Pirlindole

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.^[2] It is structurally and pharmacologically related to metralindole.

Pirlindole

Clinical data
Trade names	Lifril, Pirazidol
Routes of administration	By mouth
ATC code	None
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	20–30%
Protein binding	95%
Metabolism	hepatic
Onset of action	2–8 hours
Elimination half-life	up to 8 days [1]
Excretion	urine (50–70%), feces (25–45%)
Identifiers
IUPAC name 8-methyl-2,3,3a,4,5,6-hexahydro-1H-pyrazino[3,2,1-jk]carbazole
CAS Number	60762-57-4
PubChem CID	68802
IUPHAR/BPS	6638
DrugBank	DB09244 Y
ChemSpider	62039
UNII	V39YPH45FZ
KEGG	D08392
ChEMBL	ChEMBL32350
CompTox Dashboard (EPA)	DTXSID8048230
Chemical and physical data
Formula	C15H18N2
Molar mass	226.323 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC1=CC2=C(C=C1)N3CCNC4C3=C2CCC4

Synthesis

Synthesis:^[3][4][5] Patents:^{[6][7][8][9][10]} Sino:^[11] Enantiomers:^[12]

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).^[13] 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

• Metralindole
• Tetrindole
• List of Russian drugs