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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
Excretion	urine (50–70%), feces (25–45%)
Identifiers
IUPAC name 8-methyl-2,3,3a,4,5,6-hexahydro-1H-pyrazinocarbazole
CAS Number	60762-57-4
PubChem CID	68802
IUPHAR/BPS	6638
DrugBank	DB09244
ChemSpider	62039
UNII	V39YPH45FZ
KEGG	D08392
ChEMBL	ChEMBL32350
CompTox Dashboard (EPA)	DTXSID8048230
Chemical and physical data
Formula	C15H18N2
Molar mass	226.323 g·mol
3D model (JSmol)	Interactive image
SMILES CC1=CC2=C(C=C1)N3CCNC4C3=C2CCC4

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. It is structurally and pharmacologically related to metralindole.

Synthesis

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 pirlindole (8).

See also

• Metralindole
• Tetrindole
• List of Russian drugs

References

1. Pöldinger W (1985). "Pirlindole: results of an open clinical study in out-patients and of a double-blind study against maprotiline.". Psychiatry the State of the Art. Boston, MA.: Springer. pp. 283–289. doi:10.1007/978-1-4613-2363-1_44. ISBN 978-1-4613-2363-1.
2. Bruhwyler J, Liégeois JF, Géczy J (July 1997). "Pirlindole: a selective reversible inhibitor of monoamine oxidase A. A review of its preclinical properties". Pharmacological Research. 36 (1): 23–33. doi:10.1006/phrs.1997.0196. PMID 9368911.
3. Filitis LN, Fedotova OA, Akalaeva TV, Bokanov AI, Ivanov PY, Neustroeva VD, Nyrkova VG, Pershin GN, Shvedov VI (1986). "Tetrahydrocarbazole derivatives and their antitubercular activity in vitro. I. N-Substituted hexahydro-1H-pyrazinocarbazoles". Khimiko-Farmatsevticheskii Zhurnal (in Russian). 20 (3): 300–303.
4. Ivanov PY, Alekseeva LM, Bokanov AI, Shvedov VI, Sheinker YN (January 1987). "New approach to the synthesis of pyrazidol". Pharmaceutical Chemistry Journal. 21 (1): 62–65. doi:10.1007/BF00764890. S2CID 22179419..
5. De Tullio P, Felikidis A, Pirotte B, Liégeois JF, Stachow M, Delarge J, Ceccato A, Hubert P, Crommen J, Géczy J (1998). "First Preparative Enantiomer Resolution of Pirlindole, a Potent Antidepressant Drug". Helvetica Chimica Acta. 81 (3–4): 539–547. doi:10.1002/hlca.19980810307. ISSN 0018-019X..
6. , FR 2132514  (1972 to Inst Im Sergo); CA, 78, 124628r
7. Massimo Ferrari, et al. EP 1044976  (2002 to Erregierre SpA).
8. Massimo Ferrari, et al. CZ20001348 (2000).
9. DE 2114230 
10. GB 1340529 
11. Chen Weidong, et al. CN 110950873  (2020 to Henan University).
12. Carla Patricia Da Costa Pereira Rosa, et al. WO 2018193415  (to Tecnimede Sociedade Tecnico Medicinal SA).
13. "N-(2-chloroethyl)-6-methyl-2,3,4,9-tetrahydrocarbazol-1-imine". PubMed. U.S. National Library of Medicine.

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