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Chemistry

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Also known as: 523-87-5, Dramamine, Chloranautine, Vomex a, Diphenhydrinate, Anautine
Molecular Formula
C24H28ClN5O3
Molecular Weight
470.0  g/mol
InChI Key
NFLLKCVHYJRNRH-UHFFFAOYSA-N
FDA UNII
JB937PER5C

Dimenhydrinate
A drug combination that contains diphenhydramine and theophylline. It is used for treating VERTIGO, MOTION SICKNESS, and NAUSEA associated with PREGNANCY.
1 2D Structure

Dimenhydrinate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-benzhydryloxy-N,N-dimethylethanamine;8-chloro-1,3-dimethyl-7H-purine-2,6-dione
2.1.2 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)
2.1.3 InChI Key
NFLLKCVHYJRNRH-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CN1C2=C(C(=O)N(C1=O)C)NC(=N2)Cl.CN(C)CCOC(C1=CC=CC=C1)C2=CC=CC=C2
2.2 Other Identifiers
2.2.1 UNII
JB937PER5C
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Apo Dimenhydrinate

2. Apo-dimenhydrinate

3. Aviomarin

4. Biodramina

5. Calm X

6. Calm-x

7. Cinfamar

8. Contramareo

9. Dimen Heumann

10. Dimen Lichtenstein

11. Dimetabs

12. Dinate

13. Diphenhydramine Theoclate

14. Dmh

15. Dramamine

16. Dramanate

17. Gravol

18. Heumann, Dimen

19. Lnopharm, Reisetabletten

20. Lichtenstein, Dimen

21. Marmine

22. Motion Aid

23. Motion-aid

24. Nausicalm

25. Reisegold

26. Reisetabletten Lnopharm

27. Reisetabletten Ratiopharm

28. Reisetabletten Stada

29. Reisetabletten-ratiopharm

30. Rodovan

31. Rubiemen

32. Stada, Reisetabletten

33. Superpep

34. Theoclate, Diphenhydramine

35. Travel Well

36. Triptone

37. Vertigo Vomex

38. Vertigo-vomex

39. Vomacur

40. Vomex A

41. Vomisin

42. Wehamine

2.3.2 Depositor-Supplied Synonyms

1. 523-87-5

2. Dramamine

3. Chloranautine

4. Vomex A

5. Diphenhydrinate

6. Anautine

7. Travelin

8. Amosyt

9. Aviomarin

10. Gravol

11. Menhydrinate

12. Andramine

13. Antemin

14. Diamarin

15. Dimenest

16. Dimentabs

17. Dramalen

18. Dramamin

19. Dramarin

20. Dramilin

21. Eldodram

22. Gravinol

23. Hydrinate

24. Novamine

25. Permital

26. Supremal

27. Teodramin

28. Travelmin

29. Troversin

30. Xamamina

31. Dimate

32. Dramyl

33. Dromyl

34. Reise-engletten

35. Neo-navigan

36. Diphenhydramine Theoclate

37. Diphenhydramine 8-chlorotheophylline

38. Diphenhydramine 8-chlorotheophyllinate

39. Nsc 117855

40. Jb937per5c

41. O-benzhydryldimethylaminoethanol 8-chlorotheophyllinate

42. Nsc-117855

43. 1h-purine-2,6-dione, 8-chloro-3,7-dihydro-1,3-dimethyl-, Compd. With 2-(diphenylmethoxy)-n,n-dimethylethanamine (1:1)

44. 8-chloro-1,3-dimethyl-1h-purine-2,6(3h,7h)-dione Compound With 2-(benzhydryloxy)-n,n-dimethylethanamine (1:1)

45. (o-benzhydryl(dimethylamino)ethanol) 8-chlorotheophyllinate

46. Benzhydryl-beta-dimethylaminoethylether 8-chlorotheophylline

47. N,n-dimethyl-2-diphenylmethoxyethylamine 8-chlorotheophyllinate

48. 2-(diphenylmethoxy)-n,n-dimethylethylamine 8-chlorotheophyllinate

49. Beta-dimethylaminoethyl Benzhydryl Ether 1,3-dimethyl-8-chloroxanthine

50. 2-(benzhydryloxy)-n,n-dimethylethylamine Compd. With 8-chlorotheophylline

51. 8-chlorotheophylline, Compound With 2-(diphenylmethoxy)-n,n-dimethylethylamine (1:1)

