N'-Nitro-L-arginine-methyl ester hydrochloride Chemical Properties

Melting point:

157-161 °C (dec.)

alpha 

14.5 º (c=3, CH3OH)

refractive index 

15 ° (C=3, MeOH)

RTECS 

RM2982570

storage temp. 

-20°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 Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

22-24/25-36-26

WGK Germany 

3

HS Code 

29299090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

N'-Nitro-L-arginine-methyl ester hydrochloride Usage And Synthesis

Description

L-NAME requires hydrolysis of the methyl ester by cellular esterases to become a fully functional inhibitor (L-NNA). L-NNA exhibits some selectivity for inhibition of neuronal and endothelial isoforms. It exhibits K_i values of 15 nM, 39 nM, and 4.4 μM for nNOS (bovine), eNOS (human), and iNOS (mouse), respectively. The reported K_i value for the inhibition of iNOS ranges from 4-65 μM. 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.

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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