Structure via PubChem · Public domain (PubChem)
doxylamine
Sign in to saveAlso known as phenyl-2-pyridylmethyl-beta-N,N-dimethylaminoethyl ether, N,N-dimethyl-2-[1-phenyl-1-(2-pyridinyl)ethoxy]ethanamine, 2-dimethylaminoethoxyphenylmethyl-2-picoline, 2-{alpha-[2-(dimethylamino)ethoxy]-alpha-methylbenzyl}pyridine
Doxylamine is an antihistamine medication used to treat insomnia and allergies, and—in combination with pyridoxine (vitamin B6)—to treat morning sickness in pregnant women. It is available over-the-counter and is sold under such brand names as Equate or Unisom, among others; and it is used in nighttime cold medicines (e.g., NyQuil) and pain medications containing paracetamol (acetaminophen) or codeine to help with sleep. The medication is delivered chemically by the salt doxylamine succinate and is taken by mouth. Doxylamine and other first-generation antihistamines are the most widely used sl
Key facts
- Drug.ATC_suffix
- AA09
- Drug.PubChem
- 3162
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 456483386
- Drug.IUPAC_name
- (RS)-N,N-dimethyl-2-[1-phenyl-1-(pyridin-2-yl)ethoxy]ethan-1-amine
- Drug.image
- Doxylamine structure.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 200px
- Drug.alt
- Skeletal formula of the doxylamine molecule
- Drug.image2
- Doxylamine 3D ball.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 200px
- Drug.alt2
- Ball-and-stick model of the doxylamine molecule
- Drug.tradename
- Unisom, Vicks Formula 44 (in combination with dextromethorphan), others
- Drug.MedlinePlus
- a682537
- Drug.pregnancy_US
- B
- Drug.pregnancy_AU
- A
- Drug.pregnancy_category
- A (Briggs)
via Wikipedia infobox
Chemical data
- Formula
- C17H22N2O
- Molecular weight
- 270.37 g/mol
- IUPAC name
- N,N-dimethyl-2-(1-phenyl-1-pyridin-2-ylethoxy)ethanamine
- SMILES
- CC(C1=CC=CC=C1)(C2=CC=CC=N2)OCCN(C)C
- InChIKey
- HCFDWZZGGLSKEP-UHFFFAOYSA-N
- XLogP
- 2.5
- Polar surface area
- 25.4 Ų
- H-bond donors
- 0
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
585 papersvia PubMed
Wikidata facts
- Mass
- 270.173213
Show 5 more facts
- chemical formula
- C₁₇H₂₂N₂O
- canonical SMILES
- CC(C1=CC=CC=C1)(C2=CC=CC=N2)OCCN(C)C
- World Health Organisation international non-proprietary name
- doxylamine
- Commons category
- Doxylamine
- defined daily dose
- 25
via Wikidata · CC0
~12 min read
Article
15 sectionsContents
- Medical uses
- Insomnia
- Morning sickness
- Available forms
- Contraindications
- Side effects
- Overdose
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Chemistry
- History
- Society and culture
- Formulations
- References
Doxylamine is an antihistamine medication used to treat insomnia and allergies, and—in combination with pyridoxine (vitamin B6)—to treat morning sickness in pregnant women. It is available over-the-counter and is sold under such brand names as Equate or Unisom, among others; and it is used in nighttime cold medicines (e.g., NyQuil) and pain medications containing paracetamol (acetaminophen) or codeine to help with sleep. The medication is delivered chemically by the salt doxylamine succinate and is taken by mouth. Doxylamine and other first-generation antihistamines are the most widely used sleep medications in the world. Typical side effects of doxylamine include dizziness, drowsiness, grogginess, and dry mouth, among others.
As an antihistamine, doxylamine is an inverse agonist of the histamine H1 receptor. As a first-generation antihistamine, it typically crosses the blood–brain barrier into the brain, thereby producing a suite of sedative and hypnotic effects that are mediated by the central nervous system.