N5751

Sigma-Aldrich

Nω-Nitro-L-arginine methyl ester hydrochloride

≥98% (TLC), powder

Synonym(s):
L-NAME hydrochloride
Empirical Formula (Hill Notation):
C7H15N5O4 · HCl
CAS Number:
Molecular Weight:
269.69
Beilstein/REAXYS Number:
3744166
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77
Pricing and availability is not currently available.

biological source

synthetic

assay

≥98% (TLC)

form

powder

color

white to off-white

mp

132 °C

solubility

H2O: 50 mg/mL

storage temp.

−20°C

SMILES string

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

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

InChI key

QBNXAGZYLSRPJK-JEDNCBNOSA-N

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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

Packaging

250 mg in poly bottle
1, 5, 10, 25 g in poly bottle

Biochem/physiol Actions

An analog of arginine that inhibits NO production. It has multiple effects on the vascular system. Inhibits relaxation induced by acetylcholine and induces an increase in arterial blood pressure. Abolishes lecithinized superoxide dismutase induced vasodilation when used to pretreat aortic ring preparations of mice. Induces leukocyte adhesion and increases microvascular fluid and protein fluxes and permeability. It has also been used in many studies of learning and memory.

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.

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

  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  4. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  5. What is the solution stability of Product N5751, L-NAME hydrochloride?

    Although we do not perform solution stability studies, one literature reference recommends keeping solutions on ice during the course of one day.

  6. How do I sterilize a prepared solution of Product N5751, L-NAME hydrochloride?

    Solutions of this product may be sterile-filtered.

  7. Is Product N5751, L-NAME hydrochloride, an inhibitor of Nitric Oxide Synthase (NOS)?

    L-NAME was described as a reversible, non-specific inhibitor of nitric oxide synthase by Khavandgar. S. et al., Pharmacol. Biochem. Behav., 74, 795 (2003).

  8. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

  9. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

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...
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...
Biological effect of far-infrared therapy on increasing skin microcirculation in rats
Yu SY, et al.
Photodermatology, Photoimmunology & Photomedicine, 22(2), 78-86 (2006)
Amanda E Boe et al.
Circulation, 128(21), 2318-2324 (2013-10-05)
Long-term inhibition of nitric oxide synthase by L-arginine analogues such as N(ω)-nitro-l-arginine methyl ester (L-NAME) has been shown to induce senescence in vitro and systemic hypertension and arteriosclerosis in vivo. We previously reported that plasminogen activator inhibitor-1 (PAI-1)-deficient mice (PAI-1(-/-))...
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...
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