| Identification | More | [Name]
Dimenhydrinate | [CAS]
523-87-5 | [Synonyms]
2-(benzhydryloxy)-n,n-dimethylethylamine 8-chlorotheophyllinate
8-chloro-3,7-dihydro-1,3-dimethyl-1h-purine-2,6-dione compound with 2-(diphenylmethoxy)-n,n-dimethylethanamine (1:1)
DIMENHYDRINATE
DRAMAMINE
N-[2-DIPHENYLMETHOXYETHYL]-N,N-DIMETHYLAMMONIUM 8-CHLORO-THEOPHYLLINATE
THEOHYDRAMINE
2-(benzhydryloxy)-n,n-dimethylethylaminecompd.with8-chlorotheophylline
2-(diphenylmethoxy)-n,n-dimethylethylamine8-chlorotheophyllinate
6-dione,8-chloro-3,7-dihydro-1,3-dimethyl-1h-purine-compd.with2-(dipheny
6-dione,8-chloro-3,7-dihydro-1,3-dimethyl-1h-pyrine-compdwith2-(diphenyl
8-chlorotheophylline,compd.with2-(diphenylmethoxy)-n,n-dimethylethylamine
amosyt
anautine
andramine
antemin
aviomarin
benzhydryl-beta-dimethylaminoethylether8-chlorotheophylline
beta-dimethylaminoethylbenzhydrylether1,3-dimethyl-8-chloroxanthine
chloranautine
diamarin | [EINECS(EC#)]
208-350-8 | [Molecular Formula]
C24H26ClN5O5 | [MDL Number]
MFCD00054265 | [Molecular Weight]
499.95 | [MOL File]
523-87-5.mol |
| Chemical Properties | Back Directory | [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). | [form ]
neat | [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 Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R61:May cause harm to the unborn child.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S53:Avoid exposure-obtain special instruction before use . | [WGK Germany ]
3
| [RTECS ]
XH5082000
| [TSCA ]
Yes | [HS Code ]
2939590000 | [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. | [Hazardous Substances Data]
523-87-5(Hazardous Substances Data) |
| Hazard Information | Back Directory | [General Description]
Crystalline white powder. | [Air & Water Reactions]
Slightly soluble in water. Slightly acidic. | [Health Hazard]
SYMPTOMS: Symptoms associated with this compound 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 this compound are not available but DIMENHYDRINATE is probably non-flammable. | [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 | [Originator]
Dramamine,Searle,US,1949 | [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 | [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. |
| Questions And Answer | Back Directory | [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.
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