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Hall of Fame or Shame?

The Chemistry of a Designer Drug



Co Authors:

Reinaldo Perez
Department of Chemistry and Biochemistry
Florida International University

Andres Arango
Department of Chemistry and Biochemistry
Florida International University

Kathleen S. Rein
Department of Chemistry and Biochemistry
Florida International University
reink@fiu.edu

Abstract:

This case study involves the structure elucidation of the designer steroid tetrahydrogestrinone or THG by the UCLA Olympic Analytical Laboratory. This steroid was allegedly synthesized by BALCO organic chemist Patrick Arnold and was allegedly used by the famous baseball player, Barry Bonds. Students will learn the logic of structure elucidation and the techniques used by chemists to determine molecular structure. Students are asked to make predictions with respect to the changes in the proton NMR upon conversion of gestrinone to tetrahydrogestrinone. The case was originally developed for use in an organic chemistry survey course for non-chemistry majors, but could also be used in a general/organic/biochemistry survey course or modified for use in an organic chemistry sequence. Two sets of questions are included; the first is appropriate for students who are able to interpret skeletal structures and have studied addition reactions to alkenes, including hydrogenations, while the second is more advanced. Students will need access to a 2004 paper by D.H. Catlin et al. published in Rapid Communications in Mass Spectrometry (not included in this case).

Objectives:
  • Demonstrate the central role that organic chemistry plays in many social issues.
  • Recognize the general structure of steroid hormones
  • Recognize the structural difference between male and female sex hormones.
  • Understand and explain the term anabolic.
  • Introduce the students to analytical methods of mass spectrometry and nuclear magnetic resonance.
  • Develop an understanding of the process and techniques chemists use to determine molecular structure.
Keywords: Steroids; structure determination; hydrogenation; silylation; designer drugs; Barry Bonds; mass spectrometry; nuclear magnetic resonance; tetrahydrogestrinone; THG; BALCO
Topical Area: Ethics, Legal issues
Educational Level: Undergraduate lower division
Formats: PDF
Type/Method: Directed, Student Presentations
Language: English
Subject Headings: Organic Chemistry  
Date Posted: 1/19/2016
Date Modified: 1/29/2016
Copyright: Copyright held by the National Center for Case Study Teaching in Science, University at Buffalo, State University of New York. Please see our usage guidelines, which outline our policy concerning permissible reproduction of this work.

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