Creatine

Creatine

Names
Systematic IUPAC name 2-[Carbamimidoyl(methyl)amino]acetic acid
Other names N-Carbamimidoyl-N-methylglycine; Methylguanidoacetic acid
Identifiers
CAS Number	57-00-1 Y
3D model (Jmol)	Interactive image Interactive image
3DMet	B00084
Beilstein Reference	907175
ChEBI	CHEBI:16919 N
ChEMBL	ChEMBL283800 Y
ChemSpider	566 Y
DrugBank	DB00148 Y
ECHA InfoCard	100.000.278
EC Number	200-306-6
Gmelin Reference	240513
KEGG	C00300 Y
MeSH	Creatine
PubChem	586
RTECS number	MB7706000
UNII	MU72812GK0 Y
InChI InChI=1S/C4H9N3O2/c1-7(4(5)6)2-3(8)9/h2H2,1H3,(H3,5,6)(H,8,9) Y Key: CVSVTCORWBXHQV-UHFFFAOYSA-N Y
SMILES C[n](Cc(:[o]):[oH]):c(:[nH]):[nH2] CN(CC(O)=O)C(N)=N
Properties
Chemical formula	C4H9N3O2
Molar mass	131.14 g·mol−1
Appearance	White crystals
Odor	Odourless
Melting point	255 °C (491 °F; 528 K)
Solubility in water	13.3 g L−1 (at 18 °C)
log P	−1.258
Acidity (pKa)	3.429
Basicity (pKb)	10.568
Isoelectric point	8.47
Thermochemistry
Specific heat capacity (C)	171.1 J K−1 mol−1 (at 23.2 °C)
Std molar entropy (So298)	189.5 J K−1 mol−1
Std enthalpy of formation (ΔfHo298)	−538.06–−536.30 kJ mol−1
Std enthalpy of combustion (ΔcHo298)	−2.3239–−2.3223 MJ mol−1
Pharmacology
ATC code	C01EB06 (WHO)
Pharmacokinetics:
Biological half-life	3 hours
Hazards
GHS pictograms
GHS signal word	WARNING
GHS hazard statements	H315, H319, H335
GHS precautionary statements	P261, P305+351+338
EU classification (DSD)	Xi
R-phrases	R36/37/38
S-phrases	S26, S36
Related compounds
Related alkanoic acids	Sarcosine Dimethylglycine Glycocyamine 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).
N  (what is YN ?)
Infobox references

Creatine (/ˈkriːətiːn/ or /ˈkriːətɪn/) is a nitrogenous organic acid that occurs naturally in vertebrates. Its main role is to facilitate recycling of adenosine triphosphate (ATP), the energy currency of the cell, primarily in muscle and brain tissue. This is achieved by recycling adenosine diphosphate (ADP) to ATP via donation of phosphate groups. Creatine also acts as a pH buffer in tissues.

Creatine synthesis primarily occurs in the liver and kidneys. On average, it is produced endogenously at an estimated rate of about 8.3 mmol or 1 gram per day in young adults. Creatine is also obtained through the diet at a rate of about 1 gram per day from an omnivorous diet. Most of the human body's total creatine and phosphocreatine stores are found in skeletal muscle, while the remainder is distributed in the blood, brain, and other tissues.

Creatine was identified in 1832 when Michel Eugène Chevreul isolated it from the basified water-extract of skeletal muscle. He later named the crystallized precipitate after the Greek word for meat, κρέας (kreas). In solution, creatine is in equilibrium with creatinine. Creatine is a derivative of the guanidinium cation.