Dimenhydrinate Chemical Properties

Melting point:

102-107°C

Density 

1.2586 (rough estimate)

refractive index 

1.6500 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Slightly soluble in water, freely soluble in ethanol (96 per cent).

color 

White to Off-White

Water Solubility 

Slightly soluble (0.1-1 g/100 mL at 22 ºC)

Stability:

Hygroscopic

InChIKey

NFLLKCVHYJRNRH-UHFFFAOYSA-N

CAS DataBase Reference

523-87-5(CAS DataBase Reference)

EPA Substance Registry System

Dimenhydrinate (523-87-5)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-61-36/37/38

Safety Statements 

22-26-36/37/39-53

WGK Germany 

3

RTECS 

XH5082000

TSCA 

Yes

HS Code 

2939590000

Hazardous Substances Data

523-87-5(Hazardous Substances Data)

MSDS

• Language:English Provider:N-(2-Diphenylmethoxyethyl)-N,N-dimethylammonium 8-chlorotheophyllinate
• Language:English Provider:SigmaAldrich

Dimenhydrinate Usage And Synthesis

Anti-motion sickness

Dimenhydrinate is a complex salt of diphenhydramine and 8-chloro-theophylline. Antihistamine effect is weaker than diphenhydramine , and its anti-motion sickness and antiemetic effects are stronger. Mainly it is used to prevent and control nausea, vomiting, dizziness and Meniere's syndrome caused by motion sickness, .It is effective to treat a variety of dizziness, vomiting caused by radiation therapy, pregnancy, surgery, inner ear infections, and the use of drugs (such as streptomycin) .

Traits

Dimenhydrinate is transparent white crystalline powder, odorless, slightly soluble in water, soluble in ethanol.

Effect

As a complex salt of diphenhydramine and 8-chloro-theophylline,its role is the same as diphenhydramine hydrochloride, but its anti-histamine effect is weaker than the latter. It can inhibit medulla vomiting chemosensory area and it has a general central pivot inhibition effect and anticholinergic effects, which makes it have sedative and antiemetic effects.
It is quickly and completely absorbed after oral administration, it is effective after 15 to 60 minutes , the role is sustainable after 3-6 hours, the elimination phase half-life (t1/2β) is 4~6 hours, plasma protein binding rate is high. Mainly it is metabolized in the liver, it is excreted in urine in the form of metabolites . Patients with hepatic insufficiency using this service,because it can accumulate in the body , the dose should be reduced.
The above information is edited by the chemicalbook of Tian Ye.

Medicine interactions

1.It can not be taken with other CNS depressants and it cannot be taken after drinking.
2. It can be used to make ethanol, central nervous system depressants, tricyclic antidepressants more effective. It can momentarily affect barbiturates and sulfacetamide sodium absorption; if it is used with sodium aminosalicylate , plasma concentration of the latter is decreased.
3. Administration with food or milk can reduce the irritation of the stomach of the drug .

Precautions

1. The composition of the production and other ethanolamine allergies, newborns and premature infants are disabled.
2. It pregnant women in early pregnancy within four months use the drug, the incidence of congenital cardiovascular abnormalities and inguinal hernia of the fetus may be increased, the relationship with drug use has not been confirmed. Early pregnancy should not take this product.
3. The anti-emetic effect of the product can adds difficulty in diagnosing appendicitis and drug-induced reactions.
4. Lethargy , inability to concentrate etc.,can occur after treatment, ,patients should not drive cars, boats, etc., and it is not suitable to engage in the highly difficult and dangerous machine operation.

Adverse reactions

Low toxicity, high doses can cause drowsiness, and even cause a rash. Long-term use may cause blood diseases.

Uses

It is suitable for motion-sickness, pregnancy, radiation therapy , surgery etc. induced nausea , vomiting and dizziness.

