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Creatine ethyl ester

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Creatine ethyl ester
Names
IUPAC name Ethyl N-(aminoiminomethyl)-N-methylglycine
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H13N3O2/c1-3-11-5(10)4-9(2)6(7)8/h3-4H2,1-2H3,(H3,7,8)Key: UFUWQSYRGLMLKP-UHFFFAOYSA-N
  • InChI=1/C6H13N3O2/c1-3-11-5(10)4-9(2)6(7)8/h3-4H2,1-2H3,(H3,7,8)Key: UFUWQSYRGLMLKP-UHFFFAOYAK
SMILES
  • NC(N(C)CC(OCC)=O)=N
  • O=C(OCC)CN(C(=)N)C
Properties
Chemical formula C6H13N3O2
Molar mass 159.189 g·mol
Acidity (pKa) 2.67, 11.2, 6
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Creatine ethyl ester, also known as creatine ester, cre-ester and CEE, is a substance sold as an aid for athletic performance and for muscle development in bodybuilding. It is an ethyl ester derivative of creatine, from which it is made. In the body, CEE is converted back into creatine. CEE is said to have a much better absorption rate and a longer half-life in the body than regular creatine monohydrate, because it is slightly more lipophilic. It is also proposed to bypass the creatine transporter, thereby increasing skeletal muscle uptake of creatine and leading to an increased ability to regenerate ATP. However, in a published study comparing the two, CEE was not as effective at increasing serum and muscle creatine levels or in improving body composition, muscle mass, strength, and power. The same study found CEE to be comparable to placebo.

Research published in 2013 found that creatine ethyl ester is likely to be no better than taking creatine.

As a supplement, the compound was developed, patented and licensed through UNeMed, the technology transfer entity of the University of Nebraska Medical Center, and is sold under numerous brand names.

See also

References

  1. ^ Spillane, Mike; Schoch, Ryan; Cooke, Matt; Harvey, Travis; Greenwood, Mike; Kreider, Richard; Willoughby, Darryn S (2009). "The effects of creatine ethyl ester supplementation combined with heavy resistance training on body composition, muscle performance, and serum and muscle creatine levels". Journal of the International Society of Sports Nutrition. 6: 6. doi:10.1186/1550-2783-6-6. PMC 2649889. PMID 19228401.{{cite journal}}: CS1 maint: unflagged free DOI (link)
  2. Katseres, Nicholas S.; Reading, David W.; Shayya, Luay; Dicesare, John C.; Purser, Gordon H. (2009). "Non-enzymatic hydrolysis of creatine ethyl ester". Biochemical and Biophysical Research Communications. 386 (2): 363–7. doi:10.1016/j.bbrc.2009.06.037. PMID 19524547.
  3. "Analysis of Creatine Ethyl Ester: TU researchers bust myth on popular nutritional supplement". University of Tulsa.
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