Glycocyamine

Glycocyamine
Names
	IUPAC name N-Carbamimidoylglycine
	Systematic IUPAC name 2-(Diaminomethylideneamino)acetic acid
	Other names 2-Guanidinoacetic acid
Identifiers
CAS Number	352-97-6 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1759179
ChEBI	CHEBI:16344 ;
ChEMBL	ChEMBL281593 ;
ChemSpider	743 ;
DrugBank	DB02751 ;
ECHA InfoCard	100.005.936
EC Number	206-529-5;
KEGG	C00581 ;
MeSH	glycocyamine
PubChem CID	763;
UNII	GO52O1A04E ;
CompTox Dashboard (EPA)	DTXSID50861885 ;
	InChI InChI=1S/C3H7N3O2/c4-3(5)6-1-2(7)8/h1H2,(H,7,8)(H4,4,5,6) Key: BPMFZUMJYQTVII-UHFFFAOYSA-N ;
	SMILES NC(=N)NCC(O)=O;
Properties
Chemical formula	C3H7N3O2
Molar mass	117.108 g·mol−1
Appearance	White crystals
Odor	Odourless
Melting point	300 °C (572 °F; 573 K)
log P	−1.11
Acidity (pKa)	3.414
Basicity (pKb)	10.583
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P305+P351+P338
Related compounds
Related alkanoic acids	Sarcosine; Dimethylglycine; Creatine; N-Methyl-D-aspartic acid; beta-Methylamino-L-alanine; Guanidinopropionic acid;
Related compounds	Dimethylacetamide
	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

Glycocyamine (or guanidinoacetate) is a metabolite of glycine in which the amino group has been converted into a guanidine by guanylation (transfer of a guanidine group from arginine). In vertebrate organism it is then transformed into creatine by methylation.

Glycocyamine is used as a supplement and as a feed additive in poultry farming. However, the metabolism of creatine from glycocyamine in the liver causes a depletion of methyl groups. This causes homocysteine levels to rise, which has been shown to produce cardiovascular and skeletal problems. Glycocyamine plays a role in the metabolism of the amino acids serine, threonine, and proline.