Asymmetric dimethylarginine

Asymmetric dimethylarginine
Names
	IUPAC name 2-Amino-5-[[amino(dimethylamino)methylidene]amino]pentanoic acid
	Other names N(G),N(G′)-Dimethylarginine
Identifiers
CAS Number	30315-93-6 S ;
3D model (JSmol)	Interactive image;
3DMet	B00612;
Beilstein Reference	2261521 S
ChEBI	CHEBI:17929 ;
ChEMBL	ChEMBL457530 ;
ChemSpider	487 ; 16743930 R ; 110375 S ;
DrugBank	DB01686 ;
KEGG	C03626 ;
MeSH	N,N-dimethylarginine
PubChem CID	501; 17753937 R; 123831 S;
UNII	63CV1GEK3Y ;
CompTox Dashboard (EPA)	DTXSID401017725 DTXSID6036758, DTXSID401017725 ;
	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) Key: YDGMGEXADBMOMJ-UHFFFAOYSA-N ;
	SMILES CN(C)C(=N)NCCC[C@H](N)C(=O)O;
Properties
Chemical formula	C8H18N4O2
Molar mass	202.258 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). verify (what is ?) 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.