N5501

Sigma-Aldrich

Nω-Nitro-L-arginine

≥98% (TLC)

Synonym(s):
N5-(Nitroamidino)-L-2,5-diaminopentanoic acid, NG-NO2-L-Arg, L-NNA
Empirical Formula (Hill Notation):
C6H13N5O4
CAS Number:
Molecular Weight:
219.20
Beilstein/REAXYS Number:
1728914
EC Number:
MDL number:
PubChem Substance ID:
Pricing and availability is not currently available.

biological source

synthetic

assay

≥98% (TLC)

form

powder

mp

257 °C

solubility

1 M HCl: 50 mg/mL, clear, colorless to faintly yellow

SMILES string

NC@@H(CCCNC(=N)NN+(O-)=O)C(O)=O

InChI

1S/C6H13N5O4/c7-4(5(12)13)2-1-3-9-6(8)10-11(14)15/h4H,1-3,7H2,(H,12,13)(H3,8,9,10)/t4-/m0/s1

InChI key

MRAUNPAHJZDYCK-BYPYZUCNSA-N

Gene Information

human ... NOS1(4842), NOS2(4843), NOS2B(201288), NOS2C(645740), NOS3(4846)
mouse ... Nos2(18126)
rat ... Grin2a(24409), Nos1(24598)

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Application

Nω-Nitro-L-arginine has been used:
  • as nitric oxide synthase (NOS) inhibitor, to measure the release of nitric oxide (NO) derivatives in cytochrome c reduction assay
  • to pretreat fiber bundles for contractile studies
  • as NOS inhibitor to characterize the generation of NO in Taxus yunnanensis cells
  • as an irreversible inhibitor of the neuronal NO synthase (nNOS) to preincubate swimbladder preparations

Packaging

5, 25 g in poly bottle
1 g in poly tube

Biochem/physiol Actions

Nω-Nitro-L-arginine/L-NNA helps to reduce the levels of cortical hyperemia and brain cGMP occurring due to hypercapnia.
Irreversible inhibitor of constitutive nitric oxide synthase (nNOS) and a reversible inhibitor of inducible nitric oxide synthase (iNOS).

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.
This compound is featured on the Nitric Oxide Synthases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Nitric oxide modulates excitation-contraction coupling in the diaphragm
Reid M B, et al.
Comparative Biochemistry and Physiology. Part A, Molecular & Integrative Physiology, 119(1), 211-218 (1998)
L-NNA decreases cortical hyperemia and brain cGMP levels following CO2 inhalation in Sprague-Dawley rats
Irikura K, et al.
The American Journal of Physiology, 267(2), H837-H843 (1994)
Cyclic GMP is a second messenger by which nitric oxide inhibits diaphragm contraction
Abraham R Z, et al.
Comparative Biochemistry and Physiology. Part A, Molecular & Integrative Physiology, 119(1), 177-183 (1998)
Comp Biochem Physiol A Mol Integr Physiol
Schwerte T, et al.
The Journal of Experimental Biology, 202(8), 1005-1013 (1999)
Tiziana Sinagra et al.
Biochemical pharmacology, 85(4), 551-559 (2012-12-01)
Thiazolidinediones (also referred to as glitazones), agonists for Peroxisome Proliferator-Activated Receptor gamma (PPARγ), are used for treating type 2 diabetes mellitus, where they decrease insulin resistance and cardiovascular risk. Compounds bearing the thiazolidinedione structure have also been shown to inhibit...

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