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Creatine information


Creatine
Skeletal formula of neutral form of creatine
Skeletal formula of neutral form of creatine
Skeletal formula of one of zwitterionic forms of creatine
Skeletal formula of one of the zwitterionic forms of creatine
Ball and stick model 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 checkY
3D model (JSmol)
  • Interactive image
3DMet
  • B00084
Beilstein Reference
907175
ChEBI
  • CHEBI:16919 checkY
ChEMBL
  • ChEMBL283800 checkY
ChemSpider
  • 566 checkY
DrugBank
  • DB00148 checkY
ECHA InfoCard 100.000.278 Edit this at Wikidata
EC Number
  • 200-306-6
Gmelin Reference
240513
KEGG
  • C00300 checkY
MeSH Creatine
PubChem CID
  • 586
RTECS number
  • MB7706000
UNII
  • MU72812GK0 checkY
CompTox Dashboard (EPA)
  • DTXSID1040451 Edit this at Wikidata
InChI
  • InChI=1S/C4H9N3O2/c1-7(4(5)6)2-3(8)9/h2H2,1H3,(H3,5,6)(H,8,9) checkY
    Key: CVSVTCORWBXHQV-UHFFFAOYSA-N checkY
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 (S298)
189.5 J K−1 mol−1
Std enthalpy of
formation fH298)
−538.06–−536.30 kJ mol−1
Std enthalpy of
combustion cH298)
−2.3239–−2.3223 MJ mol−1
Pharmacology
ATC code
C01EB06 (WHO)
Pharmacokinetics:
Biological half-life
3 hours
Hazards
GHS labelling:
Pictograms
GHS07: Exclamation mark
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).
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Infobox references

Creatine (/ˈkrətn/ or /ˈkrətɪn/)[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]

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

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Creatine

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Creatine (/ˈkriːətiːn/ or /ˈkriːətɪn/) is an organic compound with the nominal formula (H2N)(HN)CN(CH3)CH2CO2H. It exists in various tautomers in solutions...

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Creatine kinase

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Creatine kinase (CK), also known as creatine phosphokinase (CPK) or phosphocreatine kinase, is an enzyme (EC 2.7.3.2) expressed by various tissues and...

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Phosphocreatine

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Phosphocreatine, also known as creatine phosphate (CP) or PCr (Pcr), is a phosphorylated form of creatine that serves as a rapidly mobilizable reserve...

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Creatinine

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-niːn/; from Ancient Greek: κρέας (kréas) 'flesh') is a breakdown product of creatine phosphate from muscle and protein metabolism. It is released at a constant...

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Creatine phosphate shuttle

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The creatine phosphate shuttle is an intracellular energy shuttle which facilitates transport of high energy phosphate from muscle cell mitochondria to...

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Bang Energy

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it contained 'Super Creatine'. The suit found that 'Super Creatine' was not actually creatine, and did not raise the body's creatine levels. The trademark...

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Creatine methyl ester

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Creatine methyl ester is the methyl ester derivative of the amino acid creatine. It can be prepared by the esterification of creatine with methanol. Creatine...

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Cerebral creatine deficiency

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Cerebral creatine deficiencies are a small group of inherited disorders that result from defects in creatine biosynthesis and utilization. Commonly affected...

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Creatine transporter defect

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Creatine transporter deficiency (CTD) is an inborn error of creatine metabolism in which creatine is not properly transported to the brain and muscles...

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Twinlab

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Twinlab Consolidated Corporation is an American company which manufactures and markets vitamins, minerals, and bodybuilding supplements. Twinlab is based...

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Bodybuilding supplement

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branched-chain amino acids (BCAA), glutamine, arginine, essential fatty acids, creatine, HMB, whey protein, ZMA, and weight loss products. Supplements are sold...

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Phosphagen

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use creatine. Creatine phosphate (CP), or phosphocreatine (PCr), is made from ATP by the enzyme creatine kinase in a reversible reaction: Creatine + ATP...

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Rhabdomyolysis

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no red blood cells when examined with a microscope. Blood tests show a creatine kinase activity greater than 1,000 U/L, with severe disease being above...

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Guanidinoacetate methyltransferase deficiency

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recessive cerebral creatine deficiency that primarily affects the nervous system and muscles. It is the first described disorder of creatine metabolism, and...

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Isozyme

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Isoenzymes of creatine phosphokinase: Creatine kinase (CK) or creatine phosphokinase (CPK) catalyses the interconversion of phospho creatine to creatine . CPK...

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Creatinase

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chemical reaction creatine + H2O ⇌ {\displaystyle \rightleftharpoons } sarcosine + urea Thus, the two substrates of this enzyme are creatine and H2O, whereas...

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Loading

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athletes to maximize the storage of glycogen in the muscles Creatine loading, a phase of use of creatine supplements Vocal loading, the stress inflicted on the...

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Bioenergetic systems

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muscle contraction by ATPase) H+ + ADP + CP → ATP + Creatine (Mg2+ assisted, catalyzed by creatine kinase, ATP is used again in the above reaction for...

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Beef

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like any other meat (pork, fish, veal, lamb etc.), is a source of creatine. Creatine is converted to creatinine during cooking. Consumption of red meat...

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