13-06757. Noxiptilin [Archived]

Nomenclature

CAS number: 3362-45-6
10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-one O-[2-(dimethylamino)ethyl]oxime; 2-[[(10,11-dihydro-5H-dibenz[a,d]cyclohepten-5-ylidene)amino]oxy]-N,N-dimethylethylamine; 5-(2-dimethylaminoethyloximino)-5H-dibenzo[a,d]cyclohepta-1,4-diene; 5-[β-(dimethylamino)ethoxyimino]-10,11-dihydro-5H-dibenzo[a,d]cycloheptene; noxiptyline; dibenzoxin.
C19H22N2O; mol wt 294.39.
C 77.52%, H 7.53%, N 9.52%, O 5.43%.

Description and references

Prepn: Engelhard et al., DE 1198353 (1965); Schutz, Hoffmeister, DE 1225169; Schutz et al., US 3505321 (1966, 1970 both to Bayer); Wrigley, Leeming, GB 1045911 (1966 to Pfizer). Toxicity study: F. Hoffmeister et al., Arzneim.-Forsch. 19, 846 (1969). Series of articles on pharmacology, metabolism, clinical data: ibid. 458-467; 846-878.

Chemical structure

Properties

Free base, bp0.05 160-164°.

Derivative

Hydrochloride.

Nomenclature

CAS number: 4985-15-3
Bay 1521; Agedal (Bayer); Nogédal (Théraplix).
C19H22N2O.HCl; mol wt 330.85.
C 68.97%, H 7.01%, N 8.47%, O 4.84%, Cl 10.72%.

Properties

Crystals from ethanol + ethyl acetate, mp 185-187°. LD50 s.c. in mice: 240 mg/kg (Hoffmeister).

Therapeutic Category

Antidepressant.

Keywords

Antidepressant; Tricyclics

Status

This monograph has been retired and is no longer subject to revision or update.