Pirlindole

Pirlindole
Clinical data
Trade names	Pirazidol
Routes of; administration	Oral
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 to 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-pyrazino[3,2,1-jk]carbazole;
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−1
3D model (JSmol)	Interactive image;
	SMILES CC1=CC2=C(C=C1)N3CCNC4C3=C2CCC4;

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.

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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).

[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. 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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[1] [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] [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] [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] [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] [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] [6]
, FR 2132514 (1972 to Inst Im Sergo); CA, 78, 124628r

[7] [7]
Massimo Ferrari, et al. EP 1044976 (2002 to Erregierre SpA).

[8] [8]
Massimo Ferrari, et al. CZ20001348 (2000).

[9] [9]
DE 2114230

[10] [10]
GB 1340529

[11] [11]
Chen Weidong, et al. CN 110950873 (2020 to Henan University).

[12] [12]
Carla Patricia Da Costa Pereira Rosa, et al. WO 2018193415 (to Tecnimede Sociedade Tecnico Medicinal SA).

[13] [13]
"N-(2-chloroethyl)-6-methyl-2,3,4,9-tetrahydrocarbazol-1-imine". PubMed. U.S. National Library of Medicine.

[2]

[1]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]

[12]

[13]

Pirlindole

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Synthesis

See also

References

Clinical data

Trade names	Pirazidol
Routes of administration	Oral
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 to 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