Buy Dimenhydrinate (diphenhydramine) Cas 523-87-5

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.^[3]

Dimenhydrinate was introduced to the market by G.D. Searle in 1949.^[4]^[5]

Medical uses

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.^[3]

Side effects

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

Pharmacodynamics

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

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

Recreational use

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 number of Dramamine tablets generally necessary for a recreational dose. ^[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. Toxicity 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.

impurity Standards
Synonyms:NA
Chemical Name:Diphenhydramine [2-(diphenylmethoxy)-N,N-dimethylethanamine] 8-chlorotheophylline (8-chloro-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione) (as per EP)

Technical Parameters

Basic Identity

Product Name	Dimenhydrinate
CAS	523-87-5
Synonyms	Apo Dimenhydrinate, Apo-Dimenhydrinate, Aviomarin, Biodramina, Calm X, Calm-X, Cinfamar, Contramareo, Dimen Heumann, Dimen Lichtenstein, Dimenhydrinate, Dimetabs, Dinate, Diphenhydramine Theoclate, DMH, Dramamine, Dramanate, Gravol, Heumann, Dimen, Lünopharm, Reisetabletten, Lichtenstein, Dimen, Marmine, Motion Aid, Motion-Aid, Nausicalm, Reisegold, Reisetabletten Lünopharm, Reisetabletten ratiopharm, Reisetabletten Stada, Reisetabletten-ratiopharm, Rodovan, RubieMen, Stada, Reisetabletten, Superpep, Theoclate, Diphenhydramine, Travel Well, TripTone, Vertigo Vomex, Vertigo-Vomex, Vomacur, Vomex A, Vomisin, Wehamine
Molecular Formula	C17H21NO.C7H7ClN4O2 C24H28ClN5O3
Molecular Weight	470.0 g/mol

Structural Identifiers

SMILES	CN1C2=C(C(=O)N(C1=O)C)NC(=N2)Cl.CN(C)CCOC(C1=CC=CC=C1)C2=CC=CC=C2
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)
InChIKey	NFLLKCVHYJRNRH-UHFFFAOYSA-N

Commercial & Availability

Standard Pack Sizes	100 mg / 200 mg / 1 g / 5 g / Bulk Custom
Availability	In Stock
Custom Synthesis	Available on request

Handling Information

Appearance	Solid powder
Solubility	Slightly soluble (1-10 mg/ml at 72 °F) (NTP, 1992) FREELY SOL IN ALCOHOL, CHLOROFORM; SOL IN BENZENE; SOL IN WATER: ABOUT 3 MG/ML; ALMOST INSOL IN ETHER
Storage	Dry, dark and at 0 – 4 C for short term (days to weeks) or -20 C for long term (months to years).

Dimenhydrinate Chemical Profile and Pharmacology

Dimenhydrinate (CAS 523-87-5) is a first-generation ethanolamine-derivative H1 receptor antagonist, formulated as a theoclate salt combining diphenhydramine (53%-55.5%) and 8-chlorotheophylline (44%-47%) [1]. It is primarily indicated for the prevention and treatment of motion sickness, vertigo, and associated nausea/vomiting [2]. Dimenhydrinate acts as a competitive antagonist at histamine H1 receptors in the vestibular system [3], with the antiemetic effect attributed to diphenhydramine, while 8-chlorotheophylline provides mild CNS stimulation via adenosine receptor blockade [4].

+H1 receptor antagonist for vestibular and emesis research models

+Theoclate salt combining diphenhydramine and 8-chlorotheophylline

+Adenosine receptor blockade component for CNS stimulation studies

Why Dimenhydrinate Cannot Be Replaced by Other Antihistamines

Dimenhydrinate’s clinical and physicochemical differentiation from its closest analogs—diphenhydramine, meclizine, cyclizine, and promethazine—prevents straightforward substitution. Differences in active moiety content (50 mg dimenhydrinate contains only 27.2-29 mg diphenhydramine), delayed onset kinetics due to salt dissociation, altered sedation profiles via the 8-chlorotheophylline counterion, and distinct vestibular suppression characteristics all preclude interchangeability without protocol revalidation [1][2][3].

⚠ Active moiety potency: 50 mg dimenhydrinate provides only ~27–29 mg diphenhydramine, requiring dose recalculation for equipotent replacement.

⚠ Salt dissociation delays onset kinetics vs. free diphenhydramine HCl, which may shift acute response endpoints.

⚠ 8-chlorotheophylline counterion adds adenosine receptor blockade, altering sedation profile compared to antihistamines lacking this component.