52. Dimenhydrinat

53. Theohydramine

54. Dommanate

55. Lomarin

56. Reidamine

57. Removine

58. Emedyl

59. Faston

60. 2-benzhydryloxy-n,n-dimethylethanamine;8-chloro-1,3-dimethyl-7h-purine-2,6-dione

61. Novamin (van)

62. Gravinol (antiemetic)

63. Dimenidrinato [dcit]

64. Sr-05000001608

65. [o-benzhydryl(dimethylamino)ethanol] 8-chlorotheophyllinate

66. Dimenhydrinatum [inn-latin]

67. Dimenidrinato

68. Dimenhidrinato [inn-spanish]

69. Ccris 4798

70. Hsdb 3064

71. Dramamine (tn)

72. Nci-c60639

73. 2-(diphenylmethoxy)-n,n-dimethylethanamine And 8-chloro-1,3-dimethyl-3,9-dihydro-1h-purine-2,6-dione

74. Dimenhydrinate,(s)

75. Einecs 208-350-8

76. Mfcd00054265

77. Spectrum_000974

78. Prestwick3_000265

79. Spectrum2_000992

80. Spectrum3_000397

81. Spectrum4_000517

82. Spectrum5_000909

83. Dsstox_cid_5087

84. Unii-jb937per5c

85. Dimenhydrinate [mi]

86. Schembl5128

87. Dimenhydrinate [inn]

88. Dimenhydrinate [jan]

89. Dsstox_rid_77660

90. Dsstox_gsid_25087

91. Bspbio_000110

92. Bspbio_002213

93. Dimenhydrinate [hsdb]

94. Kbiogr_001093

95. Kbioss_001454

96. Dimenhydrinate [vandf]

97. Divk1c_000049

98. Spectrum1500251

99. Spbio_001083

100. Dimenhydrinate [mart.]

101. Bpbio1_000122

102. Dimenhydrinate [usp-rs]

103. Dimenhydrinate [who-dd]

104. Chembl1200406

105. Dtxsid9025087

106. Chebi:94848

107. Hms500c11

108. Kbio1_000049

109. Kbio2_001454

110. Kbio2_004022

111. Kbio2_006590

112. Kbio3_001433

113. Dimenhydrinate (jp17/usp/inn)

114. Ninds_000049

115. Hms1920g20

116. Hms2091o08

117. Hms2095f12

118. Hms3712f12

119. Pharmakon1600-01500251

120. 2-(benzhydryloxy)-n,n-dimethylethylamine 8-chlorotheophyllinate

121. Hy-b1215

122. Dimenhydrinate [ep Impurity]

123. Dimenhydrinate [orange Book]

124. Dimenhydrinate [usp:inn:ban:jan]

125. Tox21_200323

126. Ccg-40210

127. Dimenhydrinate [ep Monograph]

128. Nsc117855

129. Nsc756740

130. S4672

131. Dimenhydrinate [usp Monograph]

132. Dimenhydrinate For Peak Identification

133. Akos015896341

134. Ac-8241

135. Cs-4841

136. Db00985

137. Nsc-756740

138. 8-chlorotheophylline, Compd. With 2-(diphenylmethoxy)-n,n-dimethylethylamine (1:1)

139. Ethylamine 2-(diphenylmethoxy)-n,n-dimethyl-, Compd With 8-chlorotheophylline (1:1)

140. Ethylamine, 2-(diphenylmethoxy)-n, N-dimethyl-, Compd. With 8-chlorothiophylline (1:1)

141. Ethylamine, N,n-dimethyl-2-(diphenylmethoxy)-, Compd. With 8-chlorotheophylline

142. Idi1_000049

143. Theophylline, 8-chloro-, Compd With 2-(diphenylmethoxy)-n,n-dimethyethylamine (1:1)

144. Theophylline, 8-chloro-, Compd. With 2-(diphenylmethoxy)-n,n-dimethylethylamine (1:1)

145. Ncgc00021154-01

146. Ncgc00021154-02

147. Ncgc00021154-03

148. Ncgc00021154-04

149. Ncgc00021154-05

150. Ncgc00021154-06

151. Ncgc00021154-07

152. Ncgc00091928-01

153. Ncgc00091928-02

154. Ncgc00091928-03

155. Ncgc00257877-01

156. 1h-pyrine-2,6-dione, 8-chloro-3,7-dihydro-1,3-dimethyl-, Compd. With 2-(diphenylmethoxy)-n,n-dimethylethanamine (1:1)

