Pirlindole (Lifril, Pyrazidol) is mainly a

reversible inhibitor of monoamine oxidase A Monoamine oxidase inhibitors (MAOIs) are a class of drugs that inhibit the activity of one or both monoamine oxidase enzymes: monoamine oxidase A (MAO-A) and monoamine oxidase B (MAO-B). They are best known as effective antidepressants, espe ...

(RIMA) and secondly a SNRI which was developed and is used in

Russia Russia (, , ), or the Russian Federation, is a transcontinental country spanning Eastern Europe and Northern Asia. It is the largest country in the world, with its internationally recognised territory covering , and encompassing one-eig ...

as an antidepressant. It is

structurally A structure is an arrangement and organization of interrelated elements in a material object or system, or the object or system so organized. Material structures include man-made objects such as buildings and machines and natural objects such as ...

and pharmacologically related to

metralindole Metralindole (Inkazan) is a reversible inhibitor of monoamine oxidase A (RIMA) which was investigated in Russia as a potential antidepressant. It is structurally A structure is an arrangement and organization of interrelated elements in a mat ...

Synthesis

The

Fischer indole synthesis The Fischer indole synthesis is a chemical reaction that produces the aromatic heterocycle indole from a (substituted) phenylhydrazine and an aldehyde or ketone under acidic conditions. The reaction was discovered in 1883 by Emil Fischer. Today ...

between ''p''-Tolylhydrazine Hydrochloride 37-60-5(1) and

1,2-Cyclohexanedione 1,2-Cyclohexanedione is an organic compound with the formula (CH)(CO). It is one of three isomeric cyclohexanediones. It is a colorless compound that is soluble in a variety of organic solvents. It can be prepared by oxidation of cyclohexanon ...

65-87-7(2) gives 6-methyl-2,3,4,9-tetrahydrocarbazol-1-one 449-48-7(3). Imine formation with

ethanolamine Ethanolamine (2-aminoethanol, monoethanolamine, ETA, or MEA) is an organic chemical compound with the formula or . The molecule is bifunctional, containing both a primary amine and a primary alcohol. Ethanolamine is a colorless, viscous liquid w ...

41-43-5(4) give
CID:2838578
(5). Halogenation with

phosphorus oxychloride Phosphoryl chloride (commonly called phosphorus oxychloride) is a colourless liquid with the formula . It hydrolyses in moist air releasing phosphoric acid and fumes of hydrogen chloride. It is manufactured industrially on a large scale from pho ...

gives (6). Intramolcular alkylation with the indole nitrogen resulted in Dehydropirlindole 5804-32-9(7). Reduction of the imine with

sodium borohydride Sodium borohydride, also known as sodium tetrahydridoborate and sodium tetrahydroborate, is an inorganic compound with the formula Na BH4. This white solid, usually encountered as an aqueous basic solution, is a reducing agent that finds applica ...

completes the synthesis of ' (8).

References

Reversible inhibitors of MAO-A Antidepressants Monoamine oxidase inhibitors Carbazoles Russian drugs {{nervous-system-drug-stub

Synthesis

See also

References