Dothiepin Chemical Properties

Melting point:

55-57°

Boiling point:

bp0.05 171-172°

Density 

1.1022 (rough estimate)

refractive index 

1.5300 (estimate)

storage temp. 

Refrigerator

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Thick Oil to Low-Melting Solid

pka

9.35±0.28(Predicted)

color 

Off-White to Light Yellow

Safety Information

RIDADR 

3249

HazardClass 

6.1(b)

PackingGroup 

III

Hazardous Substances Data

113-53-1(Hazardous Substances Data)

Toxicity

LD50 oral in rat: 450mg/kg

Dothiepin Usage And Synthesis

Chemical Properties

Pale Yellow Low Melting Solid

History

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

Uses

A tricyclic antidepressant.

Definition

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

Synthesis Reference(s)

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

Clinical Use

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).

Dothiepin(113-53-1)Related Product Information

• Citalopram
• Trazodone
• CIS,TRANS-DOTHIEPIN-D3,100/MLINMETHANOL
• dothiepin sulfoxide,Dothiepin S-oxide
• DOTHIEPIN HYDROCHLORIDE,DOTHIEPIN HCL,Dothiepin·hydrochloric acid,DOSULEPIN HYDROCHLORIDE (DOTHIEPIN HYDROCHLORIDE)
• DOSULEPIN (DOTHIEPIN) HYDROCHLORIDE
• DOTHIEPIN-D3
• 11-(1-Methyl-4-piperidylidene)-6,11-dihydrodibenzo(b,e)thiepine-9-carb oxylic acid HCl
• (E)-9-Fluoro-11-(3-dimethylaminopropylidene)-6,11-dihydrodibenzo(b,e)t hiepin hydrogen maleate
• Dothiepin
• 3-dibenzo[b,e]thiepin-11(6H)-ylidene-8-methyl-8-azabicyclo[3.2.1]octane hydrochloride
• Tropatepine