Structureactivity Relations

Tricyclic and tetracyclic compounds are categorized on the basis of their chemical structure (Figure 12-1). The tricyclics have a central three-ring structure, hence the name. The tertiary-amine tricyclics, such as amitriptyline and imipramine, have two methyl groups at the end of the side chain. These compounds can be demethylated to secondary amines, such as desipramine and nortriptyline. The tetracyclic compound maprotiline (Ludiomil) has a four-ring central structure. Five tertiary amines have been marketed in the United States—amitriptyline (Elavil), clomipramine (Anafranil), doxepin (Sinequan), imipramine (Tofranil), and trimipramine (Surmontil). The three secondary-amine compounds are desipramine (Norpramin, Pertofrane), nortriptyline (Aventyl, Pamelor), and protriptyline (Vivactil). All of these compounds, in addition to amoxapine (Asendin) and maprotiline (Ludiomil), have been approved for use in major depression with the exception of clomipramine (Anafranil), which in the United States is approved for use only in obsessive-compulsive disorder (OCD).

FIGURE 12-1. Drugs marketed in the United States as tricyclics (1-9) and a tetracyclic (10).

1. Imipramine ego ch3

ch2ch2ch2-n ch3

3. Amitriptyline oco ÇH3


5. Clomipramine oça CI ch3

ch2ch2CH2-N ch3

7. Doxepin oCo CH3

h V"3

chch2ch2-n ch3

9. Amoxapine H

9 cCcf

2. Desipramine

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