Structure via PubChem · Public domain (PubChem)
dimenhydrinate
Sign in to saveAlso known as Dramamine, 8-chloro-1,3-Dimethyl-3,7-dihydro-1H-purine-2,6-dione - 2-(diphenylmethoxy)-N,N-dimethylethanamine (1, 1), Benzhydryl-beta-dimethylaminoethylether 8-chlorotheophylline, Diphenhydramine theoclate, N,N-Dimethyl-2-diphenylmethoxyethylamine 8-chlorotheophyllinate, (O-Benzhydryl(dimethylamino)ethanol) 8-chlorotheophyllinate, Diphenhydramine 8-chlorotheophylline
Dimenhydrinate, also known as diphenhydramine/8-chlorotheophylline salt and sold under the brand names Dramamine and Gravol, among others, is an over-the-counter medication used to treat motion sickness and nausea. Dimenhydrinate is a theoclate salt composed of diphenhydramine and 8-chlorotheophylline (a theophylline relative) in a 1:1 ratio.
OverviewAI-generated
Dimenhydrinate is a chemical compound with the formula C₂₄H₂₈ClN₅O₃. Its stylized name is dimenhyDRINATE. The substance is represented by the canonical SMILES string CN1C2=C(C(=O)N(C1=O)C)NC(=N2)Cl.CN(C)CCOC(C1=CC=CC=C1)C2=CC=CC=C2.
The International Union of Pure and Applied Chemistry name is 2-benzhydryloxy-N,N-dimethylethanamine;8-chloro-1,3-dimethyl-7H-purine-2,6-dione. It has a topological polar surface area of 81.8. The molecule contains one hydrogen bond donor and five hydrogen bond acceptors. In PubChem, it is identified by the CID 10660 and the InChIKey NFLLKCVHYJRNRH-UHFFFAOYSA-N.
Synthesized by Vinony from 12 facts across 3 sources: Wikidata, PubMed, PubChem. 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
- 459441657
- Drug.type
- combo
- Drug.image
- Dimenhydrinate.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 160
- Drug.component1
- Diphenhydramine
- Drug.class1
- Antihistamine, sedative
- Drug.component2
- 8-chlorotheophylline
- Drug.class2
- stimulant
- Drug.tradename
- Dramamine, Draminate, Gravol, others
- Drug.MedlinePlus
- a607046
- Drug.DailyMedID
- Dimenhydrinate
- Drug.pregnancy_AU
- A
- Drug.routes_of_administration
- By mouth, rectal, , intramuscular
- Drug.ATC_prefix
- R06
- Drug.ATC_suffix
- AA11
via Wikipedia infobox
Chemical data
- Formula
- C24H28ClN5O3
- Molecular weight
- 470 g/mol
- IUPAC name
- 2-benzhydryloxy-N,N-dimethylethanamine;8-chloro-1,3-dimethyl-7H-purine-2,6-dione
- SMILES
- CN1C2=C(C(=O)N(C1=O)C)NC(=N2)Cl.CN(C)CCOC(C1=CC=CC=C1)C2=CC=CC=C2
- InChIKey
- NFLLKCVHYJRNRH-UHFFFAOYSA-N
- Polar surface area
- 81.8 Ų
- H-bond donors
- 1
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Research
675 papers- Cinnarizine/dimenhydrinate for vertigo.Australian prescriber · 2021
- Misuse and dependence of dimenhydrinate: A mixed studies systematic review.Journal of psychiatric research · 2021
- Diphenhydramine, dimenhydrinate: misuse.Prescrire international · 2015
- Dimenhydrinate for prophylaxis of postoperative nausea and vomiting: a meta-analysis of randomized controlled trials.Acta anaesthesiologica Scandinavica · 2002
- Efficacy and safety of the cinnarizine/dimenhydrinate combination versus betahistine in the treatment of vertigo: A systematic literature review.Acta otorrinolaringologica espanola · 2025
via PubMed
Wikidata facts
- Subclass of
- combination drug
- Has part
- 8-chlorotheophylline
- Mass
- 469.188
- Has use
- medication
Show 8 more facts
- chemical formula
- C₂₄H₂₈ClN₅O₃
- World Health Organisation international non-proprietary name
- dimenhydrinate
- medical condition treated
- vomiting
- canonical SMILES
- CN1C2=C(C(=O)N(C1=O)C)NC(=N2)Cl.CN(C)CCOC(C1=CC=CC=C1)C2=CC=CC=C2
- Commons category
- Dimenhydrinate
- subject has role
- antiemetic
- side effect
- somnolence
- stylized name
- dimenhyDRINATE
Sources (3)
via Wikidata · CC0
~6 min read
Encyclopedic overview
11 sectionsContents
- Medical uses
- Side effects
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Recreational use
- History
- Brand names
- Popular culture
- References
- External links
Dimenhydrinate, also known as diphenhydramine/8-chlorotheophylline salt and sold under the brand names Dramamine and Gravol, among others, is an over-the-counter medication used to treat motion sickness and nausea. Dimenhydrinate is a theoclate salt composed of diphenhydramine and 8-chlorotheophylline (a theophylline relative) in a 1:1 ratio.
Dimenhydrinate was introduced to the market by G.D. Searle in 1949.
Excerpted from Wikipedia’s “dimenhydrinate” article, available under the CC BY-SA 4.0 licence.