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Hall of Fame or Shame?

The Chemistry of a Designer Drug


Author(s)

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 Areas

Ethics, Legal issues

Educational Level

Undergraduate lower division

Format

PDF

Type / Methods

Directed, Student Presentations

Language

English

Subject Headings

Organic Chemistry  |  


Date Posted

1/19/2016

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