Doxepin
Also called Silenor.
A tricyclic antidepressant, now more often prescribed at low strength for insomnia and for itching. Doxepin (C19H21NO, 279 g/mol) is a tricyclic antidepressant dispensed on prescription.
Sources and notes
- The introductionfrom sourceMoleculeFinder curated
- Other namesfrom sourceWikidataIts English label and aliases on Wikidata.
- Formula and weightcomputedPubChem
- 2D drawingcomputedPubChem structure, drawn by RDKit
- 3D modelfrom sourcePubChem 3D conformerLoaded after the page has painted, and on a phone only when you ask for it; the 2D drawing shows until it arrives.
Where you encounter it
Dispensed on prescription, not sold on a shelf. Doxepin on the product labels we hold.
Medicines
Every product and list we hold
Sources and notes
- The product labels and their strengthsfrom sourceDailyMed (FDA label)Each label lists the molecule as an ingredient, and an active ingredient at the strength shown.
- How it gets therefrom sourceMoleculeFinder curatedEach mark is set by hand on our lists, never inferred; a label's ingredient is added by the maker. A row with no mark data says Not marked.
- The line abovefrom sourceMoleculeFinder curatedFrom the group the molecule belongs to.
Explore its structure
Choose a part to light it up.
A nitrogen bonded to three carbons, with no hydrogen of its own. Its spare pair of electrons can still pick up a hydrogen ion, so a tertiary amine is a base.
From: standard chemistry.
An oxygen bridging two carbons, written C-O-C. It accepts hydrogen bonds but has no hydrogen to give, and it is slow to react.
From: standard chemistry.
Rings joined where they share atoms, or a single ring standing alone. Atoms in a ring are held in place, so this part keeps its shape while chains around it can bend.
From: standard chemistry.
Sources and notes
- The drawingcomputedPubChem structure, drawn by RDKitThe page's one shipped drawing, with the chosen part lit in amber under it.
- The partscomputedFound by ruleEach part is found by a chemical pattern, never picked by hand atom by atom; its words say where they come from.
Properties and sources
Calculated by PubChem
- Molecular formula
- C19H21NO
- Molecular weight
- 279.4 g/mol
- XLogP3octanol/water, log units
- 4.3
- Polar surface areatopological
- 12.5 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Rotatable bonds
- 3
- Complexity
- 363
Measured LD50, HSDB via PubChem
147 mg/kg pure doxepin, rat, oral
An LD50 is an animal study measurement, not a dose for a person.
Reported Licence
The US Food and Drug Administration licenses Doxepin for human use (NDA 020126, authorized April 1, 1994), as Zonalon. Drugs@FDA
Groups it belongs to
- Category
- Prescription medicine
- Elements
- Nitrogen
CN(C)CCC=C1C2=CC=CC=C2COC3=CC=CC=C31PubChem CID 3158 · Wikidata Q71704041 · InChIKey ODQWQRRAPPTVAG-UHFFFAOYSA-N · Data refreshed
Questions
- What is Doxepin?
- A tricyclic antidepressant, now more often prescribed at low strength for insomnia and for itching. Doxepin (C19H21NO, 279 g/mol) is a tricyclic antidepressant dispensed on prescription.
- How toxic is Doxepin?
- The reported LD50 of Doxepin is 147 mg/kg (rat, oral). An LD50 is an animal study measurement, not a dose for a person. from source
- What kind of molecule is Doxepin?
- Doxepin has the formula C19H21NO and a molecular weight of 279.4 g/mol. MoleculeFinder files it under tricyclic antidepressants, in the prescription medicine group. from sourcefrom sourcefrom sourcefrom source
- What else is Doxepin called?
- Doxepin is also called Silenor. from source
- Who licenses Doxepin as a medicine?
- The US Food and Drug Administration licenses Doxepin for human use (NDA 020126, authorized April 1, 1994), as Zonalon. from source
Sources and notes
- Calculated valuescomputedPubChemComputed from the structure, so no laboratory conditions apply; complexity is PubChem's own structural score.
- LD50from sourceHSDB via PubChemOther values the sources report: mouse, oral, 135 mg/kg; rat, intravenous, 16 mg/kg; rat, another route, 182 mg/kg. The page shows the one LD50 the site uses everywhere.
- Licencefrom sourceDrugs@FDARead 2026-10-21.
- Data refreshedfrom sourceMoleculeFinder2026-11-09
Keep exploring
Sources and notes
- The same kind of moleculefrom sourceMoleculeFinder curated groupsA structural neighbour in the same family or type group; the line names the group in its own words.
- Similar in shapecomputedRDKit Morgan/TanimotoNeighbours by structural fingerprint; the sentence names the chemical groups the two share.
- The drawingscomputedPubChem structures, drawn by RDKit