ChemicalBook Product Catalog Biochemical Engineering Amino Acids and Derivatives Arginine derivatives N'-Nitro-L-arginine-methyl ester hydrochloride

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

N'-Nitro-L-arginine-methyl ester hydrochloride Basic information
Product Name:N'-Nitro-L-arginine-methyl ester hydrochloride
Synonyms:L-NG-Nitroarginine Methyl Ester (L-NAME);Nω-Nitro-L-arginine methyl ester hydrochloride (L-NAME);L-Arg(NO2)-Ome·HCl;H-Aeg(NO2)-OMe.HCL;(S)-Methyl 2-amino-5-(3-nitroguanidino)-pentanoate hydrochloride;NG-nitro-L-Arg-OMe*HCl;L-Ornithine, N5-[imino(nitroamino)methyl]-, methyl ester, hydrochloride (1:1);2-(4-amino-5-oxohexyl)-1-nitroguanidine hydrochloride
CAS:51298-62-5
MF:C7H16ClN5O4
MW:269.69
EINECS:257-116-1
Product Categories:Inhibitors;Arginine [Arg, R];Amino Acids and Derivatives;Amino hydrochloride;Nitric Oxide;Signalling;Amino Acids Derivatives;Amino Acids;Amino Acid Methyl Esters;Amino Acids (C-Protected);Biochemistry
Mol File:51298-62-5.mol
N'-Nitro-L-arginine-methyl ester hydrochloride Structure
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
Water Solubility almost transparency
BRN 3744166
InChIKeyQBNXAGZYLSRPJK-JEDNCBNOSA-N
CAS DataBase Reference51298-62-5(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 Information
ProviderLanguage
SigmaAldrich English
ACROS English
N'-Nitro-L-arginine-methyl ester hydrochloride Usage And Synthesis
DescriptionL-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 Ki values of 15 nM, 39 nM, and 4.4 μM for nNOS (bovine), eNOS (human), and iNOS (mouse), respectively. The reported Ki 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 PropertiesCrystalline
UsesNitroarginine 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.
DefinitionChEBI: A hydrochloride obtained by combining Ngamma-nitro-L-arginine methyl ester with one equivalent of hydrochloric acid.
General DescriptionMore 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 ActivityNO synthase inhibitor.
Biochem/physiol ActionsPrimary TargeteNOS
storageRoom temperature
N'-Nitro-L-arginine-methyl ester hydrochloride Preparation Products And Raw materials
Methylparaben Methyl ACD/Index Name Pro Bensulfuron methyl 2-Propenenitrile, polymer with 1,3-butadiene, ethenylbenzene and 2-ethenylpyridine (9CI) (CA INDEX NAME) Parathion-methyl Topotecan hydrochloride ARGINASE N'-Nitro-L-arginine-methyl ester hydrochloride Kresoxim-methyl Arginine D-NAME L-Alanine methyl ester hydrochloride arginine aspirin Methyl acrylate Methyl bromide L(+)-Arginine L-Arginine hydrochloride
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