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| CAS No.: | 1668-19-5 |
|---|---|
| Name: | DOXEPIN |
| Molecular Structure: | |
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| Formula: | C19H21 N O |
| Molecular Weight: | 279.382 |
| 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 |
| Density: | 1.122 g/cm3 |
| Melting Point: | 187-189°C |
| Boiling Point: | 413.3 °C at 760 mmHg |
| Flash Point: | 121.3 °C |
| Solubility: | readily soluble in water, lower |
| Appearance: | white crystalline solid |
| Hazard Symbols: | T |
| Risk Codes: | 25 |
| 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. |
| PSA: | 12.47000 |
| LogP: | 3.96240 |
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Chemistry
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
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.
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.
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.
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. |
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.
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).