Description

Dimenhydrinate (16.1.2) is a complex compound of N, N-dimethyl (2- diphenylmethoxy)ethylamine—diphenhydramine with 8-chlorotheophylline. While blocking the H1 receptor, dimenhydrinate simultaneously acts on the vomiting center.

Chemical Properties

White Solid
Dimenhydrinate is freely soluble in ethanol and chloroform, slightly soluble in water, and almost in-soluble in ether.

Originator

Dramamine,Searle,US,1949

Uses

Dimenhydrinate is used for preventing and stopping sea or airsickness, and for nausea and vomiting. Synonyms of this drug are dramamine, dadalon, emedyl, travelin, and others.

Uses

An antihistamine with antiemetic properties used to prevent nausea and motion sicknes composed of two drugs 8-Chlorotheophylline (C411440) and Diphenhydramine (D486900).

Uses

Used for treating vertigo, motion sickness, and nausea associated with pregnancy

Definition

ChEBI: The diphenhydramine salt of 8-chlorotheophylline. Its effects are similar to those of diphenhydramine, but it is less potent. It was thought that by combining the antiemetic effects of diphenhydramine with the mild stimulant effects of 8-chlorotheophyline, the extreme drowsiness induced by the former would be mitigated. However, the sedation caused by diphenhydramine is considerably stronger than the stimulation caused by 8-chlorotheophylline. Dimenhydrinate is used mainly as an antiemetic in the prevention nd treatment of motion sickness.

Manufacturing Process

58.8 grams of 8-chlorotheophylline and 70 grams of β-dimethylaminoethyl benzohydryl ether are dissolved in 150 cc of hot methanol. Then 5 grams of activated charcoal are added and the mixture is boiled for an hour. It is filtered hot and the filtrate cooled. The crystalline precipitate of βdimethylaminoethyl benzohydryl ether 8-chlorotheophyllinate is collected on a filter, washed with ether and dried. It melts at 96-99°C. It is dissolved in boiling ethyl acetate, filtered hot to remove any insoluble material, and then chilled. The salt so obtained melts at 102.5°-104°C after filtration, washing with ether and drying.

brand name

Dommanate (Forest).

Therapeutic Function

Antinauseant

General Description

The 8-chlorotheophyllinate (theoclate) salt of diphenhydramine, 8-chlorotheophylline 2-(diphenylmethoxy)-N,N-dimethylethylamine (Dramamine), is a white crystalline, odorless powder that is highly soluble in water and freely soluble in alcohol and chloroform. Dimenhydrinate is recommended for nausea of motion sickness and for hyperemesis gravidarum (nausea of pregnancy).

General Description

Crystalline white powder.

Air & Water Reactions

Slightly soluble in water. Slightly acidic.

Health Hazard

SYMPTOMS: Symptoms associated with Dimenhydrinate include: drowsiness, lethargy, fatigue hypnosis and coma. Initial sedation may be followed by central nervous system hyperexcitability. Also, the victim may experience dry mouth, anorexia, nausea, vomiting, abdominal distress, constipation, and/or diarrhea.

Fire Hazard

Flash point data for Dimenhydrinate are not available but Dimenhydrinate is probably non-flammable.

Safety Profile

Poison by intraperitoneal and intravenous routes. Moderately toxic by ingestion. A drug much used for motion sickness. Human systemic effects by ingestion: arrhythmias, convulsions, distorted perceptions, hallucinations, intracranial pressure increase. Mutation data reported. When heated to decomposition it emits very toxic fumes of NOx, and Cl-. See also AMINES.

Veterinary Drugs and Treatments

In veterinary medicine, dimenhydrinate is used primarily for its antiemetic effects for vomiting and in the prophylactic treatment of motion sickness in dogs and cats. Dimenhydrinate may be useful as an adjunctive treatment for feline pancreatitis. As dimenhydrinate is often thought of as “half-strength diphenhydramine” it can be employed whenever a histmine-1 blocker is desired.

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