The mechanism of action of doxepin is presumable linked to the effect on the adrenergic transmission in the CNS, in particular to the blockage of neuronal norepinephrine uptake. Doxepin is used in anxious-depressive and anxious conditions, neuroses, alcoholism, organic illnesses of the CNS, and psychoses. The most frequently used synonyms are adapin and sinequan.
7.1.2 Secondary amines—representatives of tricyclic antidepressants
Desipramine: Desipramine, 10,11-dihydro-5-[3-(methylamino)propyl]-5H-dibenz[b,f] azepine (7.1.13), differs from imipramine in that it contains only one methyl group on the nitrogen atom of the propylamine side chain. The suggested methods of desipramine synthesis are very simple, and the difference lies only in the manner in which the secondary methylamine group is introduced into the structure of the drug.
The first way of synthesis is by the alkylation of 10,11-dihydro-5H-dibenz[b,f]azepine using 1-bromo-3-chloropropane in the presence of sodium amide into a chloro derivative (7.1.12) and the subsequent reaction of this with methylamine, giving desipramine (7.1.13) [18-20].
NaNH2 /cSS\ CH3NH2
A second way is by alkylation of 10,11-dihydro-5H-dibenz[b,f]azepine with 3-(N-benzyl-N-methylamino)propyl chloride in the presence of sodium amide and the subsequent debenzylation of the resulting product (7.1.14) by hydrogenation using a palladium catalyst [21,22].
Was this article helpful?