Revospirone

Revospirone (Bay Vq 7813) is an azapirone drug which was patented as a veterinary tranquilizer but was never marketed.[1] It acts as a selective 5-HT1A receptor partial agonist.[2] Similarly to other azapirones such as buspirone, revospirone produces 1-(2-pyrimidinyl)piperazine (1-PP) as an active metabolite.[2] As a result, it also acts as an α2-adrenergic receptor antagonist to an extent.[2]

Revospirone
Clinical data
ATC code
  • none
Identifiers
IUPAC name
  • 1,1-dioxo-2-[3-(4-pyrimidin-2-ylpiperazin-1-yl)propyl]-1,2-benzothiazol-3-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H21N5O3S
Molar mass387.46 g·mol−1

Synthesis
Patents:[3][4]

The alkylation of Saccharin (1) with 1-Bromo-3-chloropropane (2) would give 2-(3-chloropropyl)-1,1-dioxo-1,2-benzothiazol-3-one [544695-21-8] (3). Alkylation with 2-(1-Piperazinyl)pyrimidine [20980-22-7] (4) then completes the synthesis of Revospirone (5).

Alternately, if 1,3-Dibromopropane was used get CID:287571.

References
  1. Macdonald F (1997). Dictionary of Pharmacological Agents. CRC Press. p. 1744. ISBN 978-0-412-46630-4. Retrieved 13 May 2012.
  2. Löscher W, Witte U, Fredow G, Traber J, Glaser T (September 1990). "The behavioural responses to 8-OH-DPAT, ipsapirone and the novel 5-HT1A receptor agonist Bay Vq 7813 in the pig". Naunyn-Schmiedeberg's Archives of Pharmacology. 342 (3): 271–7. doi:10.1007/bf00169437. PMID 2149168. S2CID 24769939.
  3. Wolfgang Dr Dompert, 5 More », DE 3321969 (1984 to Troponwerke Gmbh & Co Kg).
  4. Peter-Rudolf Seidel, U.S. Patent 5,187,276 (1993 to Bayer AG).


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