113-53-1

Basic information

• Product Name: DOTHIEPIN
• Synonyms: (3E)-3-Dibenzo[b,E]thiepin-11(6H)-ylidene-N,N-dimethyl-1-propanamine;11-(3-Dimethylaminopropylidene)-6,11-dihydrodibenzo(b,e)thiepin;1-Propanamine, 3-dibenzo[b,e]thiepin-11(6H)-ylidene-N,N-dimethyl-;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;3-Dibenzo[b,e]thiepin-11(6H)-ylidine-N,N-dimethyl-propanamine;Dibenzo[b,e]thiepin, 1-propanamine deriv.;Dibenzo[b,e]thiepin-delta11(6H),gamma-propylamine, N,N-dimethyl-
• CAS NO: 113-53-1
• Molecular Formula: C₁₉H₂₁NS
• Molecular Weight: 295.44
• EINECS: 204-031-2
• Product Categories: Chemical Amines;Amines;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 113-53-1.mol
• Article Data: 1

Chemical Properties

• Melting Point: 55-57°
• Boiling Point: bp0.05 171-172°
• Flash Point: 214.398 °C
• Appearance: Pale yellow low melting solid
• Density: 1.1022 (rough estimate)
• Refractive Index: 1.5300 (estimate)
• Storage Temp.: Refrigerator
• PKA: 9.35±0.28(Predicted)
• CAS DataBase Reference: DOTHIEPIN(CAS DataBase Reference)
• NIST Chemistry Reference: DOTHIEPIN(113-53-1)
• EPA Substance Registry System: DOTHIEPIN(113-53-1)

Safety Data

• RIDADR: 3249
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 113-53-1(Hazardous Substances Data)

Usage

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.

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).

InChI:InChI=1/C19H21NS/c1-20(2)13-7-11-17-16-9-4-3-8-15(16)14-21-19-12-6-5-10-18(17)19/h3-6,8-12H,7,13-14H2,1-2H3/b17-11-

Upstream product

• 1531-85-7 11-oxo-11-(dimethylaminopropyl)-6,11-dihydrodibenz-(b,e)thiepin 

Downstream Products

• 897-15-4 dothiepin hydrochloride 

Related news

Short communicationEffects of DOTHIEPIN (cas 113-53-1) on nociceptive flexion reflex and diffuse noxious inhibitory controls in humans08/28/2019

The analgesic activity of dothiepin (an antidepressant interacting with serotonin receptors) was studied (double-blind) in humans. A significant increase in nociceptive flexion reflex threshold and subjective pain threshold was observed after a 14-day dothiepin treatment. The effects of dothiepi...detailed

ORIGINAL ARTICLEUse of alizarin red S as a chromogenic agent for the colorimetric determination of DOTHIEPIN (cas 113-53-1) hydrochloride in pharmaceutical formulations08/27/2019

The present study describes two simple, rapid, selective and cost-effective spectrophotometric methods for the determination of dothiepin hydrochloride (DOTH), an antidepressant drug, in bulk drug and pharmaceutical formulations. The first method (method A) is based on the formation of yellow co...detailed

Pharmacology letter Accelerated communicationEffect of DOTHIEPIN (cas 113-53-1) on gastric ulceration mediated by lipid derived eicosanoids08/26/2019

Dothiepin, a tricyclic antidepressant, significantly inhibited the development of gastric ulcers induced by alcohol, aspirin, indomethacin and Shay's pyloric ligation. Antisecretory studies in pyloric ligated rats revealed that the drug at a dose of 100 mg/kg significantly reduced total aci...detailed

A fatal DOTHIEPIN (cas 113-53-1) overdose08/25/2019

High pressure liquid chromatography coupled to photodiode array detector and capillary gas chromatography coupled to mass spectrometry were employed to quantify dothiepin in biological fluids, tissues and hair in a death attributed to oral dothiepin (ProthiadenR) ingestion. The blood concentrati...detailed

Spectrophotometric and spectrofluorimetric methods for analysis of tramadol, acebutolol and DOTHIEPIN (cas 113-53-1) in pharmaceutical preparations08/24/2019

Sensitive spectrophotometric and spectrofluorimetric methods are described for the determination of tramadol, acebutolol and dothiepin (dosulepin) hydrochlorides. The two methods are based on the condensation of the cited drugs with the mixed anhydrides of malonic and acetic acids at 60 °C for ...detailed

Relevant articles and documents

DOTHIEPIN AND METHODS OF USING THE SAME TO TREAT SLEEP DISORDERS

The invention relates to dothiepin, metabolites of dothiepin, isomers of the same, and pharmaceutically-acceptable salts and prodrugs of the same; compositions containing the same, and the use of any of the aforementioned for the treatment of sleep disorders.