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Substance Name: Dimenhydrinate [USP:INN:BAN:JAN]
RN: 523-87-5
UNII: JB937PER5C
InChIKey: NFLLKCVHYJRNRH-UHFFFAOYSA-N

Note

  • A drug combination that contains DIPHENHYDRAMINE and THEOPHYLLINE. It is used for treating vertigo, motion sickness, and nausea associated with pregnancy. It is not effective in the treatment of nausea associated with cancer chemotherapy.

Molecular Formula

  • C17-H21-N-O.C7-H7-Cl-N4-O2

Molecular Weight

  • 469.97
 

Classification Codes

  • Anti-Emetic
  • Antiemetics
  • Autonomic Agents
  • Central Nervous System Agents
  • Drug / Therapeutic Agent
  • Gastrointestinal Agents
  • Histamine Agents
  • Histamine Antagonists
  • Histamine H1 Antagonists
  • Human Data
  • Mutation Data
  • Neurotransmitter Agents
  • Peripheral Nervous System Agents
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Names and Synonyms

Name of Substance

  • Dimenhydrinate
  • Dimenhydrinate [USP:INN:BAN:JAN]

MeSH Heading

  • Dimenhydrinate

Synonyms

  • (o-Benzhydryl(dimethylamino)ethanol) 8-chlorotheophyllinate
  • 1H-Pyrine-2,6-dione, 8-chloro-3,7-dihydro-1,3-dimethyl-, compd. with 2-(diphenylmethoxy)-N,N-dimethylethanamine (1:1)
  • 2-(Benzhydryloxy)-N,N-dimethylethylamine 8-chlorotheophyllinate
  • 2-(Benzhydryloxy)-N,N-dimethylethylamine compd. with 8-chlorotheophylline
  • 2-(Diphenylmethoxy)-N,N-dimethylethylamine 8-chlorotheophyllinate
  • 8-Chlorotheophylline, compd. with 2-(diphenylmethoxy)-N,N-dimethylethylamine (1:1)
  • 8-Chlorotheophylline, compound with 2-(diphenylmethoxy)-N,N-dimethylethylamine (1:1)
  • Amosyt
  • Anautine
  • Andramine
  • Antemin
  • Aviomarin
  • Benzhydryl-beta-dimethylaminoethylether 8-chlorotheophylline
  • beta-Dimethylaminoethyl benzhydryl ether 1,3-dimethyl-8-chloroxanthine
  • CCRIS 4798
  • Chloranautine
  • Diamarin
  • Dimate
  • Dimenest
  • Dimenhidrinato
  • Dimenhidrinato [INN-Spanish]
  • Dimenhydrinate
  • Dimenhydrinatum
  • Dimenhydrinatum [INN-Latin]
  • Dimenidrinato
  • Dimenidrinato [DCIT]
  • Dimentabs
  • Diphenhydramine 8-chlorotheophyllinate
  • Diphenhydramine 8-chlorotheophylline
  • Diphenhydrinate
  • Dommanate
  • Dramalen
  • Dramamin
  • Dramamine
  • Dramarin
  • Dramilin
  • Dramyl
  • Dromyl
  • EINECS 208-350-8
  • Eldodram
  • Emedyl
  • Ethylamine 2-(diphenylmethoxy)-N,N-dimethyl-, compd with 8-chlorotheophylline (1:1)
  • Ethylamine, N,N-dimethyl-2-(diphenylmethoxy)-, compd. with 8-chlorotheophylline
  • Faston
  • Gravinol
  • Gravinol (antiemetic)
  • Gravol
  • HSDB 3064
  • Hydrinate
  • Lomarin
  • Menhydrinate
  • N,N-Dimethyl-2-diphenylmethoxyethylamine 8-chlorotheophyllinate
  • NCI-C60639
  • Neo-navigan
  • Novamin
  • Novamin (VAN)
  • Novamine
  • NSC 117855
  • O-Benzhydryldimethylaminoethanol 8-chlorotheophyllinate
  • Permital
  • Reidamine
  • Reise-engletten
  • Removine
  • Supremal
  • Teodramin
  • Theophylline, 8-chloro-, compd with 2-(diphenylmethoxy)-N,N-dimethyethylamine (1:1)
  • Travelin
  • Travelmin
  • Troversin
  • UNII-JB937PER5C
  • Vomex A
  • Xamamina

Systematic Names

  • 1H-Purine-2,6-dione, 8-chloro-3,7-dihydro-1,3-dimethyl-, compd. with 2-(diphenylmethoxy)-N,N-dimethylethanamine (1:1)
  • Dimenhydrinate
  • Ethanamine, 2-(diphenylmethoxy)-N,N-dimethyl-, compd. with 8-chloro-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dione (1:1)
  • Ethylamine, 2-(diphenylmethoxy)-N, N-dimethyl-, compd. with 8-chlorothiophylline (1:1)
  • Theophylline, 8-chloro-, compd. with 2-(diphenylmethoxy)-N,N-dimethylethylamine (1:1)

Registry Numbers

CAS Registry Number

  • 523-87-5

FDA UNII

  • JB937PER5C

Other Registry Number

  • 133294-22-1

System Generated Number

  • 0000523875

Molecular Formulas

Molecular Formula

  • C17-H21-N-O.C7-H7-Cl-N4-O2

Molecular Formula Fragments

  • C17-H21-N-O
  • C7-H7-Cl-N4-O2
  • COMPONENT

Structure Descriptors

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

Smiles

CN(C)CCOC(c1ccccc1)c2ccccc2.CN3C(=O)N(C)c4[nH]c(Cl)nc4C3=O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human TDLo oral 714ug/kg (0.714mg/kg) BEHAVIORAL: EXCITEMENT Allergy. Vol. 50(Suppl,
infant TDLo oral 114mg/kg (114mg/kg) BEHAVIORAL: COMA

CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Journal of Toxicology, Clinical Toxicology. Vol. 29, Pg. 527, 1991.
man TDLo oral 714ug/kg (0.714mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" Allergy. Vol. 55, Pg. 297, 2000.
man TDLo oral 11400ug/kg (11.4mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" American Journal of Psychiatry. Vol. 128, Pg. 1012, 1972.
mouse LD50 intraperitoneal 149mg/kg (149mg/kg)   Drugs in Japan Vol. 6, Pg. 346, 1982.
mouse LD50 intravenous 90mg/kg (90mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 9, Pg. 759, 1967.
mouse LD50 oral 203mg/kg (203mg/kg)   Drugs in Japan Vol. 6, Pg. 346, 1982.
mouse LD50 subcutaneous 400mg/kg (400mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 9, Pg. 759, 1967.
pigeon LD50 intramuscular > 200mg/kg (200mg/kg)   Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 46, Pg. 140, 1957.
rat LD50 intravenous 200mg/kg (200mg/kg)   Compilation of LD50 Values of New Drugs.
rat LD50 oral 1320mg/kg (1320mg/kg)   Drugs in Japan Vol. 6, Pg. 346, 1982.
women LDLo oral 100mg/kg (100mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BRAIN AND COVERINGS: INCREASED INTRACRANIAL PRESSURE

CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)		 Annals of Emergency Medicine. Vol. 22, Pg. 1481, 1993.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 204.5 deg C   EXP
log P (octanol-water) -0.390 (none)   EST
Water Solubility 3000 mg/L   EXP
Atmospheric OH Rate Constant 9.91E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.