File:Diphenhydramine_2D_skeletal.svg · Wikimedia Commons · See Wikimedia Commons
diphenhydramine
Sign in to saveAlso known as Benadryl®, benzhydramine, dimehydrinate, O-benzhydryldimethylaminoethanol, 2-diphenylmethoxy-N,N-demthylethanamine, beta-dimethylaminoethyl benzhydryl ether, alpha-(2-dimethylaminoethoxy)diphenylmethane, N-(2-(diphenylmethoxy)ethyl)-N,N-dimethylamine
Diphenhydramine, sold under the brand name Benadryl among others, is an antihistamine and sedative. Although generally considered sedating, diphenhydramine can cause paradoxical central nervous system stimulation in some individuals, particularly at higher doses. This may manifest as agitation, anxiety, or restlessness rather than sedation. It is a first-generation H1-antihistamine and it works by blocking certain effects of histamine, which produces its antihistamine and sedative effects. Diphenhydramine is also a potent anticholinergic. It is mainly used to treat allergies, insomnia, and sym
OverviewAI-generated
Diphenhydramine is a chemical compound with the formula C₁₇H₂₁NO. Its IUPAC name is 2-benzhydryloxy-N,N-dimethylethanamine. The substance has a mass of 255.162 and a weight of 255.35. It features a defined daily dose of 200. The stylized name for the compound is diphenhydrAMINE.
Chemical properties include an xlogp value of 3.3 and a topological polar surface area of 12.5. The molecule contains zero hydrogen bond donors and two hydrogen bond acceptors, with a charge of 0. Its canonical SMILES notation is CN(C)CCOC(C1=CC=CC=C1)C2=CC=CC=C2.
In literature, diphenhydramine is associated with 6,920 PubMed entries. The subject is referenced by 2,230 other encyclopedia articles.
Synthesized by Vinony from 19 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
Key facts
- Drug.Verifiedfields
- changed
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 460791686
- Drug.image
- Diphenhydramine 2D skeletal.svg
- Drug.image_class
- skin-invert-image
- Drug.image2
- Diphenhydramine_3D-Ball-and-Stick.png
- Drug.image_class2
- 225
- Drug.tradename
- Benadryl, others
- Drug.MedlinePlus
- a682539
- Drug.DailyMedID
- Diphenhydramine
- Drug.pregnancy_AU
- A
- Drug.dependency_liability
- Low
- Drug.routes_of_administration
- By mouth, intramuscular, intravenous, topical, rectal
- Drug.class
- First-generation antihistamine, antimuscarinic, hallucinogen (deliriant)
- Drug.ATC_prefix
- D04
- Drug.ATC_suffix
- AA32
- Drug.ATC_supplemental
- ,
- Drug.legal_AU
- S4
via Wikipedia infobox
Chemical data
- Formula
- C17H21NO
- Molecular weight
- 255.35 g/mol
- IUPAC name
- 2-benzhydryloxy-N,N-dimethylethanamine
- SMILES
- CN(C)CCOC(C1=CC=CC=C1)C2=CC=CC=C2
- InChIKey
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N
- XLogP
- 3.3
- Polar surface area
- 12.5 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Research
6,920 papers- Diphenhydramine Use in End-Stage Kidney Disease.American journal of therapeutics · 2021
- Diphenhydramine.American pharmacy · 1986
- Diphenhydramine: Time to Move on?The journal of allergy and clinical immunology. In practice · 2022
- Diphenhydramine overdose with neuromuscular excitation.Clinical toxicology (Philadelphia, Pa.) · 2022
- Diphenhydramine photoallergy.Archives of dermatology · 1974
via PubMed
~20 min read
Encyclopedic overview
24 sectionsContents
- Medical uses
- Allergies
- Movement disorders
- Sleep
- Nausea
- Anxiety
- Contraindications
- Adverse effects
- Special populations
- Overdose
- Interactions
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Chemistry
- Detection in body fluids
- History
- Society and culture
- Marketing
- Cultural impact
- Recreational use
- References
- Further reading
- External links
Diphenhydramine, sold under the brand name Benadryl among others, is an antihistamine and sedative. Although generally considered sedating, diphenhydramine can cause paradoxical central nervous system stimulation in some individuals, particularly at higher doses. This may manifest as agitation, anxiety, or restlessness rather than sedation. It is a first-generation H1-antihistamine and it works by blocking certain effects of histamine, which produces its antihistamine and sedative effects. Diphenhydramine is also a potent anticholinergic. It is mainly used to treat allergies, insomnia, and symptoms of the common cold. It is also less commonly used for tremors in parkinsonism, and nausea. It is taken by mouth, injected into a vein, injected into a muscle, or applied to the skin. Maximal effect is typically around two hours after a dose, and effects can last for up to seven hours.
Common side effects include sleepiness, poor coordination, and an upset stomach. There is no clear risk of harm when used during pregnancy; however, use during breastfeeding is not recommended.
Excerpted from Wikipedia’s “diphenhydramine” article, available under the CC BY-SA 4.0 licence.