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D4268

Sigma-Aldrich

NG,NG-Dimethylarginine dihydrochloride

Synonym(s):

asym-Dimethylarginine, ADMA

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About This Item

Empirical Formula (Hill Notation):
C8H18N4O2 · 2HCl
CAS Number:
220805-22-1
Molecular Weight:
275.18
MDL number:
MFCD00270857
UNSPSC Code:
12352209
PubChem Substance ID:
24278027
NACRES:
NA.77

assay

≥98% (TLC)

Quality Level

200

form

powder

solubility

water: 50 mg/mL, clear, colorless

storage temp.

room temp

SMILES string

Cl[H].Cl[H].CN(C)C(=N)NCCC[C@H](N)C(O)=O

InChI

1S/C8H18N4O2.2ClH/c1-12(2)8(10)11-5-3-4-6(9)7(13)14;;/h6H,3-5,9H2,1-2H3,(H2,10,11)(H,13,14);2*1H/t6-;;/m0../s1

InChI key

SYLNVYJOPZWPJI-ILKKLZGPSA-N

Gene Information

human ... NOS1(4842) , NOS2(4843) , NOS2B(201288) , NOS2C(645740) , NOS3(4846)

General description

NG,NG-Dimethylarginine dihydrochloride is a methylated arginine derivative, which is produced by the liver. It is linked to liver cirrhosis, alcoholic hepatitis and acute liver failure (ALF).

Application

NG,NG- Dimethylarginine dihydrochloride has been used:
  • to study its effects on cardiovascular activities in rostral ventrolateral medulla (RVLM) in rats
  • as a standard for measuring L-arginine and dimethylarginines
  • to study its effects on hepatic deterioration

Biochem/physiol Actions

Reversible inhibitor of nitric oxide synthetase in vivo and in vitro.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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Marie Rodling Wahlström et al.
SpringerPlus, 3, 98-98 (2014-03-07)
A prospective, randomised, double-blinded, clinical trial was performed at a level 1 trauma centre to determine if a prostacyclin analogue, epoprostenol (Flolan®), could attenuate systemic inflammatory response in patients with severe traumatic brain injury (TBI). 46 patients with severe TBI
Kyoung Min Kim et al.
Cardiovascular diabetology, 16(1), 146-146 (2017-11-11)
The cardiovascular benefits of statins have been proven, but their effect on circulation in small vessels has not been examined fully. We investigated the effect of 20 mg rosuvastatin on biomarkers, including paraoxonase-1 (PON-1) and asymmetric dimethylarginine (ADMA), and on microvascular
Aleksandar Radujkovic et al.
Haematologica, 104(4), 827-834 (2018-12-06)
Increasing evidence suggests that endothelial cell distress is associated with mortality after allogeneic stem cell transplantation and acute graft-versus-host disease. Asymmetric dimethylarginine is an endogenous nitric oxide synthase inhibitor that induces endothelial cell dysfunction. We analyzed the impact of pre-transplant
José D Martins et al.
Journal of the American Heart Association, 8(7), e011536-e011536 (2019-04-02)
Background Optimally treated patients with coarctation of the aorta remain at risk for late vascular dysfunction. The effect of treatment modality on vascular function is unknown. The LOVE-COARCT (Long-term Outcomes and Vascular Evaluation After Successful Coarctation of the Aorta Treatment)
Tse-Min Lu et al.
Atherosclerosis, 254, 161-166 (2016-10-17)
Decreased nitric oxide (NO) bioavailability and increased oxidative stress may be involved in the pathogenesis of contrast-induced acute kidney injury (CI-AKI). The relationship between asymmetric dimethylarginine (ADMA), an endogenous NO synthase inhibitor, and CI-AKI is unknown. We measured plasma ADMA
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