157. As-13166

158. Bd166163

159. Ethanamine, 2-(diphenylmethoxy)-n,n-dimethyl-, Compd. With 8-chloro-3,7-dihydro-1,3-dimethyl-1h-purine-2,6-dione (1:1)

160. Sbi-0051350.p003

161. Ab00053833

162. Ft-0625019

163. Ft-0696921

164. D00520

165. D82297

166. Wln: T56 Bm Dn Fnvnvj Cg F H &622

167. 523d875

168. Q420439

169. Sr-05000001608-1

170. Sr-05000001608-2

171. Brd-m98649031-001-01-1

172. Dimenhydrinate, European Pharmacopoeia (ep) Reference Standard

173. Dimenhydrinate, United States Pharmacopeia (usp) Reference Standard

174. Ethylamine 2-(diphenylmethoxy)-n, Compd. With 8-chlorotheophylline (1:1)

175. Theophylline, Compd. With 2-(diphenylmethoxy)-n,n-dimethylethylamine (1:1)

176. Dimenhydrinate For Peak Identification, European Pharmacopoeia (ep) Reference Standard

177. Dimenhydrinate, Pharmaceutical Secondary Standard; Certified Reference Material

178. Theophylline, Compd. With 2-(diphenylmethoxy)-n,n-(dimethylethyl)amine (1:1)

179. 1h-purine-2, 8-chloro-3,7-dihydro-1,3-dimethyl-, Compd. With 2-(diphenylmethoxy)-n,n-dimethylethanamine (1:1)

180. 8-chloro-1,3-dimethyl-1h-purine-2,6(3h,7h)-dione 2-(benzhydryloxy)-n,n-dimethylethanamine Salt

181. 8-chloro-1,3-dimethyl-1h-purine-2,6(3h,7h)-dionecompoundwith2-(benzhydryloxy)-n,n-dimethylethanamine(1:1)

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 470.0 g/mol
Molecular Formula C24H28ClN5O3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count5
Rotatable Bond Count6
Exact Mass469.1880675 g/mol
Monoisotopic Mass469.1880675 g/mol
Topological Polar Surface Area81.8 Ų
Heavy Atom Count33
Formal Charge0
Complexity509
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Therapeutic Uses

Antiemetics; Histamine H1 Antagonists

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


ABILITY TO INHIBIT EFFECTS OF HISTAMINE ON CAPILLARY PERMEABILITY & ON VASCULAR, BRONCHIAL, & MANY OTHER TYPES OF SMOOTH MUSCLE IS PROPERTY THAT CHARACTERIZES H1 ANTAGONISTS & THAT PROVIDES BASIS FOR THEIR PREVALENT CLINICAL USE... /ANTIHISTAMINES/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 603


"FLARE" COMPONENT OF TRIPLE RESPONSE & ITCHING CAUSED BY INTRADERMAL INJECTION OF HISTAMINE... H1-BLOCKING DRUGS SUPPRESS BOTH. ...HAVE LOCAL ANESTHETIC PROPERTIES... H1-BLOCKING DRUGS SELECTIVELY SUPPRESS STIMULANT EFFECT OF HISTAMINE ON ADRENAL CHROMAFFIN CELLS.../&/ AUTONOMIC GANGLION CELLS. /ANTIHISTAMINES/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 605


...EFFICACY...IN COUNTERING HYPERSENSITIVITY REACTIONS WILL VARY, DEPENDING ON DEG TO WHICH SYMPTOMS ARE DUE TO HISTAMINE. ...IN MAN...SOME PHENOMENA, INCL EDEMA FORMATION & ITCH, ARE FAIRLY WELL CONTROLLED; OTHERS, SUCH AS HYPOTENSION ARE LESS SO; & BRONCHOCONSTRICTION...LITTLE IF AT ALL. /ANTIHISTAMINES/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 605


For more Therapeutic Uses (Complete) data for DIMENHYDRINATE (12 total), please visit the HSDB record page.


