4100. Flesinoxan

Nomenclature

CAS number: 98206-10-1
N-[2-[4-[(2R)-2,3-Dihydro-2-(hydroxymethyl)-1,4-benzodioxin-5-yl]-1-piperazinyl]ethyl]-4-fluorobenzamide; (+)-(S)-p-fluoro-N-[2-[4-[2-(hydroxymethyl)-1,4-benzodioxan-5-yl]-1-piperazinyl]ethyl]benzamide.
C22H26FN3O4; mol wt 415.46.
C 63.60%, H 6.31%, F 4.57%, N 10.11%, O 15.40%.

Description and references

Serotonin (5-HT1A)-receptor agonist; phenylpiperazine derivative. Prepn: J. Hartog et al., EP 138280; eidem, US 4833142 (1985, 1989 both to Duphar). Synthesis and resolution of enantiomers: M. D. Ennis, N. B. Ghazal, Tetrahedron Lett. 33, 6287 (1992). GC determn in plasma and urine: M. P. van Berkel et al., Methodol. Surv. Biochem. Anal. 18, 209 (1988). Pharmacology: J. Schipper et al., Hum. Psychopharmacol. 6, S53 (1991). Clinical evaluation in depression: P. Grof et al., Int. Clin. Psychopharmacol. 8, 167 (1993).

Chemical structure

Properties

[α]D +26° (c = 1 in methanol).

Derivative

Hydrochloride.

Nomenclature

CAS number: 98205-89-1
DU-29373.
C22H26FN3O4.HCl; mol wt 451.92.
C 58.47%, H 6.02%, F 4.20%, N 9.30%, O 14.16%, Cl 7.84%.

Properties

mp 184.5-185.5°. Also reported as crystals from ethanol/ether, mp 183.0-184.0° (Ennis). [α]D +25° (c = 1 in methanol). Freely sol in water; sparingly sol in ethanol.

Therapeutic Category

Anxiolytic.

Keywords

Anxiolytic; Arylpiperazines; Serotonin Receptor Agonist