ChemicalBook--->CAS DataBase List--->113-53-1

113-53-1

113-53-1 Structure

113-53-1 Structure
IdentificationBack Directory
[Name]

Dothiepin
[CAS]

113-53-1
[Synonyms]

iz914
Dothep
IZ 914
dosulepin
Methiaden
DOTHIEPIN
Prothiaden
Dosulepine
Prothiadene
Dolsulepine
Prothiaden spofa
Dothiepin-d3 Maleate
Dothiepin (cis/trans)
CIS,TRANS-DOTHIEPIN,1.0MG/MLINMETHANOL
Dibenzo[b,e]thiepin, 1-propanamine deriv.
3-Dibenzo[b,e]thiepin-11(6H)-ylidene-N,N-diMethyl-
N,N-Dimethyl- dibenzo[b,e]thiepin-11(6H),-propylamine
3-Dibenzo[b,e]thiepin-11(6H)-ylidine-N,N-dimethyl-propanamine
3-Dibenzo(b,e)thiepin-11(6H)-ylidene-N,N-dimethyl-1-propamine
3-dibenzo(b,e)thiepin-11(6h)-ylidene-n,n-dimethyl-1-propanamin
11-(3-Dimethylaminopropylidene)-6,11-dihydrodibenzo(b,e)thiepin
3-Dibenzo[b,e]thiepin-11(6H)-ylidene-N,N-dimethyl-1-propanamine
3-DIBENZO[B,E] THIEPIN-11-(6H)-YLIDENE-N,N-DIMETHYL-PROPONAMINE
Dibenzo[b,e]thiepin-delta11(6H),gamma-propylamine, N,N-dimethyl-
1-Propanamine, 3-dibenzo[b,e]thiepin-11(6H)-ylidene-N,N-dimethyl-
3-(6,11-dihydrodibenzo(b,e)thiepin-11-ylidene)propyldimethylamine
N,N-Dimethyldibenzo(b,e)thiepin-delta-sup(11(6H),gamma)propylamine
(3E)-3-Dibenzo[b,E]thiepin-11(6H)-ylidene-N,N-dimethyl-1-propanamine
(E)-3-[Dibenzo[b,e]thiepin-11(6H)-ylidene]-N,N-dimethyl-1-propanamine
(E)-3-[Dibenzo[b,e]thiepin-11(6H)-ylidene]-N,N-dimethylpropane-1-amine
n,n-dimethyl-3-(dibenzo(b,e)thiepin-delta-sup(11(6h),gamma))-propylamin
DOTHIEPIN,3-DIBENZO[B,E] THIEPIN-11-(6H)-YLIDENE-N,N-DIMETHYL-PROPONAMINE
Propylamine, N,N-dimethyl-3-(dibenzo(b,e)thiepin-delta-sup(11(6H),gamma))-
[EINECS(EC#)]

204-031-2
[Molecular Formula]

C19H21NS
[MDL Number]

MFCD00242922
[MOL File]

113-53-1.mol
[Molecular Weight]

295.44
Chemical PropertiesBack Directory
[Melting point ]

55-57°
[Boiling point ]

bp0.05 171-172°
[density ]

1.1022 (rough estimate)
[refractive index ]

1.5300 (estimate)
[storage temp. ]

Refrigerator
[pka]

9.35±0.28(Predicted)
Safety DataBack Directory
[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 InformationBack Directory
[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
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).
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