dimenhydrinate

Also 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.

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 Å²
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

Mass: 469.188

Show 5 more facts

chemical formula: C₂₄H₂₈ClN₅O₃
World Health Organisation international non-proprietary name: dimenhydrinate
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
stylized name: dimenhyDRINATE

Sources (3)

via Wikidata · CC0

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