Dothiepin

Pale Yellow Low Melting Solid

Described in the 1960s by the Czech company Sdruzeni Podniku pro Zdravotnickon Vyrobu; SPOFA (Spofa, 1962)

A tricyclic antidepressant.

ChEBI: Dothiepin is a dibenzothiepine. It has a role as an antidepressant and an anticoronaviral agent.

Synthesis (Spofa, 1962): S-Benzylthiosalicylic acid is treated with polyphosphoric acid and the resulting cyclic ketone is reacted with 3-dimethylaminopropyl magnesium chloride to afford an alcohol which is dehydrated with sulfuric acid.

Synthesis of dosulepin

Dosulepin (also referred to as dothiepin) is a member of the TCA family and has similar clinical uses as amitrip- tyline, thus providing effective treatment of depression (Goldstein and Claghorn, 1980; Lancaster and Gonzales, 1989; Donovan et al., 1991) and also against pain (Feinmann et al., 1984; Caruso et al., 1987) and tinnitus. Like amitriptyline it has sedative properties, however its anti-muscarinic side-effects are less pronounced. Dosulepin is readily absorbed from the GI tract and extensively demethylated while undergoing a first-pass effect. Metabolic pathways include next to hydroxylation and N-oxidation steps, S-oxidation. Elimination half-lifes vary from 14 to 24 hours interindividually (Maguire et al., 1982; Yu et al., 1986; Ilett et al., 1993).