51298-62-5

Basic information

• Product Name: N'-Nitro-L-arginine-methyl ester hydrochloride
• Synonyms: NG-nitro-L-Arg-OMe*HCl;L-Arg(NO2)-Ome·HCl;H-Aeg(NO2)-OMe.HCL;(S)-Methyl 2-amino-5-(3-nitroguanidino)-pentanoate hydrochloride;L-Ornithine, N5-[imino(nitroamino)methyl]-, methyl ester, hydrochloride (1:1);L-NG-Nitroarginine Methyl Ester (L-NAME);Nω-Nitro-L-arginine methyl ester hydrochloride (L-NAME);H-Arg(NO2)-OMe¤HC
• CAS NO: 51298-62-5
• Molecular Formula: C₇H₁₅N₅O₄
• Molecular Weight: 269.69
• EINECS: 257-116-1
• Product Categories: Inhibitors;Amino Acids Derivatives;Amino Acids;Arginine [Arg, R];Amino Acids and Derivatives;Amino Acid Methyl Esters;Amino Acids (C-Protected);Biochemistry;Amino hydrochloride;Nitric Oxide;Signalling
• Mol File: 51298-62-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: 157-161 °C (dec.)
• Boiling Point: 383.5 °C at 760 mmHg
• Flash Point: 185.8 °C
• Appearance: white to off-white/powder
• Vapor Pressure: 3.83E-07mmHg at 25°C
• Refractive Index: 15 ° (C=3, MeOH)
• Storage Temp.: 2-8°C
• Solubility: H2O: 50 mg/mL
• Water Solubility: almost transparency
• BRN: 3744166
• CAS DataBase Reference: N'-Nitro-L-arginine-methyl ester hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: N'-Nitro-L-arginine-methyl ester hydrochloride(51298-62-5)
• EPA Substance Registry System: N'-Nitro-L-arginine-methyl ester hydrochloride(51298-62-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 22-24/25-36-26
• WGK Germany: 3
• RTECS: RM2982570
• Hazardous Substances Data: 51298-62-5(Hazardous Substances Data)

Usage

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 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 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).

Biochem/physiol Actions

Primary TargeteNOS

InChI:InChI=1/C7H15N5O4.ClH/c1-16-6(13)5(8)3-2-4-10-7(9)11-12(14)15;/h5H,2-4,8H2,1H3,(H3,9,10,11);1H

Upstream product

• 67-56-1 methanol 
• 2149-70-4 N-nitro-L-arginine 
• 74-79-3 L-arginine 
• 112208-06-7 N^α-(tert-butoxycarbonyl)-N^G-nitro-L-arginine methyl ester 
• 2188-18-3 Boc-Arg(NO₂)-OH 
• 1119-34-2 L-arginine hydrochloride 

Downstream Products

• 2785-17-3 N^α-(N²-benzyloxycarbonyl-L-asparaginyl)-N^ω-nitro-L-arginine methyl ester 
• 98422-13-0 C₂₅H₃₂N₆O₇S 
• 96868-07-4 N^α-Benzyloxycarbonyl-N^ε-tosyl-L-lysyl-nitro-L-argininmethylester 
• 6464-79-5 Z-Phe-Arg(NO₂)-OCH₃ 
• 106386-19-0 N^α-(N²,N⁶-bis-benzyloxycarbonyl-L-lysyl)-N^ω-nitro-L-arginine methyl ester 
• 66345-00-4 C₁₈H₂₆N₆O₇ 
• 23734-44-3 Cbo-L-Val-nitro-L-Arg-methylester 
• 106655-93-0 -(nitro-L-arginin-methylester) 
• 106066-16-4 Cbo-L-Gly-(γ-benzylester)-nitro-L-Arg-methylester 
• 23734-44-3 Z-Val-Arg(NO₂)-OCH₃ 
• 23814-96-2 (Z)-Arg(NO₂)-Arg(NO₂)-OMe 
• 81666-53-7 Z-glycyl-N^G-nitro-L-arginine methyl ester 
• 26061-11-0 Boc-L-Phe-L-Arg^NO₂-OMe 
• 26061-11-0 Boc-Phe-Arg(NO₂)-OMe 

Relevant articles and documents

Novel L-arginine derivatives as aminopeptidase N inhibitors: design, chemistry, and pharmacological evaluation

Considering the important roles played in tumor, aminopeptidase N has been an appealing target for anti-tumor drug development. Here, a serial of novel aminopeptidase N inhibitors with L-arginine scaffold were designed, synthesized and evaluated for aminopeptidase N inhibitory activities. The preliminary anti-enzyme activity assay demonstrated that compounds 5e, 5h, 11e, 11g, and 11h showed comparable activities with the positive control bestatin, an approved aminopeptidase N inhibitor. In vitro anti-proliferation assay, compound 5f showed excellent activities against four kinds of tumor cells which overexpress aminopeptidase N. In vivo anti-metastasis assay, compounds 5f and 11g exhibited better activities than bestatin. So 5f and 11g should be lead compounds as novel aminopeptidase N inhibitors for further development.

A class of novel Schiff's bases: Synthesis, therapeutic action for chronic pain, anti-inflammation and 3D QSAR analysis

To discover analgesics for treating chronic pain 17 novel Schiff's bases, N,N′-(Z-allylidene-1,3-diyl)bisamino acid methyl esters were prepared from 1,1,3,3,-tetramethoxypropane and amino acid methyl esters. On tail-flick mouse model 20 μmol/kg of these Schiff's bases were orally administered, the analgesic action started 30 min after administration, reached the maximum 120 min after administration, and at 180 min this action was still observed. On a xylene-induced ear edema mouse model 20 μmol/kg of these Schiff's bases exhibited desirable anti-inflammation. Thus the present Schiff's bases are able to treat chronic pain from inflammation. The effect of the side chains of the amino acid residues of these Schiff's bases on the analgesic activity was explained with 3D QSAR.

AZIRIDINE ALDEHYDES, AZIRIDINE-CONJUGATED AMMO DERIVATIVES, AZIRIDINE-CONJUGATED BIOMOLECULES AND PROCESSES FOR THEIR PREPARATION

The present invention relates to unprotected amino aldehydes and applications for same. More particularly, the present invention relates to novel aziridine aldehydes and processes for preparing these novel compounds. The invention also relates to aziridine-conjugated amino derivatives, and processes for preparing the same. Pentacyclic compounds may be prepared using the aziridine aldehydes of the present invention, and the invention relates to these compounds and the processes by which they are made. The invention also relates to aziridine-conjugated bioactive molecules, such as amino acids and peptides, and processes for preparing such compounds.