Spiroxatrine

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	1054-88-2 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL300555 ;
ChemSpider	5078 ;
IUPHAR/BPS	53;
MeSH	Spiroxatrine
PubChem CID	5268;
UNII	DR0QR50ALL ;
CompTox Dashboard (EPA)	DTXSID3045198 ;
	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) Key: JVGBTTIJPBFLTE-UHFFFAOYSA-N ;
	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). verify (what is ?) Infobox references

Spiroxatrine is a drug which acts as a selective antagonist at both the 5-HT_1A receptor and the α_2C adrenergic receptor.^[1] It is an analog of spiperone and also has some dopamine antagonist effects.

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.

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

^ 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.
^ Janssen Paul Adriaan Jan, U.S. patent 3,238,216 (1966 to Res Lab Dr C Janssen N V).

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[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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