Dothiepin Property

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

RIDADR 

3249

HazardClass 

6.1(b)

PackingGroup 

III

Hazardous Substances Data

113-53-1(Hazardous Substances Data)

Toxicity

LD50 oral in rat: 450mg/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H361Suspected of damaging fertility or the unborn child

H362May cause harm to breast-fed children

Precautionary statements

P201Obtain special instructions before use.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P263Avoid contact during pregnancy/while nursing.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P308+P313IF exposed or concerned: Get medical advice/attention.

Dothiepin Chemical Properties,Usage,Production

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).