4938. Indeloxazine Hydrochloride

Nomenclature

CAS number: 65043-22-3
2-[(1H-Inden-7-yloxy)methyl]morpholine hydrochloride; (±)-2-[(7-indenyloxy)methyl]morpholine hydrochloride; YM-08054-1; Elen (Yamanouchi); Noin (Schering).
C14H18ClNO2; mol wt 267.75.
C 62.80%, H 6.78%, Cl 13.24%, N 5.23%, O 11.95%.

Description and references

Serotonin uptake inhibitor. Prepn: M. Masuo et al., DE 2601703; eidem, US 4109088 (1976, 1978 both to Yamanouchi). Synthesis and resolution of isomers: T. Kojima et al., Chem. Pharm. Bull. 33, 3766 (1985). Pharmacology and toxicity: S. Tachikawa et al., Arch. Int. Pharmacodyn. 238, 81 (1979). Inhibition of synaptosomal uptake of serotonin and noradrenaline: M. Harada, H. Maeno, Biochem. Pharmacol. 28, 2645 (1979). GLC determn in human plasma: A. G. Hayes, T. Chang, J. Chromatogr. 272, 176 (1983).

Chemical structure

Properties

Polymorphic; pale yellow needles from methanol, mp 169-170°; colorless, acicular crystals from acetone, mp 155-156°. LD50 in mice (mg/kg): 47 i.v. (Tachikawa).

Derivative

(+)-Form.

Properties

Crystals from ethanol, mp 112-113°. [α]D21 +4.9° (c = 5 in methanol).

Derivative

()-Form.

Properties

Crystals from isopropanol, mp 142-142.5°. [α]D20 4.9° (c = 5 in methanol).

Therapeutic Category

Antidepressant; nootropic.

Keywords

Antidepressant; Bicyclics; Nootropic; Serotonin Uptake Inhibitor