Chemicals and Drugs

Doxepin

A dibenzoxepin tricyclic compound. It displays a range of pharmacological actions including maintaining adrenergic innervation. Its mechanism of action is not fully understood, but it appears to block reuptake of monoaminergic neurotransmitters into presynaptic terminals. It also possesses anticholinergic activity and modulates antagonism of histamine H(1)- and H(2)-receptors.

National Library of MedicineMedical Subject Headings2026

Structured Summary

Abstract

A dibenzoxepin tricyclic compound. It displays a range of pharmacological actions including maintaining adrenergic innervation. Its mechanism of action is not fully understood, but it appears to block reuptake of monoaminergic neurotransmitters into presynaptic terminals. It also possesses anticholinergic activity and modulates antagonism of histamine H(1)- and H(2)-receptors.

Chemical Identity

Chemical Information

Molecular Formula
C19H21NO
Molecular Weight
279.4 g/mol
CAS Registry No.
1668-19-5
IUPAC Name
3-(6H-benzo[c][1]benzoxepin-11-ylidene)-N,N-dimethylpropan-1-amine
InChIKey
ODQWQRRAPPTVAG-UHFFFAOYSA-N
SMILES
CN(C)CCC=C1C2=CC=CC=C2COC3=CC=CC=C31
MeSH Unique ID
D004316
Source
PubChem CID 3158

MeSH Record

Classification

Broader headings

Related Concepts

Knowledge Graph

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Drug Class

Pharmacological Action

MeSH Record

Synonyms

24 entry terms
  • Apo-Doxepin
  • Aponal
  • Deptran
  • Desidox
  • Doneurin
  • Doxepia
  • Doxepin Hydrochloride
  • Doxepin Hydrochloride, Cis-Trans Isomer Mixture (approximately 1:5)
  • Doxepin beta
  • Doxepin-RPh
  • Espadox
  • Mareen
  • Novo-Doxepin
  • Prudoxin
  • Quitaxon
  • Sinequan
  • Sinquan
  • Xepin
  • Zonalon
  • Apo Doxepin
  • ApoDoxepin
  • Doxepin RPh
  • Hydrochloride, Doxepin
  • Novo Doxepin

MeSH Record

Aspects Covered

25 allowable subheadings

Indexed with the subheadings administration & dosage, adverse effects, agonists, analogs & derivatives, analysis, antagonists & inhibitors, blood, cerebrospinal fluid, chemical synthesis, chemistry, classification, economics, history, immunology, isolation & purification, metabolism, pharmacokinetics, pharmacology, poisoning, radiation effects, standards, supply & distribution, therapeutic use, toxicity, urine.

MeSH Record

History Note

74

MeSH Hierarchy

Tree Numbers

  1. D02w.355w.291.852.500w
  2. D03w.633.300.382w.393w

AMA Style

References

  1. National Library of Medicine. Doxepin. Medical Subject Headings (MeSH). 2026. Unique ID D004316. http://id.nlm.nih.gov/mesh/2026/D004316
  2. Doxepin. In: Wikipedia. https://en.wikipedia.org/wiki/Doxepin
  3. Doxepin. In: Wikidata. https://www.wikidata.org/wiki/Q71704041
  4. Doxepin. In: PubChem Compound. CID 3158. https://pubchem.ncbi.nlm.nih.gov/compound/3158