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Dimenhydrinate

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Not to be confused with diphenhydramine.
"Dramamine" redirects here. For other uses, see Dramamine (disambiguation).

Dimenhydrinate
Combination of
DiphenhydramineAntihistamine, sedative
8-chlorotheophyllineStimulant
Clinical data
Trade namesDramamine, Draminate, Gravol, others
Other namesDiphenhydramine/8-chlorotheophylline salt
AHFS/Drugs.comMonograph
MedlinePlusa607046
License data
Pregnancy
category
  • AU: A
Routes of
administration		By mouth, rectal, intravascular, intramuscular
ATC code
Legal status
Legal status
  • AU: S2 (Pharmacy medicine)
  • CA: OTC
  • US: OTC
Pharmacokinetic data
MetabolismLiver
Elimination half-life5.5 hours[1] (diphenhydramine component)
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.007.593 Edit this at Wikidata
 ☒NcheckY (what is this?)  (verify)

Dimenhydrinate, also known as diphenhydramine/8-chlorotheophylline salt and sold under the brand name Dramamine, 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.[2]

Dimenhydrinate was introduced to the market by G.D. Searle in 1949.[3][4]

Medical uses

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Pills sold in Phonm Penh over the counter

Dimenhydrinate is an over-the-counter (OTC) first-generation antihistamine indicated for the prevention and relief of nausea and vomiting from a number of causes, including motion-sickness and post-operative nausea.[2]

Dimenhydrinate (Dramamine) can also be used for Insomnia, but this is an off label use. [5]

Side effects

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Common side effects of dimenhydrinate may include drowsiness, dry mouth, nose, or throat, constipation, and blurred vision. Some individuals, particularly children, may experience feelings of restlessness or excitement. In certain cases, more severe symptoms may arise, such as delirium, weakness, and a tendency to be easily startled. Hallucinations, psychosis, and an unusual sensitivity to sudden sounds have also been reported.[6][7][8] Continuous and/or cumulative use of anticholinergic medications, including first-generation antihistamines, is associated with higher risk of cognitive decline and dementia in older people. However, in younger people this is not relevant. [9][10]

Pharmacology

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Pharmacodynamics

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Diphenhydramine is the primary constituent of dimen­hydrinate and dictates the primary effect. The main differences relative to pure diphen­hydramine are a lower potency due to being combined with 8-chloro­theo­phylline (by weight, dimen­hydrinate is between 53% and 55.5% diphen­hydramine)[11] and the fact that the stimulant properties of 8-chloro­theo­phylline help reduce the side effect of drowsiness brought on by diphen­hydramine. Diphen­hydramine is itself an H1 receptor antagonist that demonstrates anticholinergic activity.[12]

Pharmacokinetics

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The diphenhydramine component requires about 2 hours to reach peak concentration after either oral or sublingual administration of diphen­hydrinate, and has a half-life of 5 – 6 hours in healthy adults.[1]

Recreational use

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Dimenhydrinate is recreationally used as a deliriant.[13][14][15] Slang terms for Dramamine used this way include "drama", "dime", "dime tabs", "D-Q", "substance D", "d-house", and "drams".[16] 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.[17]

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.[14]

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.[18] 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.[19]

History

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Dimenhydrinate (then known as Compound 1694) was being tested as a potential treatment for hay fever and hives at Johns Hopkins Hospital in 1947 by allergists Dr. Leslie Gay and Dr. Paul Carliner. Among those who received the drug was a pregnant woman who had suffered from motion sickness her entire life. She remained symptom-free if she took dimenhydrinate a few minutes before boarding a trolley, whereas the placebo was ineffective. To confirm these findings, the following year, G.D. Searle & Co. conducted a trial in which dimenhydrinate or placebo was given to U.S. troops crossing the Atlantic during "a rough passage" in a converted freight ship, the General Ballou, for 10 days as a rescue therapy for sea sickness. The findings were positive, as were the findings of a second trial of mostly women on the ship's return voyage. Gay and Carliner announced their discovery at a meeting of the Johns Hopkins Medical Society on February 14, 1949, as well as in the Bulletin of The Johns Hopkins Hospital. The New York Times, the Baltimore Sun, and other national newspapers covered the discovery, and Dramamine was made available in drugstores later that year.[3][4][20]

Brand names

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Dimenhydrinate is marketed under many brand names: in the U.S., Mexico, Turkey and Thailand as Dramamine; in Serbia as Dimigal; 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 as Travacalm; in 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;[21] in Portugal as Viabom, Vomidrine, and Enjomin; in Spain as Biodramina; in Israel as Travamin; and in Pakistan as Gravinate.[22]

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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.[23]

”The Ending Of Dramamine” is the opening track of the album How To Leave Town by Car Seat Headrest.

