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M7033

Sigma-Aldrich

NG-Methyl-L-arginine acetate salt

≥98% (TLC)

Synonym(s):

Nω-Methyl-L-arginine acetate salt, L-NMMA, N5-(Methylamidino)-L-ornithine acetate salt, NG-Monomethyl-L-arginine acetate salt

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About This Item

Empirical Formula (Hill Notation):
C7H16N4O2 · C2H4O2
CAS Number:
53308-83-1
Molecular Weight:
248.28
Beilstein:
6674255
MDL number:
MFCD00069311
UNSPSC Code:
12352209
PubChem Substance ID:
24278043
NACRES:
NA.77

Quality Level

200

Assay

≥98% (TLC)

form

powder

solubility

water: 49.00-51.00 mg/mL, clear to very slightly hazy, colorless to faintly yellow

SMILES string

CC(O)=O.CNC(=N)NCCC[C@H](N)C(O)=O

InChI

1S/C7H16N4O2.C2H4O2/c1-10-7(9)11-4-2-3-5(8)6(12)13;1-2(3)4/h5H,2-4,8H2,1H3,(H,12,13)(H3,9,10,11);1H3,(H,3,4)/t5-;/m0./s1

InChI key

IKPNWIGTWUZCKM-JEDNCBNOSA-N

Gene Information

human ... NOS1(4842) , NOS2(4843) , NOS3(4846)
mouse ... Nos2(18126)
rat ... Nos1(24598) , Nos2(24599)

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Application

NG-Methyl-L-arginine acetate salt has been used:
  • as an inhibitor of nitric oxide synthase (NOS) in wound healing studies in injured mice
  • as an inhibitor of nitric oxide synthase (NOS) to study nitric oxide (NO) immunosuppressive effect of murine stem cells
  • as an inhibitor to monitor NO levels in hemocytes respiratory burst assay

Biochem/physiol Actions

NG-Methyl-L-arginine is an inhibitor of nitric oxide synthase in neurons, endothelial cells, and macrophages. It inhibits endothelium-derived relaxing factor and promotes contraction in pulmonary artery and vein. It stereo selectively inhibits the generation of nitric oxide (NO) from arginine. It promotes epinephrine and glucose levels, contributing to hyperglycemia in central nervous system.

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Safa Al Therwani et al.
BMC nephrology, 18(1), 86-86 (2017-03-16)
Tolvaptan is a selective vasopressin receptor antagonist. Nitric Oxide (NO) promotes renal water and sodium excretion, but the effect is unknown in the nephron's principal cells. In a dose-response study, we measured the effect of tolvaptan on renal handling of
NG-methyl-L-arginine causes endothelium-dependent contraction and inhibition of cyclic GMP formation in artery and vein.
Gold ME, et al.
Proceedings of the National Academy of Sciences of the USA, 87(12), 4430-4434 (1990)
Jonna Idh et al.
PloS one, 12(7), e0181221-e0181221 (2017-07-14)
Drugs such as isoniazid (INH) and pretomanid (PRT), used against Mycobacterium tuberculosis are active partly through generation of reactive nitrogen species (RNS). The aim of this study was to explore variability in intracellular susceptibility to nitric oxide (NO) in clinical
NG-methyl-L-arginine functions as an alternate substrate and mechanism-based inhibitor of nitric oxide synthase
Olken NM and Marletta MA
Biochemistry, 32(37), 9677-9685 (1993)
NG-methyl-L-arginine, an inhibitor of nitric oxide synthase, affects the central nervous system to produce peripheral hyperglycemia in conscious rats
Uemura K, et al.
Neuroendocrinology, 66(2), 136-144 (1997)
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