Comparative Evidence: Dimenhydrinate vs. Analogs

Diphenhydramine: Dose Potency and Delayed Onset

Dimenhydrinate demonstrates approximately 50% lower potency on a weight-for-weight basis compared to diphenhydramine hydrochloride [1]. A standard 50 mg oral dose of dimenhydrinate contains only 27.2-29 mg of active diphenhydramine, and requires in vivo dissociation into its constituents before exerting pharmacological effect, resulting in a delayed onset of action relative to direct diphenhydramine administration [2][3].

Diphenhydramine potency

Head-to-head

50 mg dimenhydrinate contains 27.2–29 mg diphenhydramine; onset 15–30 min vs immediate HCl

Dose adjustment context for direct substitution

May result in underdosing if dose not corrected

PharmacokineticsMotion SicknessAntihistamine

Meclizine: VOR Gain Suppression in Space Motion Sickness

In a double-blind, placebo-controlled study of space motion sickness countermeasures, dimenhydrinate (40 mg) combined with cinnarizine (25 mg) reduced vestibulo-ocular reflex (VOR) gain from 0.54 ± 0.05 to 0.45 ± 0.05 [1]. Meclizine (25 mg) similarly reduced VOR gain from 0.54 ± 0.05 to 0.38 ± 0.06. Both agents significantly decreased semicircular canal-mediated vestibular output.

VOR gain suppression

Cross-study comparable

Dimenhydrinate+cinnarizine: ΔVOR = -0.09; Meclizine: ΔVOR = -0.16

Calibrated vestibular suppression endpoint context

Electronystagmography; reported baseline 0.54±0.05

Vestibular PharmacologySpace Motion SicknessVOR

Scopolamine: Comparable Motion Sickness Efficacy

A Cochrane review of 14 RCTs (n=1,025) reported that scopolamine reduced nausea relative to placebo (RRR=0.47; 95% CI, 0.31-0.71) [1]. Among the three RCTs directly comparing scopolamine with antihistamines, one study found scopolamine equivalent to dimenhydrinate in efficacy [1].

Scopolamine efficacy

Head-to-head

Equivalent efficacy in one RCT; scopolamine RRR 0.47 (95% CI 0.31–0.71) vs placebo

Reported comparator endpoint context

Single RCT; broader scopolamine efficacy established

Motion SicknessAntihistamineAnticholinergic

Promethazine: Psychomotor Performance Impairment

In a double-blind crossover study of 21 subjects assessing aircrew psychomotor performance, dimenhydrinate 50 mg impaired performance on the Simple Reaction Time (SRT) task only, whereas promethazine 25 mg plus d-amphetamine 10 mg did not impair performance on any task nor increase sleepiness [1][2].

Psychomotor performance

Head-to-head

Dimenhydrinate 50 mg impaired SRT only; promethazine+amphetamine: no impairment

Task-specific impairment profile context

Aircrew performance model; 8 h post-dose

Psychomotor PerformanceAviation MedicineAntihistamine

Cyclizine and Meclizine: Sedation Profile Comparison

Class-level evidence indicates that dimenhydrinate is more sedating than cyclizine and meclizine [1]. Moderate motion sickness conditions may be controlled by dimenhydrinate 50 mg, while mild conditions may be adequately managed with cyclizine 50 mg or meclizine 50 mg [1]. This stratification is based on the relative CNS depressant properties of each agent.

Sedation ranking

Class-level

More sedating than cyclizine and meclizine (qualitative ranking)

Sedation intensity context for motion models

Based on clinical practice guidelines

Motion SicknessSedationAntihistamine

β-Cyclodextrin Complexation for Enhanced Solubility

Dimenhydrinate exhibits poor aqueous solubility, but complexation with β-cyclodextrin (β-CD) significantly improves its dissolution profile [1]. Molecular docking revealed a binding affinity of -4.2 kcal/mol between β-CD and diphenhydramine [1]. Fast-disintegrating tablet (FDT) formulations containing 9% crospovidone achieved optimal disintegration time [1].

β-Cyclodextrin complexation

Supporting evidence

Binding affinity -4.2 kcal/mol; 9% crospovidone FDT optimal disintegration

Formulation-dissolution enhancement context

In vitro complexation; FDT formulation data

Buy Dimenhydrinate (diphenhydramine) Cas 523-87-5

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- CAS: 523-87-5
- Molecular Weight: 470.0 g/mol
- Molecular Formula: C17H21NO.C7H7ClN4O2C24H28ClN5O3
- Product Name: Dimenhydrinate
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