Product Name

  • Name

    DOXEPIN

  • EINECS
  • CAS No. 1668-19-5
  • Article Data15
  • CAS DataBase
  • Density 1.122 g/cm3
  • Solubility readily soluble in water, lower
  • Melting Point 187-189°C
  • Formula C19H21 N O
  • Boiling Point 413.3 °C at 760 mmHg
  • Molecular Weight 279.382
  • Flash Point 121.3 °C
  • Transport Information
  • Appearance white crystalline solid
  • Safety Human poison by ingestion. Experimental poison by ingestion, intravenous, and intraperitoneal routes. A sedative and hypnotic used as an antianxiety agent. When heated to decomposition it emits toxic fumes of NOx.
  • Risk Codes 25
  • Molecular Structure Molecular Structure of 1668-19-5 (DOXEPIN)
  • Hazard Symbols T
  • Synonyms Dibenz[b,e]oxepin-D11(6H),g-propylamine, N,N-dimethyl-(7CI,8CI); Dibenz[b,e]oxepin, 1-propanamine deriv.;11-[3-(Dimethylamino)propylidene]-6H-dibenz[b,e]oxepin; Doxepin; Doxepine;N,N-Dimethyldibenz[b,e]oxepin-D11(6H),g-propylamine;NSC 108160
  • PSA 12.47000
  • LogP 3.96240

Doxepin Chemical Properties

IUPAC Name: (3Z)-3-(6H-Benzo[c][1]benzoxepin-11-ylidene)-N,N-dimethylpropan-1-amine
The MF of Doxepin (CAS NO.1668-19-5) is C19H21NO.

                     
The MW of Doxepin (CAS NO.1668-19-5) is 279.38.
Synonyms of Doxepin (CAS NO.1668-19-5): (3Z)-3-Dibenzo[b,E]oxepin-11(6H)-ylidene-N,N-dimethyl-1-propanamine ; 11-(3-(Dimethylamino)propylidene)-6H-dibenz(B,E)0xepine
Product Categories: Heterocyclic Compounds;Neurochemicals
Apperance: oil liquid
Index of Refraction: 1.629 
Density: 1.122 g/ml 
Flash Point: 121.3 °C
Boiling Point: 413.3 °C
Melting Point: 187-189 °C

Doxepin History

 Doxepin was synthesized by Stach and Spingler from the German drug manufacturer C. F. Boehringer & Söhne GmbH in Mannheim. It was tested from 1963 to 1968 in different German and Swiss psychiatric institutions and was approved in Germany and elsewhere thereafter. The antidepressive effects were found to be excellent. Strong anxiolytic and sedative properties were also demonstrated. Doxepin has been in clinical use for several decades. The drug plays an important role in many indications today, not only in psychiatry/neurology.

Doxepin Uses

  Doxepin (CAS NO.1668-19-5) is antidepressant used clinically to treat anxiety and depression.As doxepin hydrochloride, it is the active ingredient in cream-based preparations (Zonalon and Xepin) for the treatment of dermatological itch. Doxepin is currently investigated for the treatment of insomnia.

Doxepin Production

 Triphenyl phosphine and 1,3-dibromo-propane generated 3-bromo-propyl bromide, triphenyl phosphine.To continue with the reaction of anhydrous dimethylamine obtained 3-dimethylamino-propyl bromide, benzene, hydrogen-3 phosphonium salt , and then with the 6,11 - dihydro-dibenzo [b, e] evil G -11 - ketones obtained doxepin. Intermediate 6,11 - dihydro-dibenzo [b, e] evil G -11 - one of the synthetic method can be found in Belg.pat, 641498.

Doxepin Toxicity Data With Reference

1.    

orl-hmn LDLo:60 mg/kg

    CTOXAO    Clinical Toxicology. 10 (1977),327.
2.    

orl-rat LD50:147 mg/kg

    ARZNAD    Arzneimittel-Forschung. Drug Research. 15 (1965),863.
3.    

ipr-rat LD50:182 mg/kg

    ARZNAD    Arzneimittel-Forschung. Drug Research. 15 (1965),863.
4.    

ivn-rat LD50:16 mg/kg

    ARZNAD    Arzneimittel-Forschung. Drug Research. 15 (1965),863.
5.    

orl-mus LD50:135 mg/kg

    ARZNAD    Arzneimittel-Forschung. Drug Research. 15 (1965),863.
6.    

ipr-mus LD50:79 mg/kg

    ARZNAD    Arzneimittel-Forschung. Drug Research. 15 (1965),863.
7.    

ivn-mus LD50:26 mg/kg

    ARZNAD    Arzneimittel-Forschung. Drug Research. 15 (1965),863.
8.    

ivn-rbt LD50:11 mg/kg

    ARZNAD    Arzneimittel-Forschung. Drug Research. 15 (1965),863.

Doxepin Safety Profile

Human poison by ingestion. Experimental poison by ingestion, intravenous, and intraperitoneal routes. A sedative and hypnotic used as an antianxiety agent. When heated to decomposition it emits toxic fumes of NOx.

Doxepin Specification

 Doxepin is a psychotropic agent with tricyclic antidepressant and anxiolytic properties, known under many brand-names such as Aponal, the original preparation by Boehringer-Mannheim, now part of the Roche group; Adapine, Deptran, Sinquan and Sinequan (Pfizer).

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