N,N-DIMETHYLARGININE

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29101459 | https://www.ncbi.nlm.nih.gov/pubmed/28945167 | https://www.ncbi.nlm.nih.gov/pubmed/29235018

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.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Nitric oxide sythases; iNOS & nNOS 2 Target ID: CHEMBL2096621 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16028689	Inhibitor 8504
Nitric-oxide synthase (endothelial and brain) 1 Target ID: CHEMBL2111405 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16028689	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Fetal growth restriction 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29235018	Diagnostic	Natural Metabolite	Unknown Approved Use Unknown
Peripheral arterial disease 22 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28945167	Diagnostic	Natural Metabolite	Unknown Approved Use Unknown
Intracerebral hemorrhage 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29237474	Diagnostic	Natural Metabolite	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Endothelium-derived vasoactive factors and hypertension: possible roles in pathogenesis and as treatment targets.	2010-08	20532699
The serum protein and lipid oxidation marker levels in Alzheimer's disease and effects of cholinesterase inhibitors and antipsychotic drugs therapy.	2010-08	20043811
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.	2010-08	19729464
The Role of Asymmetric Dimethylarginine (ADMA) in Endothelial Dysfunction and Cardiovascular Disease.	2010-05	21532773
Advanced glycation end-products induce vascular dysfunction via resistance to nitric oxide and suppression of endothelial nitric oxide synthase.	2010-04	20186099
ADMA injures the glomerular filtration barrier: role of nitric oxide and superoxide.	2009-06	19297451
Asymmetric dimethylarginine (ADMA) and endothelial dysfunction: implications for atherogenesis.	2009-05	19488614
Plasma asymmetric dimethylarginine is related to anticitrullinated protein antibodies in rheumatoid arthritis of short duration.	2009-03	19217445
From arginine methylation to ADMA: a novel mechanism with therapeutic potential in chronic lung diseases.	2009-01-29	19178698
Telmisartan decreases plasma levels of asymmetrical dimethyl-L-arginine and improves lipid and glucose metabolism and vascular function.	2009-01	19246848
Long-term treatment with sulfhydryl angiotensin-converting enzyme inhibition reduces carotid intima-media thickening and improves the nitric oxide/oxidative stress pathways in newly diagnosed patients with mild to moderate primary hypertension.	2008-12	19033012
Sodium, hypertension, and an explanation of the "lag phenomenon" in hemodialysis patients.	2008-10	19090863
L-arginine analogs--inactive markers or active agents in atherogenesis?	2008-10	18855643
Oleanolic acid induces relaxation and calcium-independent release of endothelium-derived nitric oxide.	2008-10	18622409
A new selective pre-column ninhydrin-based derivatization for a RP-HPLC determination of plasma asymmetric dimethyl-L-arginine (ADMA) by fluorescence detection.	2008-05	18043861
Synthetic approaches to N(delta)-methylated L-arginine, N(omega)-hydroxy-L-arginine, L-citrulline, and N(delta)-cyano-L-ornithine.	2008-02-01	18179234
The relationship between plasma asymmetrical dimethyl-L-arginine and inflammation and adhesion molecule levels in subjects with normal, impaired, and diabetic glucose tolerance.	2008-01	18078867
Asymmetrical dimethylarginine, inflammatory and metabolic parameters in women with polycystic ovary syndrome before and after metformin treatment.	2008-01	17986642
Association of an endogenous inhibitor of nitric oxide synthase with cerebral vasospasm in patients with aneurysmal subarachnoid hemorrhage.	2007-11	17977265
Arginase: a critical regulator of nitric oxide synthesis and vascular function.	2007-09	17645639
Plasma adhesion and inflammation markers: asymmetrical dimethyl-L-arginine and secretory phospholipase A2 concentrations before and after laparoscopic gastric banding in morbidly obese patients.	2007-05	17658029
Elevated plasma asymmetric dimethyl-L-arginine levels are linked to endothelial progenitor cell depletion and carotid atherosclerosis in rheumatoid arthritis.	2007-03	17328055
Elevated plasma asymmetric dimethyl-L-arginine in a patient with Gordon syndrome.	2007-01	16998213
