N5751

N_ω-Nitro-L-arginine methyl ester hydrochloride

Name: <I>N</I><SUB>ω</SUB>-Nitro-<SC>L</SC>-arginine methyl ester hydrochloride
Brand: SIGMA

≥97% (TLC), powder, nitric oxide production inhibitor

Synonym(s):

L-NAME HCl, L-NAME hydrochloride

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All Photos(5)

About This Item

Empirical Formula (Hill Notation):

C₇H₁₅N₅O₄ · HCl

CAS Number:

51298-62-5

Molecular Weight:

269.69

NACRES:

NA.77

PubChem Substance ID:

24278011

UNSPSC Code:

12352209

EC Number:

257-116-1

MDL number:

MFCD00039052

Beilstein/REAXYS Number:

3744166

Product Name

N_ω-Nitro-L-arginine methyl ester hydrochloride, ≥97% (TLC), powder

InChI key

QBNXAGZYLSRPJK-JEDNCBNOSA-N

InChI

1S/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/t5-;/m0./s1

SMILES string

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

biological source

synthetic

assay

≥97% (TLC)

form

powder

color

white to off-white

mp

132 °C

solubility

H₂O: 50 mg/mL

storage temp.

−20°C

Quality Level

200

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Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

Application

Nω-Nitro-L-arginine methyl ester hydrochloride has been used:

to study the effects of brain-derived neurotrophic factor against neurotoxicity in rat cortical neurons
to study its effect on far-infrared (FIR) enhanced microcirculation of rat skin
to study its effect on leptin-induced regulation of myokine fibronectin type III domain containing five/irisin in murine myocytes and fat cells
to study its effect on the levels of arginine vasopressin and neuronal nitric oxide synthase mRNA levels in hypothalamic paraventricular nucleus and supraoptic nucleus of rat

Biochem/physiol Actions

Arginine analog that inhibits NO production.

General description

Nω-Nitro-L-argininemethyl ester hydrochloride or L -NAME HCl, ananalog of arginine, inhibits NO production. It has multiple effects on thevascular system. Inhibits relaxation induced by acetylcholine and induces anincrease in arterial blood pressure. Abolishes lecithinized superoxidedismutase induced vasodilation when used to pretreat aortic ring preparationsof mice. Induces leukocyte adhesion and increases microvascular fluid andprotein fluxes and permeability. It has also been used in many studies oflearning and memory.

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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Nitric oxide modulates microvascular permeability.

P Kubes et al.

The American journal of physiology, 262(2 Pt 2), H611-H615 (1992-02-01)

We recently demonstrated that inhibitors of nitric oxide (NO) production cause a dramatic increase in leukocyte adherence and emigration in postcapillary venules. The objective of this study was to assess whether inhibition of NO production leads to vascular protein leakage

Nitric oxide synthase inhibitors impair reference memory formation in a radial arm maze task in rats.

L B Zou et al.

Neuropharmacology, 37(3), 323-330 (1998-07-29)

We investigated the role of nitric oxide (NO) in learning and memory formation in a radial maze test, by using the NO synthase (NOS) inhibitors, NG-nitro-L-arginine methyl ester (L-NAME) and 7-nitroindazole (7-NI), and an NO precursor, L-arginine. Rats were trained

Shear stress regulates endothelial microparticle release.

Anne-Clémence Vion et al.

Circulation research, 112(10), 1323-1333 (2013-03-29)

Endothelial activation and apoptosis release membrane-shed microparticles (EMP) that emerge as important biological effectors. Because laminar shear stress (SS) is a major physiological regulator of endothelial survival, we tested the hypothesis that SS regulates EMP release. EMP levels were quantified

Rats with adenine-induced chronic renal failure develop low-renin, salt-sensitive hypertension and increased aortic stiffness.

Lisa Nguy et al.

American journal of physiology. Regulatory, integrative and comparative physiology, 304(9), R744-R752 (2013-03-22)

Rats with adenine-induced chronic renal failure (A-CRF) develop metabolic and cardiovascular abnormalities resembling those in patients with chronic kidney disease. The aim of this study was to investigate the mechanisms of hypertension in this model and to assess aortic stiffness

Protective effects of brain-derived neurotrophic factor against neurotoxicity of 3-nitropropionic acid in rat cortical neurons.

Wu CL, et al.

Neurotoxicology, 30(4), 718-726 (2009)

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