Creatine

Creatine
	; Skeletal formula of neutral form of creatine
	; Skeletal formula of one of the zwitterionic forms of creatine
	; Ball and stick model of one zwitterionic form of creatine
Names
	Systematic IUPAC name 2-[Carbamimidoyl(methyl)amino]acetic acid
	Other names N-Carbamimidoyl-N-methylglycine; Methylguanidoacetic acid; N-amidinosarcosine
Identifiers
CAS Number	57-00-1 ;
3D model (JSmol)	Interactive image;
3DMet	B00084;
Beilstein Reference	907175
ChEBI	CHEBI:16919 ;
ChEMBL	ChEMBL283800 ;
ChemSpider	566 ;
DrugBank	DB00148 ;
ECHA InfoCard	100.000.278
EC Number	200-306-6;
Gmelin Reference	240513
KEGG	C00300 ;
MeSH	Creatine
PubChem CID	586;
RTECS number	MB7706000;
UNII	MU72812GK0 ;
CompTox Dashboard (EPA)	DTXSID1040451 ;
	InChI InChI=1S/C4H9N3O2/c1-7(4(5)6)2-3(8)9/h2H2,1H3,(H3,5,6)(H,8,9) Key: CVSVTCORWBXHQV-UHFFFAOYSA-N ;
	SMILES CN(CC(=O)O)C(=N)N;
Properties
Chemical formula	C4H9N3O2
Molar mass	131.135 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
Heat capacity (C)	171.1 J K−1 mol−1 (at 23.2 °C)
Std molar; entropy (S⦵298)	189.5 J K−1 mol−1
Std enthalpy of; formation (ΔfH⦵298)	−538.06–−536.30 kJ mol−1
Std enthalpy of; combustion (ΔcH⦵298)	−2.3239–−2.3223 MJ mol−1
Pharmacology
ATC code	C01EB06 (WHO)
	Pharmacokinetics:
Biological half-life	3 hours
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; 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). verify (what is ?) Infobox references

Creatine (/ˈkriːətiːn/ or /ˈkriːətɪn/)^[1] is an organic compound with the nominal formula (H₂N)(HN)CN(CH₃)CH₂CO₂H. It exists in various tautomers in solutions (among which are neutral form and various zwitterionic forms). Creatine is found in vertebrates where it facilitates recycling of adenosine triphosphate (ATP), primarily in muscle and brain tissue. Recycling is achieved by converting adenosine diphosphate (ADP) back to ATP via donation of phosphate groups. Creatine also acts as a buffer.^[2]

^ Stout JR, Antonio J, Kalman E, eds. (2008). Essentials of Creatine in Sports and Health. Humana. ISBN 978-1-59745-573-2.
^ Barcelos RP, Stefanello ST, Mauriz JL, Gonzalez-Gallego J, Soares FA (2016). "Creatine and the Liver: Metabolism and Possible Interactions". Mini Reviews in Medicinal Chemistry. 16 (1): 12–8. doi:10.2174/1389557515666150722102613. PMID 26202197. The process of creatine synthesis occurs in two steps, catalyzed by L-arginine:glycine amidinotransferase (AGAT) and guanidinoacetate N-methyltransferase (GAMT), which take place mainly in kidney and liver, respectively. This molecule plays an important energy/pH buffer function in tissues, and to guarantee the maintenance of its total body pool, the lost creatine must be replaced from diet or de novo synthesis.

[1] Stout JR, Antonio J, Kalman E, eds. (2008). Essentials of Creatine in Sports and Health. Humana. ISBN 978-1-59745-573-2.

[pmid26202197-2] Barcelos RP, Stefanello ST, Mauriz JL, Gonzalez-Gallego J, Soares FA (2016). "Creatine and the Liver: Metabolism and Possible Interactions". Mini Reviews in Medicinal Chemistry. 16 (1): 12–8. doi:10.2174/1389557515666150722102613. PMID 26202197. The process of creatine synthesis occurs in two steps, catalyzed by L-arginine:glycine amidinotransferase (AGAT) and guanidinoacetate N-methyltransferase (GAMT), which take place mainly in kidney and liver, respectively. This molecule plays an important energy/pH buffer function in tissues, and to guarantee the maintenance of its total body pool, the lost creatine must be replaced from diet or de novo synthesis.

[1]

[2]

Names
Skeletal formula of neutral form of creatine
Skeletal formula of one of the zwitterionic forms of creatine
Ball and stick model of one zwitterionic form of creatine
Systematic IUPAC name 2-[Carbamimidoyl(methyl)amino]acetic acid
Other names N-Carbamimidoyl-N-methylglycine; Methylguanidoacetic acid; N-amidinosarcosine
Identifiers
CAS Number	57-00-1^Y
3D model (JSmol)	Interactive image
3DMet	B00084
Beilstein Reference	907175
ChEBI	CHEBI:16919^Y
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 CID	586
RTECS number	MB7706000
UNII	MU72812GK0^Y
CompTox Dashboard (EPA)	DTXSID1040451
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 CN(CC(=O)O)C(=N)N
Properties
Chemical formula	C₄H₉N₃O₂
Molar mass	131.135 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 (pK_a)	3.429
Basicity (pK_b)	10.568
Isoelectric point	8.47
Thermochemistry
Heat capacity (C)	171.1 J K⁻¹ mol⁻¹ (at 23.2 °C)
Std molar entropy (S^⦵₂₉₈)	189.5 J K⁻¹ mol⁻¹
Std enthalpy of formation (Δ_fH^⦵₂₉₈)	−538.06–−536.30 kJ mol⁻¹
Std enthalpy of combustion (Δ_cH^⦵₂₉₈)	−2.3239–−2.3223 MJ mol⁻¹
Pharmacology
ATC code	C01EB06 (WHO)
Pharmacokinetics:
Biological half-life	3 hours
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 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 verify (what is ^YN ?) Infobox references