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Merck

N5501

Nω-Nitro-L-arginine

synthetic, ≥98% (TLC), Nitric oxide synthase inhibitor, powder

Synonym(s):

L-NNA, N5-(Nitroamidino)-L-2,5-diaminopentanoic acid, NG-NO2-L-Arg

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About This Item

Empirical Formula (Hill Notation):
C6H13N5O4
CAS Number:
2149-70-4
Molecular Weight:
219.20
NACRES:
NA.77
PubChem Substance ID:
24278010
UNSPSC Code:
12352209
EC Number:
218-418-9
MDL number:
MFCD00007033
Beilstein/REAXYS Number:
1728914

Product Name

Nω-Nitro-L-arginine, ≥98% (TLC)

SMILES string

N[C@@H](CCCNC(=N)N[N+]([O-])=O)C(O)=O

InChI key

MRAUNPAHJZDYCK-BYPYZUCNSA-N

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

biological source

synthetic

assay

≥98% (TLC)

form

powder

mp

257 °C

solubility

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

Quality Level

200

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

Biochem/physiol Actions

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

Features and Benefits

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL9970
BCCH2076
BCCF9639
BCCD9665
1413116V

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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)
Helena Janols et al.
Journal of leukocyte biology, 96(5), 685-693 (2014-06-15)
The causative microorganisms dictate the type of MDSC generated in sepsis patients, and a large proportion of PMN-MDSCs in gram-positive sepsis includes immunosuppressive myeloid blasts. MDSCs constitute a heterogeneous population of immature myeloid cells that potently suppress immune responses. They
K D Keef et al.
The Journal of physiology, 591(6), 1489-1506 (2013-01-23)
There is evidence that vasoactive intestinal polypeptide (VIP) participates in inhibitory neuromuscular transmission (NMT) in the internal anal sphincter (IAS). However, specific details concerning VIP-ergic NMT are limited, largely because of difficulties in selectively blocking other inhibitory neural pathways. The
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