4.2 Drug Warning

SEE ANTIHISTAMINICS. CONSIDERABLE MARGIN OF SAFETY SEPARATES THERAPEUTIC DOSE FROM USUAL LETHAL ONE. HOWEVER, BECAUSE CONVULSANT DOSE LIES NEAR LETHAL DOSE, CONVULSIONS INDICATE POOR PROGNOSIS. ADULTS HAVE SURVIVED SINGLE DOSES OF 2.5-5.0 G. CHILDREN...30-60 MG/KG HAS PRODUCED...POISONINGS. /ANTIHISTAMINICS/

Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-231


IN THERAPEUTIC DOSES, ALL H1 ANTAGONISTS ELICIT SIDE EFFECTS. ...RARELY SERIOUS & OFTEN DISAPPEAR...SOMETIMES...DRUG MUST BE WITHDRAWN. SOME DIFFERENCE...WITH DIFFERENT PREPN IS DISCERNIBLE...MARKED VARIATION IN RESPONSES OF INDIVIDUAL SUBJECTS... /ANTIHISTAMINES/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 607


...ANTICHOLINERGIC ACTIVITY, WHICH ACCOUNTS FOR DRYNESS OF MOUTH...&... DIFFICULTY IN MICTURATION & IMPOTENCE. SOME INTENSIFY RESPONSES TO NOREPINEPHRINE OR STIMULATION OF ADRENERGIC NERVES & INHIBIT RESPONSES TO TYRAMINE... RAPID IV INJECTION OF H1 ANTAGONISTS CAUSES TRANSIENT FALL IN BLOOD PRESSURE... /ANTIHISTAMINES/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 606


H1 ANTAGONISTS CAN BOTH STIMULATE & DEPRESS CNS. ...CENTRAL EXCITATION IS STRIKING FEATURE OF POISONING WITH ANTIHISTAMINES & CAN RESULT IN CONVULSIONS, PARTICULARLY IN INFANTS. CENTRAL DEPRESSION...IS USUAL ACCOMPANIMENT OF THERAPEUTIC DOSES. /ANTIHISTAMINES/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 606


PERSONS TAKING ANTIHISTAMINES SHOULD BE ALERTED TO THEIR SEDATIVE EFFECTS & SHOULD BE CAUTIONED NOT TO DRIVE AN AUTOMOBILE, FLY AN AIRPLANE, OR OPERATE HAZARDOUS MACHINERY... /ANTIHISTAMINES/

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1057


4.3 Drug Indication

Dimenhydrinate is indicated for the prevention and treatment of nausea, vomiting, or vertigo of motion sickness.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Dimenhydrinate is indicated for the prevention and treatment of nausea, vomiting, or vertigo of motion sickness. It has a short duration of action of 4-8 hours. Patients should be counselled regarding pronounced drowsiness, avoiding alcohol and other sedatives, and exercising caution when operating a motor vehicle or heavy machinery.


5.2 MeSH Pharmacological Classification

Antiemetics

Drugs used to prevent NAUSEA or VOMITING. (See all compounds classified as Antiemetics.)


Histamine H1 Antagonists

Drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine. Included here are the classical antihistaminics that antagonize or prevent the action of histamine mainly in immediate hypersensitivity. They act in the bronchi, capillaries, and some other smooth muscles, and are used to prevent or allay motion sickness, seasonal rhinitis, and allergic dermatitis and to induce somnolence. The effects of blocking central nervous system H1 receptors are not as well understood. (See all compounds classified as Histamine H1 Antagonists.)


5.3 FDA Pharmacological Classification
5.3.1 Pharmacological Classes
Histamine-1 Receptor Antagonist [EPC]; Histamine H1 Receptor Antagonists [MoA]
5.4 ATC Code

R - Respiratory system

R06 - Antihistamines for systemic use

R06A - Antihistamines for systemic use

R06AA - Aminoalkyl ethers

R06AA11 - Dimenhydrinate


5.5 Absorption, Distribution and Excretion

Absorption

A 50 mg oral film coated tablet reaches a Cmax of 72.6 ng/mL with a Tmax of 2.7 hours. A 100 mg suppository reaches a Cmax of 112.2 ng/mL with a Tmax of 5.3 hours.


