488. Amitriptylinoxide

Nomenclature

CAS number: 4317-14-0
3-(10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N,N-dimethyl-1-propanamine N-oxide; 10,11-dihydro-N,N-dimethyl-5H-dibenzo[a,d]cycloheptene-Δ5,γ-propylamine N-oxide; amitriptyline N-oxide; Ambivalon (Nattermann); Equilibrin (RPR).
C20H23NO; mol wt 293.40.
C 81.87%, H 7.90%, N 4.77%, O 5.45%.

Description and references

Centrally acting metabolite of amitriptyline, q.v. Prepn: J. B. Pedersen, GB 991651; idem, US 3299139 (1965, 1967 both to Dumex). Series of articles on pharmacology, pharmacokinetics, metabolism, clinical studies, toxicity studies, teratological studies: Arzneim.-Forsch. 28, 1873-1926 (1978). HPLC determn: K. M. Jensen, J. Chromatogr. 183, 321 (1980). Neuropharmacology: J. Hyttel et al., Acta Pharmacol. Toxicol. 47, 53 (1980). Toxicity study: H. Friehe, R. Fontaine, Arzneim.-Forsch. 28, 1898 (1978).

Chemical structure

Properties

Crystals, mp 228-230°. (Dihydrate, mp 102-103°.) LD50 in mice, guinea pigs, rabbits, dogs (mg/kg): between 330-460 orally; in mice, rats: 87, 25 i.v.; 320, 110 i.p. (Friehe, Fontaine).

Therapeutic Category

Antidepressant.

Keywords

Antidepressant; Tricyclics