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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.

2149-70-4

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2149-70-4 Usage

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.

Check Digit Verification of cas no

The CAS Registry Mumber 2149-70-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,1,4 and 9 respectively; the second part has 2 digits, 7 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 2149-70:
(6*2)+(5*1)+(4*4)+(3*9)+(2*7)+(1*0)=74
74 % 10 = 4
So 2149-70-4 is a valid CAS Registry Number.
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)

2149-70-4 Well-known Company Product Price

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  • TCI America

  • (N0660)  Nω-Nitro-L-arginine  >98.0%(HPLC)(T)

  • 2149-70-4

  • 5g

  • 390.00CNY

  • Detail
  • TCI America

  • (N0660)  Nω-Nitro-L-arginine  >98.0%(HPLC)(T)

  • 2149-70-4

  • 25g

  • 1,250.00CNY

  • Detail
  • Alfa Aesar

  • (H62061)  Nomega-Nitro-L-arginine, 98%   

  • 2149-70-4

  • 5g

  • 382.0CNY

  • Detail
  • Alfa Aesar

  • (H62061)  Nomega-Nitro-L-arginine, 98%   

  • 2149-70-4

  • 25g

  • 1529.0CNY

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  • Sigma

  • (N5501)  Nω-Nitro-L-arginine  ≥98% (TLC)

  • 2149-70-4

  • N5501-1G

  • 211.77CNY

  • Detail
  • Sigma

  • (N5501)  Nω-Nitro-L-arginine  ≥98% (TLC)

  • 2149-70-4

  • N5501-5G

  • 542.88CNY

  • Detail
  • Sigma

  • (N5501)  Nω-Nitro-L-arginine  ≥98% (TLC)

  • 2149-70-4

  • N5501-25G

  • 2,122.38CNY

  • Detail

2149-70-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name N'-Nitro-L-arginine

1.2 Other means of identification

Product number -
Other names Nomega-nitro-L-arginine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:2149-70-4 SDS

2149-70-4Relevant articles and documents

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

De Cesare, Silvia,McKenna, Catherine A.,Mulholland, Nicholas,Murray, Lorna,Bella, Juraj,Campopiano, Dominic J.

supporting information, p. 4904 - 4909 (2021/06/16)

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.

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

Mou, Jiajia,Luan, Yepeng,Chen, Danghui,Wang, Qiang

, p. 3015 - 3025 (2017/10/06)

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.

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

Mou, Jiajia,Fang, Hao,Liu, Yingzi,Shang, Luqing,Wang, Qiang,Zhang, Lei,Xu, Wenfang

scheme or table, p. 887 - 895 (2010/05/02)

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).

Design, synthesis and primary activity evaluation of l-arginine derivatives as amino-peptidase N/CD13 inhibitors

Mou, Jiajia,Fang, Hao,Jing, Fanbo,Wang, Qiang,Liu, Yingzi,Zhu, Huawei,Shang, Luqing,Wang, Xuejian,Xu, Wenfang

scheme or table, p. 4666 - 4673 (2009/12/01)

A series of l-arginine derivatives were designed, synthesized and assayed for their activities against amino-peptidase N (APN)/CD13 and metalloproteinase-2 (MMP-2). The results showed that most compounds exhibited high inhibitory activities against APN and low activities against MMP-2. Within this series, two compounds 5q and 5s (IC50 = 5.3 and 5.1 μM) showed similar inhibitory activities compared with bestatin (IC50 = 3.8 μM), which could be used as novel lead compounds for the future APN inhibitors development as anticancer agents.

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