Pirlindole

From Wikipedia, the free encyclopedia
Jump to navigation Jump to search

Pirlindole
Clinical data
Trade namesLifril, Pirazidol
Routes of
administration		By mouth
ATC code
  • None
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability20–30%
Protein binding95%
Metabolismhepatic
Onset of action2–8 hours
Elimination half-lifeup to 8 days [1]
Excretionurine (50–70%), feces (25–45%)
Identifiers
  • 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
E number{{#property:P628}}
CompTox Dashboard (EPA)
  • {{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC15H18N2
Molar mass226.323 g·mol−1
3D model (JSmol)
  • 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.[2] It is structurally and pharmacologically related to metralindole.

Synthesis

[edit | edit source]
Error creating thumbnail:
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

[edit | edit source]

References

[edit | edit source]
  1. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  2. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  3. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  4. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value)..
  5. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value)..
  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. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
Stub icon

This drug article relating to the nervous system is a stub. You can help Wikipedia by expanding it.

Retrieved from "http://70.231.62.181/index.php?title=Pirlindole&oldid=10067182"