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Creatine Synthesis: An Undergraduate Organic Chemistry Laboratory Experiment

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Andri L. Smith and Paula Tan

Department of Chemistry, Quinnipiac University, Hamden, CT 06518

J. Chem. Educ., 2006, 83 (11), p 1654

DOI: 10.1021/ed083p1654

Publication Date (Web): November 1, 2006

Section:

History, Education, and Documentation

Abstract

Students in introductory chemistry classes typically appreciate seeing the connection between course content and the "real world". For this reason, we have developed a synthesis of creatine monohydrate—a popular supplement used in sports requiring short bursts of energy—for introductory organic chemistry laboratory courses. Creatine monohydrate is easily synthesized from N-methylglycine (sarcosine) and cyanamide in the presence of salt and base. The crude product is purified by recrystallization and analyzed by thin-layer chromatography, melting point, and nuclear magnetic resonance spectroscopy. This synthesis illustrates the electrophilic nature of nitriles, as well as the nucleophilic nature of amines.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Feature):

The Microscale Laboratory

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Amines / Ammonium Compounds

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This article has been cited by 1 ACS Journal articles (1 most recent appear below).

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- Natural Product Total Synthesis in the Organic Laboratory: Total Synthesis of Caffeic Acid Phenethyl Ester (CAPE), A Potent 5-Lipoxygenase Inhibitor from Honeybee Hives
  Mohamed Touaibia and Michel Guay
  Journal of Chemical Education2011 88 (4), 473-475
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