Doxepin hydrochloride

Base Information

• Chemical Name: Doxepin hydrochloride
• CAS No.: 1229-29-4
• Deprecated CAS: 20917-44-6,25197-84-6
• Molecular Formula: C19H22ClNO
• Molecular Weight: 315.843
• Hs Code.: 29329990
• European Community (EC) Number: 214-966-8
• UNII: CU61C5RH24
• DSSTox Substance ID: DTXSID8045145
• Wikidata: Q27275787
• NCI Thesaurus Code: C29006
• RXCUI: 203179
• ChEMBL ID: CHEMBL1200462
• Mol file: 1229-29-4.mol

Synonyms:1-Propanamine,3-dibenz[b,e]oxepin-11(6H)-ylidene-N,N-dimethyl-, hydrochloride (9CI);Dibenz[b,e]oxepin-D11(6H),g-propylamine, N,N-dimethyl-, hydrochloride (7CI,8CI);Dibenz[b,e]oxepin, 1-propanamine deriv.;Adapin;Aponal;Curatin;Doxepinhydrochloride;N,N-Dimethyldibenz[b,e]oxepin-D11(6H),g-propylaminehydrochloride;P 3693A;Quitaxon;Silenor;Sinequan;Sinequin;Doxepin HCl;1-Propanamine,3-(dibenz[b,e]oxepin-11(6H)-ylidene)-N,N-dimethyl-, hydrochloride (1:1);

Chemical Property of Doxepin hydrochloride

Chemical Property:

• Appearance/Colour: white to off-white powder
• Vapor Pressure: 4.87E-07mmHg at 25°C
• Melting Point: 187-189°C
• Boiling Point: 413.3 °C at 760 mmHg
• Flash Point: 121.3 °C
• PSA: 12.47000
• LogP: 4.76440
• Storage Temp.: 2-8°C
• Solubility.: 1 M HCl: 50 mg/mL
• Water Solubility.: Soluble in water (100 mM), chloroform (1:2), alcohol (1:1), methanol, and DMSO.
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 315.1389920
• Heavy Atom Count: 22
• Complexity: 363

Purity/Quality:

98% up, ^*data from raw suppliers

Doxepin hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T,F
• Statements: 25-39/23/24/25-23/24/25-11
• Safety Statements: 36/37/39-45-36/37-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN(C)CCC=C1C2=CC=CC=C2COC3=CC=CC=C31.Cl
• Isomeric SMILES: CN(C)CC/C=C/1\C2=CC=CC=C2COC3=CC=CC=C31.Cl
• Recent ClinicalTrials: Stigma and Efficacy of Zhizhu Kuanzhong Capsules
• Recent EU Clinical Trials: Pharmacovigilance in children and adolescents:
• Description: 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.
• Uses: Doxepin is used clinically to treat anxiety and depression. Doxepin is an antidepressant. 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. Used clinically to treat anxiety and depression. Antidepressant.
• Indications: Doxepin (Sinequan, Adapin) is a tricyclic antidepressant with potent H1 and H2 antagonistic effects. It also has antimuscarinic, antiserotonic, and anti-α-adrenergic activity. Use of 10 to 50 mg PO t.i.d. to q.i.d. has been shown to be effective in the treatment of primary acquired, chronic idiopathic urticaria, idiopathic cold urticaria, and for patients with anxiety or depression associated with their urticaria. Sedation and dry mouth are the most common side effects. Doxepin may interact with other drugs that are metabolized by the cytochrome P-450 system (ketoconazole, itraconazole, erythromycin, clarithromycin, etc.).
• Therapeutic Function: Tranquilizer

Technology Process of Doxepin hydrochloride

There total 25 articles about Doxepin hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.23%

doxepin (1668-19-5,3607-18-9,3607-34-9) → doxepin hydrochloride (1229-29-4,25127-31-5)

Guidance literature:

With hydrogenchloride; In ethanol; at 150 ℃; for 22h; Temperature;

Reference yield:

2-(phenoxymethyl)benzoic acid (724-98-1) → doxepin hydrochloride (1229-29-4,25127-31-5)

Guidance literature:

Multi-step reaction with 2 steps

1: P₂O₅ / ethanol

2: 2.) conc. HCl, 3.) HCl-gas / 1.) THF, toluene, 65 deg C, 2 h, 2.) 1 h, 3.) 75 deg C, 1.5 h, ethanol

With hydrogenchloride; phosphorus pentoxide; In ethanol;

Reference yield:

3-(N,N-dimethylamino)propylmagnesium chloride (19070-16-7) + 6,11-dihydrodibenz[b,e]oxepin-11-one (4504-87-4) → doxepin hydrochloride (1229-29-4,25127-31-5)

Guidance literature:

With hydrogenchloride; Multistep reaction; 1.) THF, toluene, 65 deg C, 2 h, 2.) 1 h, 3.) 75 deg C, 1.5 h, ethanol;

upstream raw materials:

doxepin hydrochloride

6,11-dihydrodibenz[b,e]oxepin-11-one

3-(Dimethylamino)propyl chloride

2-benzofuran-1(3H)-one

Downstream raw materials:

6,11-dihydrodibenz[b,e]oxepin-11-one

(E)-N-desmethyl-N-formyldoxepin

(E)-N-acetyldidesmethyldoxepin

(E)-N-acetyl-N-desmethyldoxepin

Refernces

• 1、 -. "Improved synthesis method of doxepin hydrochloride". Paragraph 0056-0061; 0084-0089. . Retrieved 2021/11/19.
• 2、 Jiang, Hongshuo,Mao, Guijie,Wu, Hongfeng,An, Qi,Zuo, Minghui,Guo, Weihao,Xu, Chunzhao,Sun, Zhizhong,Chu, Wenyi. "Synthesis of dibenzocycloketones by acyl radical cyclization from aromatic carboxylic acids using methylene blue as a photocatalyst". supporting information. p. 5368 - 5373. Retrieved 2019/10/11.