First-generation MAOIs like tranylcypromine (8), iproniazid (9), isocarboxazide (10), phenelzine (11), pheniprazine (12), and nialamide (13) revolutionized the treatment of depression.22 These are generally less utilized in current clinical practice due to their poor side-effect profile and potentially dangerous interactions with other drugs and foods, the latter reflecting the cheese, or tyramine, effect. The current leading MAOIs are tranylcypromine (8), phenelzine (11), and moclobemide (14).
The first generations of MAOI antidepressants were hydrazine derivatives, e.g., phenelzine and isocarboxazide, which are probably converted into hydrazine to produce long-lasting inhibition of MAO. Tranylcypromine is essentially a cyclized amphetamine without the covalent bond. Selegiline (15), a propargylamine MAOI, contains a reactive acetylenic bond that interacts irreversibly with the flavin cofactor of MAO resulting in prolonged MAOI activity. Selegiline is still used in clinical practice today, mainly in Parkinson's disease. However, a new patch delivery formulation of selegiline that is proposed to overcome the adverse events associated with MAOIs is in Phase III studies for major depression. Rasagiline (16) is currently marketed for Parkinson's disease in Europe.
The major challenge over the last 60 years has been to synthesize short-acting, reversible MAOIs, of which moclobemide (14), rasagiline (16), toloxatone (17), befloxatone (18), brofaromine (19), secloramine (20), and cimoxatone (21) are representatives of third-generation MAOIs.
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