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

Pirlindole
Clinical data
Trade namesPirazidol
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability20–30%
Protein binding95%
Metabolismhepatic
Onset of action2 to 8 hours
Elimination half-lifeup to 8 days [1]
Excretionurine (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
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC15H18N2
Molar mass226.323 g·mol−1
3D model (JSmol)
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 pirindole (8).

See also

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-pyrazino[3,2,1-j,k]carbazoles". 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..
  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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