Compound
with Two Chiral Centers
The stereoisomers of
2-methylamino-1-phenyl-1-propanol, commonly known as ephedrine and pseudoephedrine,
have two chiral centers. Both of these compounds are optically active, with
stereogenic centers at carbon 1 and carbon 2. These compounds originate from the
Chinese medicinal shrub Ma Huang (Ephedra
vulgaris). Both ephedrine and pseudoephedrine increase blood pressure and
act as bronchodilators. Ephedrine promotes modest short-term fat loss.
Pseudoephedrine is most often used to shrink swollen nasal mucous membrane,
thus it’s used as a decongestant. Pseudoephedrine also has stimulant
properties. Both ephedrine and pseudoephedrine are available behind the
counter.
Below are
the depictions of all four stereoisomers of 2-methylamino-1-phenyl-1-propanol:
References:
http://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/sterism3.htm
Hi McKenna!
ReplyDeleteThese compounds were a good choice! I remember from physiology class that they are both very important due to their uses in the treatment of certain health problems as you mentioned above. Once again, great post and thanks for sharing the information!
I have had personal experience with ephedrine and it is scary how much drugs can affect your mind and body. Good description and explanation of these molecules!
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