Asymmetric dimethylarginine

Asymmetric dimethylarginine

Names
Other names 2-Amino-5-[(amino-dimethylaminomethylene)amino]pentanoic acid
Identifiers
CAS Number	30315-93-6 S Y
3D model (Jmol)	Interactive image Interactive image
3DMet	B00612
Beilstein Reference	2261521 S
ChEBI	CHEBI:17929 N
ChEMBL	ChEMBL457530 N
ChemSpider	487 N 16743930 R N 110375 S N
DrugBank	DB01686 Y
KEGG	C03626 N
MeSH	N,N-dimethylarginine
PubChem	501 17753937 R 123831 S
UNII	63CV1GEK3Y N
InChI 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) N Key: YDGMGEXADBMOMJ-UHFFFAOYSA-N N
SMILES C[n](C):c(:[nH]):[nH]CCCC(N)c(:[o]):[oH] CN(C)C(=N)NCCCC(N)C(O)=O
Properties
Chemical formula	C8H18N4O2
Molar mass	202.26 g·mol−1
log P	−0.716
Acidity (pKa)	2.497
Basicity (pKb)	11.500
Related compounds
Related alkanoic acids	Methylarginine N-Propyl-L-arginine
Related compounds	Buformin Acecarbromal
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Asymmetric dimethylarginine (ADMA) is a naturally occurring chemical found in blood plasma. It is a metabolic by-product of continual protein modification processes in the cytoplasm of all human cells. It is closely related to L-arginine, a conditionally essential amino acid. ADMA interferes with L-arginine in the production of nitric oxide (NO), a key chemical involved in normal endothelial function and, by extension, cardiovascular health.

Patrick Vallance and his London co-workers first noted the interference role for asymmetric dimethylarginine in the early 1990s. Today biochemical and clinical research continues into the role of ADMA in cardiovascular disease, diabetes mellitus, erectile dysfunction and certain forms of kidney disease.

Asymmetric dimethylarginine is created in protein methylation, a common mechanism of post-translational protein modification. This reaction is catalyzed by an enzyme set called S-adenosylmethionine protein N-methyltransferases (protein methylases I and II). The methyl groups transferred to create ADMA are derived from the methyl group donor S-adenosylmethionine, an intermediate in the metabolism of homocysteine. (Homocysteine is an important blood chemical because it is also a marker of cardiovascular disease). After synthesis, ADMA migrates into the extracellular space and thence into blood plasma. Asymmetric dimethylarginine is measured using high-performance liquid chromatography.