5748. Maprotiline

Nomenclature

CAS number: 10262-69-8
N-Methyl-9,10-ethanoanthracene-9(10H)-propanamine; 9-(γ-methylaminopropyl)-9,10-dihydro-9,10-ethanoanthracene; 1-(3-methylaminopropyl)dibenzo[b,e]bicyclo[2.2.2]octadiene.
C20H23N; mol wt 277.40.
C 86.59%, H 8.36%, N 5.05%.

Description and references

Prepn: P. Schmidt et al., US 3399201 (1968 to Ciba). Synthesis, NMR, mass spectra: M. Wilhelm, P. Schmidt, Helv. Chim. Acta 52, 1385 (1969). Toxicity: R. Hess et al., Boll. Chim. Farm. 112, 782 (1973), C.A. 81, 33479p (1974). Review of pharmacology and therapeutic efficacy: R. M. Pinder et al., Drugs 13, 321 (1977). Comprehensive description: S. K. Suh, J. B. Smith, Anal. Profiles Drug Subs. 15, 393-426 (1986).

Chemical structure

Properties

mp 92-94°.

Derivative

Hydrochloride.

Nomenclature

CAS number: 10347-81-6
Ba-34276; Deprilept (Promonta); Ludiomil (Novartis); Psymion (TAD).
C20H23N.HCl; mol wt 313.86.
C 76.54%, H 7.71%, N 4.46%, Cl 11.30%.

Properties

Crystals from isopropanol, mp 230-232°. Freely sol in methanol and chloroform, slightly sol in water. Practically insol in isooctane. LD50 in mice, rats (mg/kg): ≈750, ≈900 orally (Hess).

Therapeutic Category

Antidepressant.

Keywords

Antidepressant; Tetracyclics