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Dimenhydrinate

Combination of
diphenhydramine	antihistamine
8-chlorotheophylline	stimulant
Clinical data
AHFS/Drugs.com	Monograph
MedlinePlus	a607046
Pregnancy category	AU: A
Routes of administration	Oral, Rectal, I.V.
ATC code	R06AA02
Legal status
Legal status	AU: S2 (Pharmacy medicine) US: OTC
Identifiers
CAS Number	523-87-5
PubChem CID	10660
DrugBank	DB00985
ChemSpider	10210
UNII	JB937PER5C
KEGG	D00520
CompTox Dashboard (EPA)	DTXSID9025087
ECHA InfoCard	100.007.593
Chemical and physical data
3D model (JSmol)	Interactive image
SMILES O=C2N(c1nc(Cl)nc1C(=O)N2C)C.O(CCN(C)C)C(c1ccccc1)c2ccccc2
InChI InChI=1S/C17H21NO.C7H7ClN4O2/c1-18(2)13-14-19-17(15-9-5-3-6-10-15)16-11-7-4-8-12-16;1-11-4-3(9-6(8)10-4)5(13)12(2)7(11)14/h3-12,17H,13-14H2,1-2H3;1-2H3,(H,9,10) Key:NFLLKCVHYJRNRH-UHFFFAOYSA-N
(what is this?)  (verify)

Dimenhydrinate (in US marketed under brand names Dramamine, Driminate, Gravol, Gravamin, Vomex, and Vertirosan) is an over-the-counter drug used to prevent nausea and motion sickness. It is marketed in Canada as Gravol, in Portugal as Viabom, in Brazil as Dramin, in Ecuador as Anautin, in Hungary as Daedalon, and in Indonesia under the brand name Antimo, and in Thailand, Dimenhydrinate (ไดเมนไฮดริเนท), is marketed under the brand name ไดเมนนีน. It is most commonly used as pills, although it is also available in liquid form and in suppositories. Chemically, dimenhydrinate is a salt of two drugs: diphenhydramine, and 8-chlorotheophylline, a chlorinated derivative of theophylline.

Dimenhydrinate "has been reported to be abused for non-medicinal purposes. Street drug users abuse DMH for the acute effects of euphoric sensations and hallucinations, while psychiatric patients abuse DMH for its anxiolytic or anti-cholinergic effects...Further support comes from reports of acute and chronic abuse of DMH by humans. Collectively, results confirm the abuse liability of DMH.

Effects

The effects of dimenhydrinate are very similar to those of diphenhydramine. The main differences are a lower potency, and a longer latency. 50 mg dimenhydrinate contains 27.2 mg of diphenhydramine, so it is less potent at equal doses. Also, dimenhydrinate must dissociate into diphenhydramine and its counterion in the body before it is active, so it produces effects more slowly than diphenhydramine. The drug typically takes a minimum of 4 hours to fully take effect.

Theophylline was added in order to counteract drowsiness. Theophylline is very closely related to caffeine and theobromine, mild central nervous system stimulants. It was thought that by combining the antiemetic effects of diphenhydramine with a stimulant, the extreme drowsiness induced by the former could be mitigated somewhat by the latter. The sedation caused by diphenhydramine, however, is substantially stronger than the stimulation caused by chlorotheophyllinate, so the overall effect is still mostly sedating. Diphenhydramine, an ethanolamine-class antihistamine, is found in most OTC sleep aids and allergy preparations, such as Tylenol PM and Benadryl. It is primarily a H₁-antagonist, but also possesses an antimuscarinic effect. It is used in Dramamine to prevent nausea and emesis; however, the development of the chemical meclizine has overtaken its usage (marketed as "Dramamine II") because meclizine is less likely to cause drowsiness.

Recreational use

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Dimenhydrinate is used as a deliriant at doses of 1200 to 2000 mg, although body weight plays a significant part in dosing of this drug. Slang terms for Dramamine used this way include "dime," "dime tabs," "D-Q," "substance D," "d-house," and "drams." Frequent users of Dramamine are sometimes called Dramatists, a pun on the name. Tripping on Dramamine is sometimes referred to as Dramatizing or "going a dime a dozen," a reference to the amount of Dramamine tabs generally necessary for a trip. The LD₅₀ (the dose at which 50% of animals tested produced fatal symptoms) for dimenhydrinate is 500 mg/kg in lab rats, which may suggest that a human of typical weight would need to ingest a greater than tenfold amount of a psychoactive dose in order to risk death: However it is important to note that LD₅₀ varies greatly even between mammals and is almost always lower for humans than for rats. As well, it is possible that a significant proportion may experience serious or fatal reactions at doses far lower than the LD₅₀.

Many users report a side effect profile consistent with tropane glycoalkaloidal (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. In the CNS, dimenhydrinate readily crosses the blood-brain barrier, exerting effects within the visual and auditory cortex.

The auditory/visual hallucinations coupled with the ensuing confusion and short-term memory loss often leads to mild or intense paranoia among the users. Though auditory hallucinations are more common than visual hallucinations, the visuals of a "Dramamine Trip" can seem very real. At higher doses the hallucinations are more frequent, realistic and in some cases, frightening. Taking Dramamine at higher doses is neither advised nor recommended -- potential for overdose is a risk. Hallucinations induced by Dramamine abuse are sometimes shared among users; that is, it is common for Dramamine users to hear their own name being called, to see frightening creatures (such as insects or zombies), and to have conversations with non-existent people. When taken before going to sleep, users tend to sit up and look around at their surroundings at random, sometimes within 2-5 minute intervals.

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 dysrhythmias, coma and death. Such a side-effect profile is thought to give ethanolamine-class antihistamines a relatively low abuse liability. The specific antidote for dimenhydrinate poisoning is physostigmine, usually given by IV in a hospital.

Veterinary use

Dimenhydrinate has successfully been used as an antiemetic and sedative in housepets. It is commonly used to reduce the effects of idiopathic vestibular syndrome. The suggested dosage is 50 mg for dogs and 10 mg for cats; duration of effect is 8 hours.

This dosage though is not a proper measure for all pets and should be adjusted by weight. Always consult a veterinarian before giving your dog or cat Gravol.

See also

• Diphenhydramine
• Doxylamine

References

1. Halpert, Alison; Olmstead, Mary; and Richard Beninger. "Mechanisms and abuse liability of the anti-histamine dimenhydrinate." Neuroscience & Biobehavioral Reviews; Jan2002, Vol. 26 Issue 1, p61, 7p
2. 2-4 mg per pound

• Muscarinic antagonists
• H1 receptor antagonists
• Deliriants
• Antiemetics
• Combination drugs