Pirlindole

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Pirlindole, sold under the brand names Lifril and Pyrazidol, is mainly a reversible inhibitor of monoamine oxidase A (RIMA) and secondly a serotonin–norepinephrine reuptake inhibitor (SNRI) which was developed and is used in Russia as an antidepressant.[1] It is structurally and pharmacologically related to metralindole.

Synthesis

File:Pirlindole synthesis.svg
Synthesis:[2][3][4] Patents:[5][6][7][8][9] Sino:[10] Enantiomers:[11]

The Fischer indole synthesis between p-Tolylhydrazine Hydrochloride [637-60-5] (1) and 1,2-Cyclohexanedione [765-87-7] (2) gives 6-methyl-2,3,4,9-tetrahydrocarbazol-1-one [3449-48-7] (3). Imine formation with ethanolamine [141-43-5] (4) gives CID:2838578 (5). Halogenation with phosphorus oxychloride gives (6).[12] Intramolcular alkylation with the indole nitrogen resulted in Dehydropirlindole [75804-32-9] (7). Reduction of the imine with sodium borohydride completes the synthesis of pirlindole (8).

See also

References

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  5. ↑ , <templatestyles src="Citation/styles.css"/>Template:Citation/make link Script error: No such module "Check for unknown parameters". (1972 to Inst Im Sergo); CA, 78, 124628r
  6. ↑ Massimo Ferrari, et al. <templatestyles src="Citation/styles.css"/>Template:Citation/make link Script error: No such module "Check for unknown parameters". (2002 to Erregierre SpA).
  7. ↑ Massimo Ferrari, et al. CZ20001348 (2000).
  8. ↑ <templatestyles src="Citation/styles.css"/>Template:Citation/make link Script error: No such module "Check for unknown parameters".
  9. ↑ <templatestyles src="Citation/styles.css"/>Template:Citation/make link Script error: No such module "Check for unknown parameters".
  10. ↑ Chen Weidong, et al. <templatestyles src="Citation/styles.css"/>Template:Citation/make link Script error: No such module "Check for unknown parameters". (2020 to Henan University).
  11. ↑ Carla Patricia Da Costa Pereira Rosa, et al. <templatestyles src="Citation/styles.css"/>Template:Citation/make link Script error: No such module "Check for unknown parameters". (to Tecnimede Sociedade Tecnico Medicinal SA).
  12. ↑ Script error: No such module "citation/CS1".

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