3429. Dothiepin

Nomenclature

CAS number: 113-53-1
3-Dibenzo[b,e]thiepin-11(6H)-ylidene-N,N-dimethyl-1-propanamine; N,N-dimethyldibenzo[b,e]thiepin-Δ11(6H),γ-propylamine; 11-(3-dimethylaminopropylidene)-6,11-dihydrodibenzo[b,e]thiepin; dosulepin.
C19H21NS; mol wt 295.44.
C 77.24%, H 7.16%, N 4.74%, S 10.85%.

Description and references

Tricyclic antidepressant. Prepn: M. Protiva et al., Experientia 18, 326 (1962); BE 618591; M. Protiva et al., US 3527766 (1962, 1970 both to SPOFA); M. Rajsner, M. Protiva, Cesk. Farm. 11, 404 (1962), C.A. 59, 2772g (1963). Synthesis of isomers: M. Rajsner et al., Collect. Czech. Chem. Commun. 34, 1963 (1969). Pharmacology: J. Metysova et al., Arzneim.-Forsch. 13, 1039 (1963). Clinical pharmacokinetics and metabolism: K. P. Maguire et al., Br. J. Clin. Pharmacol. 12, 405 (1981). HPLC determn in plasma: P. J. Taylor et al., J. Chromatogr. 581, 152 (1992). Review of clinical experience in depression: S. Donovan et al., Prog. Neuro-Psychopharmacol. Biol. Psychiatry 18, 1143-1162 (1994).

Chemical structure

Properties

bp0.05 171-172°. mp 55-57°.

Derivative

Hydrochloride.

Nomenclature

CAS number: 897-15-4
Prothiaden (Knoll).
C19H21NS.HCl; mol wt 331.90.
C 68.76%, H 6.68%, N 4.22%, S 9.66%, Cl 10.68%.

Properties

Crystals from ethanol-ether, mp 218-221°. uv max (methanol): 232, 260, 309 nm (log ε 4.41, 3.97, 3.53).

Therapeutic Category

Antidepressant.

Keywords

Antidepressant; Tricyclics