Ephedrine

Given that it's allergy season and many of us have been relying on Pseudophed to help ease our stuffy noses, I thought it was fitting to examine this popular drug for this months blog.

The IUPAC name for the popular drug Ephedrine is 2-methlyamino-1-phenylpropanol. Commonly used as a stimulant, appetite suppressant and nasal decongestant, Ephedrine has been in the drug market for many years. Ephedrine was first synthesized in 1885 by a Japanese chemist, industrially manufactured in China by the late 1920s and was initially used to treat asthma and bronchitis. In more recent years, the drug has been known for its ability to stimulate weight loss.

The drug is optically active, giving rise to two chiral centers and four stereoisomers. The enantiomer pair with the stereochemistry (1R, 2S) and (1S, 2R) pictured at the top of the photo below are Ephedrine and the enantionmer pair stereochemistry (1R, 2R) and (1S, 2S) pictured at the bottom of the photo below are Pseudoephedrine. 

Ephedrine can be synthesized from benzaldehyde by a condensation reaction followed by a reduction reaction and completed with crystallization, a process that extends well beyond the scope of what we have learned in this class.

Resources:
http://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/sterism3.htm
http://en.wikipedia.org/wiki/Ephedrine