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 Ethanolamine (2-aminoethanol, monoethanolamine, ETA, or MEA) is an organic chemical compound with the formula or . The molecule is bifunctional, containing both a primary amine and a primary alcohol. Ethanolamine is a colorless, viscous liquid wit ...

derivative, and 8-chlorotheophylline, a chlorinated theophylline derivative, in a 1:1 ratio.

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 The H1 receptor is a histamine receptor belonging to the family of rhodopsin-like G-protein-coupled receptors. This receptor is activated by the biogenic amine histamine. It is expressed in smooth muscles, on vascular endothelial cells, in the h ...

antagonist An antagonist is a character in a story who is presented as the chief foe of the protagonist. Etymology The English word antagonist comes from the Greek ἀνταγωνιστής – ''antagonistēs'', "opponent, competitor, villain, enemy, riv ...

that demonstrates anticholinergic activity.

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 Potency may refer to: * Potency (pharmacology), a measure of the activity of a drug in a biological system * Virility * Cell potency, a measure of the differentiation potential of stem cells * In homeopathic dilutions, potency is a measure of how ...

due to being combined with 8-chlorotheophylline. By weight, dimenhydrinate is between 53% to 55.5% diphenhydramine.

Side effects

Common side effects may include: *Drowsiness *Dry mouth, nose, or throat *Constipation *Blurred vision *Feeling restless or excited (especially in children) 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.

Recreational use

Dimenhydrinate is recreationally used as a deliriant. Slang terms for Dramamine used this way include "drama", "dime", "dime tabs", "D-Q", "substance D", "d-house", and "drams". 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. Many users report a side-effect profile consistent with tropane alkaloid (e.g.

atropine Atropine is a tropane alkaloid and anticholinergic medication used to treat certain types of nerve agent and pesticide poisonings as well as some types of slow heart rate, and to decrease saliva production during surgery. It is typically given i ...

) poisoning as both show antagonism of muscarinic acetylcholine receptors in both the central and autonomic nervous system, which inhibits various signal transduction pathways. Other CNS effects occur within the

limbic system The limbic system, also known as the paleomammalian cortex, is a set of brain structures located on both sides of the thalamus, immediately beneath the medial temporal lobe of the cerebrum primarily in the forebrain.Schacter, Daniel L. 2012. ''Ps ...

and hippocampus, causing confusion and temporary

amnesia Amnesia is a deficit in memory caused by brain damage or disease,Gazzaniga, M., Ivry, R., & Mangun, G. (2009) Cognitive Neuroscience: The biology of the mind. New York: W.W. Norton & Company. but it can also be caused temporarily by the use ...

due to decreased

acetylcholine Acetylcholine (ACh) is an organic chemical that functions in the brain and body of many types of animals (including humans) as a neurotransmitter. Its name is derived from its chemical structure: it is an ester of acetic acid and choline. Part ...

signaling. Toxicology also manifests in the autonomic nervous system, primarily at the

neuromuscular junction A neuromuscular junction (or myoneural junction) is a chemical synapse between a motor neuron and a muscle fiber. It allows the motor neuron to transmit a signal to the muscle fiber, causing muscle contraction. Muscles require innervation to ...

, 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 Arrhythmias, also known as cardiac arrhythmias, heart arrhythmias, or dysrhythmias, are irregularities in the heartbeat, including when it is too fast or too slow. A resting heart rate that is too fast – above 100 beats per minute in adults ...

, coma, and death. Such a side effect profile is thought to give

-class antihistamines a relatively low abuse liability. An antidote that can be used for dimenhydrinate poisoning is physostigmine.

Brand names

Dimenhydrinate is marketed under many brand names: in the U.S., Mexico, Turkey, Serbia, and Thailand 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; in Portugal as Viabom, Vomidrine, and Enjomin; in Spain as Biodramina; in Israel as Travamin; in Pakistan as Gravinate; and in Ethiopia as dimenhydrinate.

Popular culture

Modest Mouse Modest Mouse is an American rock band formed in 1992 in Issaquah, Washington, and currently based in Portland, Oregon. The founding members are lead singer/guitarist Isaac Brock, drummer Jeremiah Green, and bassist Eric Judy. Strongly influenced ...

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. In ''

Columbo ''Columbo'' () is an American crime drama television series starring Peter Falk as Lieutenant Columbo, a homicide detective with the Los Angeles Police Department. After two pilot episodes in 1968 and 1971, the show originally aired on NBC f ...

'' season 4 episode 4 "Troubled Waters", Columbo, suffering sea sickness, is given Dramamine by the nurse and later reports it "saved his life".

References

External links

* * * {{Portal bar , Medicine Combination drugs Muscarinic antagonists H1 receptor antagonists Deliriants Antiemetics Monoamine reuptake inhibitors Motion sickness