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Chapter 5: Q.50 (page 208)

Draw the structure of (S)-citalopram, a drug used to treat depression and anxiety that is much more potent than its R enantiomer.

citalopram

Short Answer

Expert verified

The structure of the (S)-citalopram is as follows:

Step by step solution

01

The R and S isomers

The enantiomers are named R and S according to the spatial arrangement of the different groups attached to them.

The two enantiomers of a compound have the same physical properties.

02

The strucuture of (S)-citalopram

Citalopram is a drug used to treat depression and anxiety. The (S)-citalopram is more potent than its R isomer. Following is the structure of (S)-citalopram:

S isomer

The R isomer of citalopram has the following structure:

R isomer

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Most popular questions from this chapter

Draw in a plane of symmetry for each molecule.

a.

b.

c.

d.

Like carvone, the two enantiomers of celery ketone smell differently. The R enantiomer smells like celery leaves, whereas the S enantiomer smells like licorice. Draw each enantiomer and assign its odor.

The facts in Section 5.4A can be used to locate stereogenic centers in any molecule, no matter how complicated. Always look for carbons surrounded by four different groups. With this in mind, locate the four stereogenic centers in aliskiren, a drug introduced in 2007 for the treatment of hypertension.

Explain each statement by referring to compounds A-E.

a. A has a mirror image but no enantiomer.

b. B has an enantiomer and no diastereomer.

c. C has both an enantiomer and a diastereomer.

d. D has a diastereomer but no enantiomer.

e. E has a diastereomer but no enantiomer.

a. Locate the stereogenic centres in the ball-and-stick model of lisinopril, a drug used to treat high blood pressure.

b. Label each stereogenic centre as R or S.
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