Dimenhydrinate
Dimenhydrinate.svg
Combination of
DiphenhydramineAntihistamine
8-chlorotheophyllinestimulant
Clinical data
Trade namesDramamine, Draminate, Gravol, others
AHFS/Drugs.comMonograph
MedlinePlusa607046
Pregnancy
category
  • AU: A
Routes of
administration
Oral, rectal, intravascular, intramuscular
ATC code
Legal status
Legal status
  • AU: S2 (Pharmacy medicine)
  • CA: OTC
  • US: OTC
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.007.593 Edit this at Wikidata
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Dimenhydrinate, sold under the brand name Dramamine, among others, is an over-the-counter drug used to treat motion sickness and nausea. Dimenhydrinate is a theoclate salt composed of diphenhydramine, an ethanolamine derivative, and 8-chlorotheophylline, a chlorinated theophylline derivative, in a 1 : 1 ratio.[1]

Medical uses

Nausea

Dimenhydrinate is an over-the-counter (OTC) antihistamine indicated for the prevention and relief of nausea and vomiting from a number of causes. It is an H1 receptor antagonist that demonstrates anticholinergic activity.[2]

Medicinal chemistry

Diphenhydramine is the primary constituent of dimenhydrinate and dictates the primary effect. The main difference relative to pure diphenhydramine is a lower potency due to being combined with 8-chlorotheophylline. By weight, dimenhydrinate is between 53% to 55.5% diphenhydramine.[3]

Side effects

Common side effects may include:[4]

Recreational use

Dimenhydrinate is recreationally used as a deliriant.[5][6][7] Slang terms for Dramamine used this way include "drama", "dime", "dime tabs", "D-Q", "substance D", "d-house", and "drams".[8] Abusing Dramamine is sometimes referred to as Dramatizing or "going a dime a dozen", a reference to the amount of Dramamine tablets generally necessary for a trip.[9]

Many users report a side-effect profile consistent with tropane alkaloid (e.g. atropine) poisoning as both show antagonism of muscarinic acetylcholine receptors in both the central and autonomic nervous system, which inhibits various signal transduction pathways.[6]

Other CNS effects occur within the limbic system and hippocampus, causing confusion and temporary amnesia due to decreased acetylcholine signaling. Toxicology also manifests in the autonomic nervous system, primarily at the neuromuscular junction, resulting in ataxia and extrapyramidal side effects and the feeling of heaviness in the legs, and at sympathetic post-ganglionic junctions, causing urinary retention, pupil dilation, tachycardia, irregular urination, and dry red skin caused by decreased exocrine gland secretions, and mucous membranes. Considerable overdosage can lead to myocardial infarction (heart attack), serious ventricular arrhythmias, coma, and death.[10] Such a side effect profile is thought to give ethanolamine-class antihistamines a relatively low abuse liability.[citation needed] An antidote that can be used for dimenhydrinate poisoning is physostigmine.[11]

Brand names

Dimenhydrinate is marketed under many brand names: in the US, Mexico, Turkey and Serbia as Dramamine; in Ukraine as Driminate; in Canada, Costa Rica, and India as Gravol; in Iceland as Gravamin; in Russia and Croatia as Dramina; in South Africa and Germany as Vomex; in Australia and Austria as Vertirosan; in Brazil as Dramin; in Colombia as Mareol; in Ecuador as Anautin; in Hungary as Daedalon; in Indonesia as Antimo; in Italy as Xamamina or Valontan; in Peru as Gravicoll; in Poland and Slovakia as Aviomarin;[12] in Portugal as Viabom, Vomidrine, and Enjomin; in Spain as Biodramina; in Thailand as Daimenin; in Israel as Travamin; in Pakistan as Gravinate; and in Ethiopia as dimenhydrinate.[13]

Popular culture

Modest Mouse produced a song titled "Dramamine" on their 1996 debut album This Is a Long Drive for Someone with Nothing to Think About. The song uses side effects of the drug as a metaphor for the deteriorating state of a personal relationship.[14]

References

  1. ^ Hemmings, Hugh C., Jr.; Talmage, Egan D., eds. (2019). Pharmacology and Physiology for Anesthesia (Second Edition) (2nd ed.). Elsevier Inc. pp. 671–692. ISBN 978-0-323-48110-6. Retrieved 2 August 2022.
  2. ^ Canadian Agency for Drugs and Technologies in Health (2015). "Abuse and Misuse Potential of Dimenhydrinate: A Review of the Clinical Evidence [Internet]". CADTH Rapid Response Reports. PMID 26985532.((cite journal)): CS1 maint: uses authors parameter (link)
  3. ^ "Dimenhydrinate injection, solution". Daily Med. U.S. National Library of Medicine. Archived from the original on 13 October 2014. Retrieved 19 July 2014.))
  4. ^ "Dimenhydrinate". Drugs.com. Archived from the original on 28 May 2004.
  5. ^ "The Health Risks of Abusing Motion sickness pills". Narconon International. Retrieved 13 September 2016.
  6. ^ a b Lessenger JE, Feinberg SD (2008). "Abuse of prescription and over-the-counter medications". Journal of the American Board of Family Medicine. 21 (1): 45–54. doi:10.3122/jabfm.2008.01.070071. PMID 18178702.
  7. ^ Gardner DM, Kutcher S (March 1993). "Dimenhydrinate abuse among adolescents". Canadian Journal of Psychiatry. 38 (2): 113–6. doi:10.1177/070674379303800208. PMID 8467436. S2CID 30190588.
  8. ^ "The Dangers of Dimenhydrinate Abuse". Bright Hub. 6 October 2009. Retrieved 13 September 2016.
  9. ^ "Dramamine". Budderbongs forums. Retrieved 13 September 2016.
  10. ^ "Are Teens Abusing Motion Sickness Pills? - Muir Wood Adolescent and Family Services". Archived from the original on 18 September 2016. Retrieved 13 September 2016.
  11. ^ Scharman, Elizabeth (19 January 2006). "Diphenhydramine and Dimenhydrinate Poisoning: an Evidence-Based Consensus Guideline for Out-of-Hospital Management". Clinical Toxicology. 44 (3): 205–223. doi:10.1080/15563650600585920. PMID 16749537. S2CID 702353.
  12. ^ "Aviomarin, tabletki, 50 mg, 5 szt". Dox.pl (in Polish).
  13. ^ "Gravinate [Dimenhydrinate]". Karachi Pakistan: The Searle Company. Archived from the original on 5 May 2013.
  14. ^ "Modest Mouse: 'This is a long drive...'". Portland. Retrieved 26 March 2019: Glacial Pace Recordings.((cite web)): CS1 maint: location (link)