pirlindole pirlindole pirlindole (lifril, pyrazidol) is mainly a reversible inhibitor of monoamine oxidase a (rima) and secondly a snri which was developed and is used in russia as an antidepressant. it is structurally and pharmacologically related to metralindole. pirlindoleclinical datatrade namespirazidolroutes ofadministrationoralatc codenonelegal statuslegal status in general: ℞ (prescription only) pharmacokinetic databioavailability20–30%protein binding95%metabolismhepaticonset of action2 to 8 hourselimination half-lifeup to 8 days excretionurine (50–70%), feces (25–45%)identifiers iupac name 8-methyl-2,3,3a,4,5,6-hexahydro-1h-pyrazinocarbazole cas number60762-57-4pubchem cid68802iuphar/bps6638drugbankdb09244 ychemspider62039uniiv39yph45fzkeggd08392chemblchembl32350comptox dashboard (epa)dtxsid8048230 chemical and physical dataformulac15h18n2molar mass226.323 g·mol−13d model (jsmol)interactive image smiles cc1=cc2=c(c=c1)n3ccnc4c3=c2ccc4 synthesis synthesis: patents: sino: enantiomers: the fischer indole synthesis between p-tolylhydrazine hydrochloride (1) and 1,2-cyclohexanedione (2) gives 6-methyl-2,3,4,9-tetrahydrocarbazol-1-one (3). imine formation with ethanolamine (4) gives cid:2838578 (5). halogenation with phosphorus oxychloride gives (6). intramolcular alkylation with the indole nitrogen resulted in dehydropirlindole (7). reduction of the imine with sodium borohydride completes the synthesis of pirindole (8).