3-Dibenz(b,e)oxepin-11(6H)-yliden-N,N-dimethyl-1-propanamin-hydrochlorid
DOXEPIN HCL · Sinequan · DOXEPINe HCL · p-4599 · adapin · Toruan · Novoxapin · TIMTEC-BB SBB005916
Identifikatoren & physikalische Daten
| CAS No. | 1229-29-4 |
|---|---|
| Summenformel | C19H22ClNO |
| Durchschnittliche Molmasse | 315,8 g/mol |
| SMILES | CN(C)CCC=C1c2ccccc2COc2ccccc21.Cl |
| InChIKey | MHNSPTUQQIYJOT-UHFFFAOYSA-N |
| PubChem CID | 14675 |
| ChEMBL | CHEMBL1628234 |
| Lokaler Name | 3-Dibenz(b,e)oxepin-11(6H)-yliden-N,N-dimethyl-1-propanamin-hydrochlorid |
Chemische & physikalische Eigenschaften
| Polarare Oberfläche (TPSA) | 12,5 |
|---|---|
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 22 |
| Formalladung | 0 |
| Komplexität | 363 |
| Schmelzpunkt | 187-189°C |
| Flammpunkt | 9℃ |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | 1 M HCl: 50 mg/mLSoluble in water (100 mM), chloroform (1:2), alcohol (1:1), methanol, and DMSO. |
| Aggregatzustand | powder |
| Farbe | white to off-white |
| Merck | 14,3435 |
| Stabilität | Store in Freezer at -20°C |
| InChI | InChI=1S/C19H21NO.ClH/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,7,13-14H2,1-2H31H/b17-11+ |
| InChIKey | MHNSPTUQQIYJOT-SJDTYFKWSA-N |
| SMILES | C1(=C/CCN(C)C)\C2C=CC=CC=2OCC2C=CC=CC\1=2.Cl |
| CAS Datenbank | 1229-29-4(CAS DataBase Reference) |
Sicherheit & Vorschriften
| Wassergefährdungsklasse (WGK) | 3 |
|---|---|
| UN-Transportnummer | UN 2811 6.1/PG 3 |
| Zollcode | 29329990 |
| RTECS-Nr. | HQ4375000 |
| R-Sätze (R) | 25-39/23/24/25-23/24/25-11 |
| Toxizität | LD50 oral in rat: 147mg/kg |
| Gefahrensymbole | T,F |
| Sicherheitshinweise (S) | 36/37/39-45-36/37-16 |
| Gefahrenklasse | 6.1(b)Acute Tox. 3 Oral |
| Verpackungsgruppe | III |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
Anwendungen & Verwendung
Beschreibung
Doxepin is a tricyclic antidepressant that binds to the serotonin (5-HT) transporter (SERT) and norepinephrine transporter (NET; Kds = 68 and 29.5 nM, respectively). It is a histamine H1 receptor antagonist (Ki = 1.23 nM). Doxepin selectively binds to SERT and NET over the dopamine transporter (DAT; Kd = 12,100 nM) and inhibits histamine H1 over H2, H3, and H4 receptors (Kis = 170, 39,810, and 15,135 nM, respectively). It also binds to the 5-HT2 receptor, as well as to muscarinic acetylcholine and α1-adrenergic receptors (α1-ARs; Kds = 27, 23, and 23.5 nM, respectively). Doxepin (10 mg/kg, i.p.) decreases allodynia and hyperalgesia in a mouse model of chronic constriction injury-induced neuropathic pain. It increases the distance traveled in the center of the open field test and reduces immobility time in the forced swim test in a mouse model of depression induced by chronic stress when administered orally at a dose of 15 mg/kg. Formulations containing doxepin have been used in the treatment of depression and insomnia.
Verwenden
Doxepin hydrochloride is a tricyclic antidepressant that inhibits the reuptake of serotonin and norepinephrine and acts as an antagonist at histamine, serotonin, adrenergic, and muscarinic receptors with Ki values in the nanomolar range.It is a antidepressant used clinically to treat anxiety and depression.