Route of Elimination

Dimenhydrinate is predominantly eliminated in the urine. 1-3% of the dissociated diphenhydramine is eliminated in the urine unchanged, while 64% of diphenhydramine is eliminated in the urine as metabolites. The elimination of dimenhydrinate has not been fully studied.


Volume of Distribution

The volume of distribution of dimenhydrinate is 3-4 L/kg.


DIMENHYDRINATE (ETHANOLAMINES): DURATION OF ACTION (HR) 4-6. /FROM TABLE/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 609


H1 ANTAGONISTS ARE READILY ABSORBED FROM GI TRACT & PARENTERAL SITES OF ADMIN. FOLLOWING ORAL ADMIN, EFFECTS START WITHIN 15 TO 30 MIN, ARE FULLY DEVELOPED WITHIN 1 HR, & LAST ABOUT 3 TO 6 HR, ALTHOUGH SOME...ACT LONGER. /ANTIHISTAMINES/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 607


5.6 Metabolism/Metabolites

Dimenhydrinate is a theoclate salt that separates into [diphenhydramine] and [8-chlorotheophylline]. diphenhydramine can either be N-glucuronidated by UGTs to diphenhydramine N-glucuronide or N-demethylated by CYP2D6, CYP1A2, CYP2C9, and CYP2C19 to N-desmethyldiphenhydramine. N-desmethyldiphenhydramine can be N-demethylated again by the same enzymes to N,N-didesmethyldiphenhydramine, which undergoes oxidative deamination to form diphenylmethoxyacetic acid.


EXTENSIVE STUDIES OF METABOLIC FATE OF ANTIHISTAMINES HAVE BEEN LIMITED TO A FEW COMPD. ... MAIN SITE OF METABOLIC TRANSFORMATION IS LIVER. /ANTIHISTAMINES/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 607


5.7 Biological Half-Life

The plasma elimination half life of dimenhydrinate is 5-8 hours.


5.8 Mechanism of Action

Dimenhydrinate is a theoclate salt that separates into [diphenhydramine] and [8-chlorotheophylline]. While the exact mechanism of action is unknown, diphenhydramine is theorized to reduce disturbances to equilibrium through antimuscarinic effects or histamine H1 antagonism. 8-chlorotheophylline may produce excitation through blocking adenosine receptors, reducing the drowsiness produced by diphenhydramine.


IT IS ESSENTIAL TO NOTE THAT NEITHER H1...BLOCKERS INHIBIT HISTAMINE RELEASE. ...EFFECTS OF HISTAMINE ANTAGONISTS...FACILITATE RELEASE. BENEFICIAL EFFECTS OF HISTAMINE ANTAGONISTS ARE THUS CONFINED TO ANTAGONISM OF RESPONSES TO HISTAMINE THAT IS RELEASED. /ANTIHISTAMINES/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 605


DRUGS USED TO BLOCK HISTAMINE RECEPTORS FALL INTO THAT LARGE GROUP OF PHARMACOLOGICAL ANTAGONISTS THAT APPEAR TO ACT BY OCCUPYING "RECEPTIVE SITES" ON EFFECTOR CELL, TO EXCLUSION OF AGONIST MOLECULES, WITHOUT THEMSELVES INITIATING RESPONSE. TYPICALLY...COMPETITIVE & REVERSIBLE. /ANTIHISTAMINES/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 603


...ANTIHISTAMINES EFFECTIVE IN MOTION SICKNESS ACT BY VIRTUE OF CENTRAL ANTAGONISM OF ACH... ACT BY BLOCKING EXCITATORY LABYRINTHINE IMPULSES @ CHOLINERGIC SYNAPSES IN REGION OF VESTIBULAR NUCLEI. /ANTIHISTAMINES/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 606


...MOTION SICKNESS. ...STIMULATION OF VESTIBULAR APPARATUS...& THAT VESTIBULAR CEREBELLAR MIDBRAIN "INTEGRATIVE VOMITING CENTER" & MEDULLARY CHEMORECEPTIVE TRIGGER ZONE ARE SOMEHOW INVOLVED. /ANTIHISTAMINES/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 606


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27-Jan-2021
14-Aug-2024
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