References

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  1. ^ a b Scavone JM, Luna BG, Harmatz JS, von Moltke L, Greenblatt DJ (April 1990). "Diphenhydramine kinetics following intravenous, oral, and sublingual dimenhydrinate administration". Biopharmaceutics & Drug Disposition. 11 (3): 185–189. doi:10.1002/bdd.2510110302. PMID 2328304.
  2. ^ a b Zabirowicz ES, Gan TJ (2019). "34 - Pharmacology of Postoperative Nausea and Vomiting". In Hemmings Jr HC, Talmage ED (eds.). Pharmacology and Physiology for Anesthesia (Second ed.). Elsevier Inc. pp. 671–692. doi:10.1016/B978-0-323-48110-6.00034-X. ISBN 978-0-323-48110-6. S2CID 81387334.
  3. ^ a b Newman A (21 June 2012). "New Dramamine Ads Take Aim at Summer Vacationers". The New York Times. Retrieved 26 June 2023.
  4. ^ a b Grauer N (12 February 2019). "Hopkins History Moments: Neil A. Grauer explains how Hopkins expertise helped prevent seasickness". Johns Hopkins Medicine. Retrieved 27 June 2023.
  5. ^ "Dimenhydrinate for Insomnia Reviews".
  6. ^ "Dimenhydrinate". Drugs.com. Archived from the original on 28 May 2004. Retrieved 28 May 2004.
  7. ^ Fabiano N, Dholakia S, Walker LA, Smith AL (March 2024). "Chronic high-dose dimenhydrinate use contributing to early multifactorial cognitive impairment". BMJ Case Reports. 17 (3): e258493. doi:10.1136/bcr-2023-258493. PMC 10921430. PMID 38453220.
  8. ^ "Dimenhydrinate Oral: Uses, Side Effects, Interactions, Pictures, Warnings & Dosing - WebMD".
  9. ^ Gray SL, Anderson ML, Dublin S, Hanlon JT, Hubbard R, Walker R, et al. (March 2015). "Cumulative use of strong anticholinergics and incident dementia: a prospective cohort study". JAMA Internal Medicine. 175 (3): 401–407. doi:10.1001/jamainternmed.2014.7663. PMC 4358759. PMID 25621434.
  10. ^ Carrière I, Fourrier-Reglat A, Dartigues JF, Rouaud O, Pasquier F, Ritchie K, Ancelin ML (July 2009). "Drugs with anticholinergic properties, cognitive decline, and dementia in an elderly general population: the 3-city study". Archives of Internal Medicine. 169 (14): 1317–1324. doi:10.1001/archinternmed.2009.229. PMC 2933398. PMID 19636034.
  11. ^ "Dimenhydrinate injection, solution". Daily Med. U.S. National Library of Medicine. Archived from the original on 13 October 2014. Retrieved 19 July 2014.}}
  12. ^ 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.
  13. ^ "The Health Risks of Abusing Motion sickness pills". Narconon International. Retrieved 13 September 2016.
  14. ^ 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.
  15. ^ Gardner DM, Kutcher S (March 1993). "Dimenhydrinate abuse among adolescents". Canadian Journal of Psychiatry. 38 (2): 113–116. doi:10.1177/070674379303800208. PMID 8467436. S2CID 30190588.
  16. ^ Trix, Victoria (6 October 2009). "The Dangers of Dimenhydrinate Abuse". Bright Hub. Retrieved 13 September 2016.
  17. ^ "Dramamine". Budderbongs forums. Retrieved 13 September 2016.
  18. ^ "Are Teens Abusing Motion Sickness Pills? - Muir Wood Adolescent and Family Services". Archived from the original on 18 September 2016. Retrieved 13 September 2016.
  19. ^ Scharman EJ, Erdman AR, Wax PM, Chyka PA, Caravati EM, Nelson LS, et al. (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.
  20. ^ Sanger GJ, Andrews P (2018). "A History of Drug Discovery for Treatment of Nausea and Vomiting and the Implications for Future Research". Frontiers in Pharmacology. 9: 913. doi:10.3389/fphar.2018.00913. PMC 6131675. PMID 30233361.
  21. ^ "Aviomarin, tabletki, 50 mg, 5 szt". Dox.pl (in Polish).
  22. ^ "Gravinate [Dimenhydrinate]". Karachi Pakistan: The Searle Company. Archived from the original on 5 May 2013.
  23. ^ "Modest Mouse: 'This is a long drive...'". Portland: Glacial Pace Recordings. Archived from the original on 27 March 2019. Retrieved 26 March 2019.
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