2149-70-4

Basic information

• Product Name: N'-Nitro-L-arginine
• Synonyms: L-NNA;L-NO2ARG;L-NOARG;L-NG-NITROARGININE;L-NITROARGININE;L-NA;ARGININE(NO2)-OH;ARG(NO2)
• CAS NO: 2149-70-4
• Molecular Formula: C₆H₁₃N₅O₄
• Molecular Weight: 219.2
• EINECS: 218-418-9
• Product Categories: Amino Acids Derivatives;Amino Acids;Arginine [Arg, R];Amino Acids and Derivatives;Nitric Oxide
• Mol File: 2149-70-4.mol
• Article Data: 5

Chemical Properties

• Melting Point: 257 °C (dec.)(lit.)
• Boiling Point: 360°C (rough estimate)
• Flash Point: 233.5 °C
• Appearance: white to off-white powder
• Density: 1.4177 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.8000 (estimate)
• Storage Temp.: Store at RT.
• PKA: 2.49±0.24(Predicted)
• BRN: 1728914
• CAS DataBase Reference: N'-Nitro-L-arginine(CAS DataBase Reference)
• NIST Chemistry Reference: N'-Nitro-L-arginine(2149-70-4)
• EPA Substance Registry System: N'-Nitro-L-arginine(2149-70-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 22-24/25-36-26
• WGK Germany: 3
• RTECS: RM2982100
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 2149-70-4(Hazardous Substances Data)

Usage

Description

N'-Nitro-L-arginine, also known as L-NNA or NG-nitro-L-arginine, is an organic compound and a potent competitive inhibitor of nitric oxide synthase (NOS). It is a derivative of the amino acid L-arginine, with a nitro group (-NO2) attached to the nitrogen atom at the ω (omega) position. N'-Nitro-L-arginine is a white to off-white powder and is widely used in scientific research to study the role of nitric oxide in various biological processes.

Uses

Used in Pharmaceutical Research:
N'-Nitro-L-arginine is used as a research chemical for the inhibition of nitric oxide synthase, which is essential in understanding the role of nitric oxide in various physiological and pathological conditions. By inhibiting NOS, researchers can investigate the effects of nitric oxide on blood vessels, immune response, and neurotransmission.
Used in Bacteriology:
N'-Nitro-L-arginine is used as a tool in the study of bacteria, particularly to determine effective treatments against certain bacterial infections. It can help researchers understand the role of nitric oxide in bacterial pathogenesis and develop targeted therapies.
Used in the Study of MRSA (Methicillin-Resistant Staphylococcus Aureus):
N'-Nitro-L-arginine is employed in the research of MRSA, a type of antibiotic-resistant bacteria. By inhibiting nitric oxide synthase, researchers can study the effects of nitric oxide on MRSA's virulence, resistance mechanisms, and potential treatment strategies.

Hazard

A reproductive hazard.

Biological Activity

NO synthase inhibitor.

Biochem/physiol Actions

Nω-Nitro-L-arginine/L-NNA helps to reduce the levels of cortical hyperemia and brain cGMP occurring due to hypercapnia.

Safety Profile

Experimental reproductiveeffects. When heated to decomposition it emits toxicvapors of NOx.

InChI:InChI=1/C6H13N5O4/c7-6(8)9-3-1-2-4(5(12)13)10-11(14)15/h4,10H,1-3H2,(H,12,13)(H4,7,8,9)

Upstream product

• 57538-27-9 O-methyl-N-nitroisourea 
• 6211-16-1 dihydrochloride of (S)-ornithine 
• 1119-34-2 L-arginine hydrochloride 
• 2188-18-3 Boc-Arg(NO₂)-OH 
• 74-79-3 L-arginine 
• 157-06-2 D-arginine 

Downstream Products

• 51298-62-5 nitro-L-arginine methyl ester hydrochloride 
• 37682-82-9 N^ω-nitro-L-arginine ethyl ester; hydrochloride 
• 2304-98-5 N₅-[imino(nitroamino)methyl]-N₂-[(phenylmethoxy)carbonyl]-L-ornithine 
• 2188-18-3 Boc-Arg(NO₂)-OH 
• 23234-71-1 Z(OMe)-Arg(NO₂)-OH 
• 127488-84-0 Boc-FAKLNCR-CO₂H 
• 127488-85-1 Boc-LYR-CO₂H 
• 2418-67-9 L-Arg-Gly 
• 17461-53-9 (S)-2-[(S)-2-benzyloxycarbonylamino-3-(1H-indol-3-yl)-propanoylamino]-5-nitroguanidinopentanoic acid 
• 1052265-57-2 (S)-2-(2-benzyloxycarbonylamino-4-methylsulfanylbutyrylamino)-5-nitroguanidinopentanoic acid 
• 1052265-86-7 (5S,8S,11S)-5-benzyl-8-(2-(methylthio)ethyl)-11-(3-(nitroguanidino)propyl)-3,6,9-trioxo-1-phenyl-2-oxa-4,7,10-triazadodecan-12-oic acid 
• 1052265-84-5 (S)-2-[(S)-2-((S)-2-benzyloxycarbonylaminopropanoylamino)-3-(1H-indol-3-yl)propanoyl-amino]-5-nitroguanidinopentanoic acid 
• 1052265-88-9 (5S,8S,11S)-8-benzyl-5-(2-(benzyloxy)-2-oxoethyl)-11-(3-(nitroguanidino)propyl)-3,6,9-trioxo-1-phenyl-2-oxa-4,7,10-triazadodecan-12-oic acid 
• 1052265-90-3 (5S,11S)-8-benzyl-5-(2-(benzyloxy)-2-oxoethyl)-11-(3-(nitroguanidino)propyl)-3,6,9-trioxo-1-phenyl-2-oxa-4,7,10-triazadodecan-12-oic acid 

Relevant articles and documents

Direct monitoring of biocatalytic deacetylation of amino acid substrates by1H NMR reveals fine details of substrate specificity

Amino acids are key synthetic building blocks that can be prepared in an enantiopure form by biocatalytic methods. We show that thel-selective ornithine deacetylase ArgE catalyses hydrolysis of a wide-range ofN-acyl-amino acid substrates. This activity was revealed by1H NMR spectroscopy that monitored the appearance of the well resolved signal of the acetate product. Furthermore, the assay was used to probe the subtle structural selectivity of the biocatalyst using a substrate that could adopt different rotameric conformations.

Design, synthesis and primary activity assay of bi- or tri-peptide analogues with the scaffold l-arginine as amino-peptidase N/CD13 inhibitors

A series of bi- or tri-peptide analogues with the scaffold l-arginine were designed, synthesized and evaluated for their inhibitory activities against amino-peptidase N (APN) and metalloproteinase-2 (MMP-2). The primary activity assay showed that all the compounds exhibited higher inhibitory activities against APN than MMP-2. Within this series, compounds C6 and C7 (IC50 = 4.2 and 4.3 μM) showed comparable APN inhibitory activities with the positive control bestatin (IC50 = 3.8 μM).

A new method of reducing nitroarginine-peptide into arginine-peptide, with reference to the synthesis of poly-L-arginine hydrochloride.

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