6153. Metralindole

Nomenclature

CAS number: 54188-38-4
2,4,5,6-Tetrahydro-9-methoxy-4-methyl-1H-3,4,6a-triazafluoranthene; 3-methyl-8-methoxy-3H-1,2,5,6-tetrahydropyrazino[1,2,3-ab]-β-carboline.
C15H17N3O; mol wt 255.31.
C 70.57%, H 6.71%, N 16.46%, O 6.27%.

Description and references

Heterocyclic β-carboline derivative used as an antidepressant. Prepn: R. G. Glushkov et al., DE 2357320; eidem, US 4088647 (1974, 1978 both to All Union Khim.-Farm Instit. USSR); eidem, Khim. Farm. Zh. 16, 1054 (1982), C.A. 98, 53831b (1983). Psychotropic activity, toxicity: M. D. Mashkovsky et al., DE 2356091; eidem, US 3959470 (1974, 1976 both to All Union Khim.-Farm. Instit. USSR). Pharmacology: N. I. Andreeva, M. D. Mashkovsky, Farmakol. Toksikol. (Moscow) 43, 133 (1980). Effect on the EEG of the brain cortex: L. F. Roshchina, ibid. 349. Effect on adrenergic neurotransmission: L. V. Panasiuk et al., ibid. 45, 13 (1982). Clinical studies: M. D. Mashkovsky, N. I. Andreeva, Zh. Nevropatol. Psikhiatr. 84, 410 (1984).

Chemical structure

Properties

Crystals, mp 164-165°.

Derivative

Hydrochloride.

Nomenclature

CAS number: 53734-79-5
Incazan (USSR).
C15H17N3O.HCl; mol wt 291.78.
C 61.75%, H 6.22%, N 14.40%, O 5.48%, Cl 12.15%.

Properties

Off-white odorless powder with bitter taste. mp 305-308°. Sol in water. LD50 orally in mice: 445 mg/kg (Mashkovsky, 1976).

Therapeutic Category

Antidepressant.

Keywords

Antidepressant; Tetracyclics