Spiroxatrine

Spiroxatrine is a drug which acts as a selective antagonist at both the 5-HT1A receptor and the α2C adrenergic receptor.[1] It is an analog of spiperone and also has some dopamine antagonist effects.

Spiroxatrine
Names
IUPAC name
8-(2,3-Dihydro-1,4-benzodioxin-2-ylmethyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
MeSH Spiroxatrine
PubChem CID
UNII
InChI
  • InChI=1S/C22H25N3O3/c26-21-22(25(16-23-21)17-6-2-1-3-7-17)10-12-24(13-11-22)14-18-15-27-19-8-4-5-9-20(19)28-18/h1-9,18H,10-16H2,(H,23,26) Y
    Key: JVGBTTIJPBFLTE-UHFFFAOYSA-N Y
SMILES
  • O=C2NCN(c1ccccc1)C23CCN(CC3)CC4Oc5ccccc5OC4
Properties
Chemical formula
 C22H25N3O3
Molar mass 379.460 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Synthesis

Note well that the piperidine intermediate has a venerable history & has been incorporated into in the synthesis of the following drugs: Spiperone, Fluspirilene, Ro65-6570, RP-23618, Spirilene, Spiramide, R 5260 [1109-69-9], PCP-Antipsychotic mixture. Although it looks like most agents are antipsychotics, more applications might be possible. Indeed, manipulations to the molecular structure meant some of the agents behave as opioids.

Patent (Ex VII):[2]

Convergent synthesis between 2-Bromomethyl-1,4-benzodioxane [2164-34-3] (1) and 1-Phenyl-1,3,8-triazaspiro[4.5]decan-4-one [1021-25-6] (2) completes the synthesis of Spiroxatrine (3)

References
  1. Terrón, J. A.; Ibarra, M; Ransanz, V; Hong, E; Villalón, C. M. (1993). "The alpha-antiadrenergic properties of spiroxatrine, a ligand of serotonergic 5-HT1A receptors". Archivos del Instituto de Cardiología de México. 63 (4): 289–95. PMID 8105762.
  2. Janssen Paul Adriaan Jan, U.S. Patent 3,238,216 (1966 to Res Lab Dr C Janssen N V).


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