-ARGININE METHYL ESTER HYDROCHLORIDE
N-OMEGA-NITRO-L-ARGININE METHYL ESTER HYDROCHLORIDE
N-OMEGA-NO2-L-ARG-OME, HCL
N-OMEGA-NO2-L-ARG-OME, HYDROCHLORIDE
S(+)-N5-[IMINO(NITROAMINO)METHYL]-L-ORNITHINE METHYL ESTER HYDROCHLORIDE | [EINECS(EC#)]
257-116-1 | [Molecular Formula]
C7H16ClN5O4 | [MDL Number]
MFCD00039052 | [Molecular Weight]
269.69 | [MOL File]
51298-62-5.mol |
| Chemical Properties | Back Directory | [Appearance]
Crystalline | [Melting point ]
157-161 °C (dec.) | [alpha ]
14.5 º (c=3, CH3OH) | [refractive index ]
15 ° (C=3, MeOH) | [RTECS ]
RM2982570 | [storage temp. ]
2-8°C
| [solubility ]
H2O: 50 mg/mL
| [form ]
powder
| [color ]
white to off-white
| [biological source]
synthetic | [Water Solubility ]
almost transparency | [BRN ]
3744166 | [InChIKey]
QBNXAGZYLSRPJK-JEDNCBNOSA-N | [CAS DataBase Reference]
51298-62-5(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [HS Code ]
29299090 |
| Hazard Information | Back Directory | [Description]
L-NAME requires hydrolysis of the methyl ester by cellular esterases to become a fully functional inhibitor (L-NNA).1 L-NNA exhibits some selectivity for inhibition of neuronal and endothelial isoforms. It exhibits Ki values of 15 nM, 39 nM, and 4.4 μM for nNOS (bovine), eNOS (human), and iNOS (mouse), respectively.2,3,4 The reported Ki value for the inhibition of iNOS ranges from 4-65 μM.3,5 L-NAME inhibits cGMP formation in endothelial cells with an IC50 of 3.1 μM (in the presence of 30 μM arginine) and reverses the vasodilation effects of acetylcholine in rat aorta rings with an EC50 of 0.54 μM.6,7 | [Chemical Properties]
Crystalline | [Uses]
Nitroarginine Methyl Ester Hydrochloride is used in the synthesis of N/CD13 inhibitors playing an important role in tumor invasion, metastatsis and angiogenesis. Also used in the preparation of spirocyclic lactam as a type II’ β-turn inducer. | [Definition]
ChEBI: A hydrochloride obtained by combining Ngamma-nitro-L-arginine methyl ester with one equivalent of hydrochloric acid. | [General Description]
More soluble analog of arginine and a competitive, slowly reversible inhibitor of endothelial nitric oxide synthase (IC50 = 500 nM). Causes a prolonged inhibition of acetylcholine-induced relaxation of rat aortic rings (IC50 = 400 nM). | [Biological Activity]
NO synthase inhibitor. | [Biochem/physiol Actions]
Primary TargeteNOS | [storage]
Room temperature | [References]
[1] C. K. BUCKNER. Analysis of Leukotriene Receptor Antagonists on Isolated Human Intralobar Airways[J]. Annals of the New York Academy of Sciences, 1988, 524 1: 181-186. DOI: 10.1111/j.1749-6632.1988.tb38540.x
[2] ERIC S. FURFINE. Selective inhibition of constitutive nitric oxide synthase by L-NG-nitroarginine[J]. Biochemistry Biochemistry, 1993, 32 33: 8512-8517. DOI: 10.1021/bi00084a017
[3] H M ABU-SOUD. Electron transfer in the nitric-oxide synthases. Characterization of L-arginine analogs that block heme iron reduction.[J]. The Journal of Biological Chemistry, 1994, 269 51: 32318-32326.
[4] D.D. REES. Characterization of three inhibitors of endothelial nitric oxide synthase in vitro and in vivo[J]. British Journal of Pharmacology, 1990, 101 3: 746-752. DOI: 10.1111/j.1476-5381.1990.tb14151.x
[5] P.K. MOORE. l-NG-nitro arginine (l-NOARG), a novel, l-arginine-reversible inhibitor of endothelium-dependent vasodilatation in vitro[J]. British Journal of Pharmacology, 1990, 99 2: 408-412. DOI: 10.1111/j.1476-5381.1990.tb14717.x
[6] LINLIN LI. iNOS-derived nitric oxide promotes glycolysis by inducing pyruvate kinase M2 nuclear translocation in ovarian cancer.[J]. Oncotarget, 2017, 8 20: 33047-33063. DOI: 10.18632/oncotarget.16523
[7] SABRINA JARAZO DIETRICH. Inhibition of NOS-NO System Prevents Autoimmune Orchitis Development in Rats: Relevance of NO Released by Testicular Macrophages in Germ Cell Apoptosis and Testosterone Secretion.[J]. PLoS ONE, 2015: e0128709. DOI: 10.1371/journal.pone.0128709
[8] COURTNEY PREMER. Allogeneic Mesenchymal Stem Cells Restore Endothelial Function in Heart Failure by Stimulating Endothelial Progenitor Cells.[J]. EBioMedicine, 2015, 2 5: 467-475. DOI: 10.1016/j.ebiom.2015.03.020
[9] JEFF REESE . Regulation of the fetal mouse ductus arteriosus is dependent on interaction of nitric oxide and COX enzymes in the ductal wall[J]. Prostaglandins & other lipid mediators, 2009, 88 3: Pages 89-96. DOI: 10.1016/j.prostaglandins.2008.11.001 |
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