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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

The amino acid (S)-alanine has the physical characteristics listed under the structure.

a. What is the melting point of (R)-alanine?

b. How does the melting point of a racemic mixture of (R)- and (S)-alanine compare to the melting point of (S)-alanine?

c. What is the specific rotation of (R)-alanine, recorded under the same conditions as the reported rotation of (S)-alanine?

d. What is the optical rotation of a racemic mixture of (R)- and (S)-alanine?

e. Label each of the following as optically active or inactive: a solution of pure (S)-alanine; an equal mixture of (R)- and (S)-alanine; a solution that contains 75% (S)- and 25% (R)-alanine.

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.

What is the maximum number of stereoisomers possible for each compound?

a.

b.

c.

Artemisinin and mefloquine are widely used antimalarial drugs. A ball-and-stick model of artemisinin appears on the cover of this text.

  1. Locate the stereogenic centers in both drugs.
  2. Label each stereogenic center in mefloquine as R or S.
  3. What is the maximum number of stereoisomers possible for artemisinin?
  4. How are the N atoms in mefloquine hybridized?
  5. Can two molecules of artemisinin intermolecularly hydrogen bond to each other?
  6. What product is formed when mefloquine is treated with HCl?

How is each compound related to the simple sugar D-erythrose? Is it an enantiomer,diastereomer, or identical?

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