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Details

Stereochemistry ABSOLUTE
Molecular Formula C8H18N4O2
Molecular Weight 202.2541
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of N,N-DIMETHYLARGININE

SMILES

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

InChI

InChIKey=YDGMGEXADBMOMJ-LURJTMIESA-N
InChI=1S/C8H18N4O2/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)/t6-/m0/s1

HIDE SMILES / InChI

Molecular Formula C8H18N4O2
Molecular Weight 202.2541
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

N, N – Dimethylarginine, more known as asymmetric dimethylarginine (ADMA), a naturally occurring chemical found in blood plasma. It is formed by methylation of arginine residues in proteins and released after proteolysis. ADMA is an endogenous inhibitor of all isoforms of nitric oxide synthase, the enzyme that synthesizes nitric oxide from arginine. Elevated plasma concentrations of ADMA are associated with hypertension and other risk factors for cardiovascular disease. It is known, that chronic kidney disease (CDK) is associated with increased risk of renal and cardiovascular events and it has been claimed that asymmetric dimethylarginine (ADMA) and symmetric dimethylarginine (SDMA), are contributing factors. Nevertheless, the recent comprehensive analysis of methylarginines in a cohort of patients with non-dialysis CKD have revealed, the potential pathophysiological role of SDMA in CKD progression and atherosclerotic cardiovascular disease among non-dialysis CKD patients. Thus SDMA predicts CKD progression and future atherosclerotic cardiovascular events more consistently than other methylarginines. In addition, was also shown, that the maternal plasma ADMA concentration is an important indicator of fetal growth restriction in women with impaired placental perfusion independent of NO.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Acute administration of L-arginine does not improve arterial endothelial function in chronic renal failure.
2001 Dec
Effect of oestrone on membrane fluidity of erythrocytes is mediated by a nitric oxide-dependent pathway: An electron paramagnetic resonance study.
2002 Nov
Sulfhydryl angiotensin-converting enzyme inhibition induces sustained reduction of systemic oxidative stress and improves the nitric oxide pathway in patients with essential hypertension.
2004 Jul
Nitric oxide regulation system in degenerative lumbar disease.
2005
A selective estrogen receptor modulator, tamoxifen, and membrane fluidity of erythrocytes in normotensive and hypertensive postmenopausal women: an electron paramagnetic resonance investigation.
2005 Aug
Effects of ADMA upon gene expression: an insight into the pathophysiological significance of raised plasma ADMA.
2005 Oct
Determination of methylated arginines by column-switching high-performance liquid chromatography-fluorescence detection.
2005 Oct
Cross-talk between the kidney and the cardiovascular system.
2006 Aug
High glucose-mediated imbalance of nitric oxide synthase and dimethylarginine dimethylaminohydrolase expression in endothelial cells.
2006 Feb
Elevated plasma asymmetric dimethyl-L-arginine in a patient with Gordon syndrome.
2007 Jan
Plasma adhesion and inflammation markers: asymmetrical dimethyl-L-arginine and secretory phospholipase A2 concentrations before and after laparoscopic gastric banding in morbidly obese patients.
2007 May
Synthetic approaches to N(delta)-methylated L-arginine, N(omega)-hydroxy-L-arginine, L-citrulline, and N(delta)-cyano-L-ornithine.
2008 Feb 1
Synergistic effects of asymmetrical dimethyl-L-arginine accumulation and endothelial progenitor cell deficiency on renal function decline during a 2-year follow-up in stable angina.
2010 Aug
The Role of Asymmetric Dimethylarginine (ADMA) in Endothelial Dysfunction and Cardiovascular Disease.
2010 May

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
Asymmetric dimethylarginine (N,N-DIMETHYLARGININE; ADMA) induces the mitochondrial translocation of endothelial nitric oxide synthase (eNOS) through the nitration-mediated activation of Akt1. The study was performed to elucidate the potential effect of ADMA on Akt1 phosphorylation and the mechanisms that are involved. Western blot analysis demonstrated that, although ADMA (10 μM, 2 h) does not change total Akt1 levels. Akt1 phosphorylation at T308 and S473 were significantly increased. It was also found that ADMA treatment significantly increased Akt1 translocation from cytosol to the plasma membrane, suggesting that upon ADMA stimulation, Akt1 was activated, at least in part, through recruitment to that plasma membrane.
Substance Class Chemical
Created
by admin
on Fri Dec 15 19:42:14 GMT 2023
Edited
by admin
on Fri Dec 15 19:42:14 GMT 2023
Record UNII
63CV1GEK3Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
N,N-DIMETHYLARGININE
Systematic Name English
OMEGA-N,OMEGA-N-DIMETHYL-L-ARGININE
Common Name English
DIMETHYL-L-ARGININE
Systematic Name English
L-ORNITHINE, N5-((DIMETHYLAMINO)IMINOMETHYL)-
Systematic Name English
L-NG,NG-DIMETHYLARGININE
Common Name English
ADMA
Common Name English
ASYMMETRIC DIMETHYLARGININE
Common Name English
Classification Tree Code System Code
LOINC 79635-9
Created by admin on Fri Dec 15 19:42:14 GMT 2023 , Edited by admin on Fri Dec 15 19:42:14 GMT 2023
NCI_THESAURUS C73539
Created by admin on Fri Dec 15 19:42:14 GMT 2023 , Edited by admin on Fri Dec 15 19:42:14 GMT 2023
LOINC 74363-3
Created by admin on Fri Dec 15 19:42:14 GMT 2023 , Edited by admin on Fri Dec 15 19:42:14 GMT 2023
LOINC 80981-4
Created by admin on Fri Dec 15 19:42:14 GMT 2023 , Edited by admin on Fri Dec 15 19:42:14 GMT 2023
Code System Code Type Description
MESH
C018524
Created by admin on Fri Dec 15 19:42:14 GMT 2023 , Edited by admin on Fri Dec 15 19:42:14 GMT 2023
PRIMARY
EPA CompTox
DTXSID401017725
Created by admin on Fri Dec 15 19:42:14 GMT 2023 , Edited by admin on Fri Dec 15 19:42:14 GMT 2023
PRIMARY
CAS
30315-93-6
Created by admin on Fri Dec 15 19:42:14 GMT 2023 , Edited by admin on Fri Dec 15 19:42:14 GMT 2023
PRIMARY
CHEBI
17929
Created by admin on Fri Dec 15 19:42:14 GMT 2023 , Edited by admin on Fri Dec 15 19:42:14 GMT 2023
PRIMARY
NCI_THESAURUS
C124264
Created by admin on Fri Dec 15 19:42:14 GMT 2023 , Edited by admin on Fri Dec 15 19:42:14 GMT 2023
PRIMARY NCIT
FDA UNII
63CV1GEK3Y
Created by admin on Fri Dec 15 19:42:14 GMT 2023 , Edited by admin on Fri Dec 15 19:42:14 GMT 2023
PRIMARY
DRUG BANK
DB01686
Created by admin on Fri Dec 15 19:42:14 GMT 2023 , Edited by admin on Fri Dec 15 19:42:14 GMT 2023
PRIMARY
PUBCHEM
123831
Created by admin on Fri Dec 15 19:42:14 GMT 2023 , Edited by admin on Fri Dec 15 19:42:14 GMT 2023
PRIMARY
WIKIPEDIA
ASYMMETRIC DIMETHYLARGININE
Created by admin on Fri Dec 15 19:42:14 GMT 2023 , Edited by admin on Fri Dec 15 19:42:14 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> METABOLITE
PLASMA