Ipsapirone

Ipsapirone is a selective 5-HT1A receptor partial agonist of the piperazine and azapirone chemical classes.[1] It has antidepressant and anxiolytic effects.[1] Ipsapirone was studied in several placebo-controlled trials for depression and continues to be used in research.[2]

Ipsapirone
Clinical data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: uncontrolled
Pharmacokinetic data
Elimination half-life1.3-2.7 hours
Identifiers
IUPAC name
  • 9,9-dioxo-8-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]-
    9λ6-thia-8-azabicyclo[4.3.0]nona-1,3,5-trien-7-one
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H23N5O3S
Molar mass401.49 g·mol−1
3D model (JSmol)
SMILES
  • O=C2c1ccccc1S(=O)(=O)N2CCCCN4CCN(c3ncccn3)CC4
InChI
  • InChI=1S/C19H23N5O3S/c25-18-16-6-1-2-7-17(16)28(26,27)24(18)11-4-3-10-22-12-14-23(15-13-22)19-20-8-5-9-21-19/h1-2,5-9H,3-4,10-15H2 Y
  • Key:TZJUVVIWVWFLCD-UHFFFAOYSA-N Y
  (verify)

Patented Uses

Synthesis

Note that this is a homologue of Revospirone differing only in respect of the length of the sidehain.

Synthesis:[6] Patent (Ex 7):[7]

The alkylation of Saccharin [81-07-2] (1) with tetramethylenedibromide [110-52-1] (2) gives N-bromobutylsaccharin [103564-59-6] (3). Alkylation of this with 2-(1-Piperazinyl)pyrimidine [20980-22-7] (4) yields Ipsapirone (5).

See also

References
  1. Fanelli RJ, Schuurman T, Glaser T, Traber J (1990). "Ipsapirone: a novel anxiolytic and selective 5-HT1A receptor ligand". Progress in Clinical and Biological Research. 361: 461–7. PMID 1981264.
  2. Chessick, Cheryl A.; Allen, Michael H.; Thase, Michael E.; Batista Miralha Da Cunha, Angelo ABC; Kapczinski, Flávio; Silva De Lima, Mauricio; Dos Santos Souza, Juliano JSS (Jul 19, 2006). "Azapirones for generalized anxiety disorder". Cochrane Database Syst Rev (3): CD006115. doi:10.1002/14651858.CD006115. PMID 16856115.
  3. Jonathan Turner & Belinda Cole, WO 1993004681 (to Bayer AG).
  4. Jorg Traber & Klaus Opitz, U.S. Patent 4,895,848 (to IROPONWERKE & Co KG A CORP OF GERMANY GmbH, Bayer AG).
  5. Klaus Opitz, Maria-Luise Weischer & Jorg Traber, U.S. Patent 4,871,738 (1989 to Bayer AG).
  6. Castaer, J .; Prous, J .; Ipsapirone. Drugs Fut 1986, 11, 7, 565.
  7. Wolfgang Dr Dompert, 5 More », DE 3321969 (1984 to Troponwerke Gmbh & Co Kg).



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