Homocysteine and asymmetric dimethylarginine (ADMA): biochemically linked but differently related to vascular disease in chronic kidney disease.	2007	17937610
Cross-talk between the kidney and the cardiovascular system.	2006-08	16825329
High glucose-mediated imbalance of nitric oxide synthase and dimethylarginine dimethylaminohydrolase expression in endothelial cells.	2006-02	16472125
Relations between plasma asymmetric dimethylarginine (ADMA) and risk factors for coronary disease.	2006-02	15939423
Effects of ADMA upon gene expression: an insight into the pathophysiological significance of raised plasma ADMA.	2005-10	16190779
Determination of methylated arginines by column-switching high-performance liquid chromatography-fluorescence detection.	2005-10	16172667
A selective estrogen receptor modulator, tamoxifen, and membrane fluidity of erythrocytes in normotensive and hypertensive postmenopausal women: an electron paramagnetic resonance investigation.	2005-08	16109320
Asymmetric dimethyl-L-arginine (ADMA): a possible link between homocyst(e)ine and endothelial dysfunction.	2005-02	15720202
Nitric oxide regulation system in degenerative lumbar disease.	2005	16119611
Elevation of asymmetric dimethylarginine (ADMA) in patients developing hepatic failure after major hepatectomy.	2004-12-01	15568284
Capillary electrophoretic and micellar electrokinetic separations of asymmetric dimethyl-L-arginine and structurally related amino acids: quantitation in human plasma.	2004-12	15638156
A calcium channel blocker, benidipine, improves cell membrane fluidity in human subjects via a nitric oxide-dependent mechanism. An electron paramagnetic resonance investigation.	2004-12	15607621
Weight loss reduces circulating asymmetrical dimethylarginine concentrations in morbidly obese women.	2004-12	15579789
The transplanted liver graft is capable of clearing asymmetric dimethylarginine.	2004-12	15558588
Association between cerebrospinal fluid levels of asymmetric dimethyl-L-arginine, an endogenous inhibitor of endothelial nitric oxide synthase, and cerebral vasospasm in a primate model of subarachnoid hemorrhage.	2004-11	15543672
Plasma concentrations of nitric oxide and asymmetric dimethylarginine in human alcoholic cirrhosis.	2004-07	15246208
Sulfhydryl angiotensin-converting enzyme inhibition induces sustained reduction of systemic oxidative stress and improves the nitric oxide pathway in patients with essential hypertension.	2004-07	15215814
Determination of l-arginine and NG, NG - and NG, NG' -dimethyl-L-arginine in plasma by liquid chromatography as AccQ-Fluor fluorescent derivatives.	2004-06-15	15135108
Elevated plasma asymmetric dimethylarginine as a marker of cardiovascular morbidity in early diabetic nephropathy in type 1 diabetes.	2004-03	14988299
Atherosclerosis in dialyzed patients.	2004	14732809
Effect of oestrone on membrane fluidity of erythrocytes is mediated by a nitric oxide-dependent pathway: An electron paramagnetic resonance study.	2002-11	12366388
Circulating concentrations of asymmetrical dimethyl-L-arginine are increased in women with previous gestational diabetes.	2002-10	12378377
Leptin improves membrane fluidity of erythrocytes in humans via a nitric oxide-dependent mechanism--an electron paramagnetic resonance investigation.	2002-09-27	12270147
Synergistic role of progesterone and nitric oxide in the regulation of membrane fluidity of erythrocytes in humans: an electron paramagnetic resonance investigation.	2002-08	12160193
Acute administration of L-arginine does not improve arterial endothelial function in chronic renal failure.	2001-12	11737605
Dialysis improves endothelial function in humans.	2001-09	11522865
Electron paramagnetic resonance investigation on modulatory effect of 17beta-estradiol on membrane fluidity of erythrocytes in postmenopausal women.	2001-08	11498458

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

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 `Mon Mar 31 19:54:06 GMT 2025` Edited by `admin` on `Mon Mar 31 19:54:06 GMT 2025`
Record UNII	63CV1GEK3Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

N,N-DIMETHYLARGININE

Systematic Name

English

ADMA

Preferred 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

ASYMMETRIC DIMETHYLARGININE

Common Name

English

Classification Tree Code System Code

LOINC

79635-9