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Chemistry

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Also known as: 113-52-0, Imipramine hcl, Tofranil, Pryleugan, Imizine, Chimoreptin
Molecular Formula
C19H25ClN2
Molecular Weight
316.9  g/mol
InChI Key
XZZXIYZZBJDEEP-UHFFFAOYSA-N
FDA UNII
BKE5Q1J60U

Imipramine Hydrochloride
The prototypical tricyclic antidepressant. It has been used in major depression, dysthymia, bipolar depression, attention-deficit disorders, agoraphobia, and panic disorders. It has less sedative effect than some other members of this therapeutic group.
1 2D Structure

Imipramine Hydrochloride

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N,N-dimethylpropan-1-amine;hydrochloride
2.1.2 InChI
InChI=1S/C19H24N2.ClH/c1-20(2)14-7-15-21-18-10-5-3-8-16(18)12-13-17-9-4-6-11-19(17)21;/h3-6,8-11H,7,12-15H2,1-2H3;1H
2.1.3 InChI Key
XZZXIYZZBJDEEP-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CN(C)CCCN1C2=CC=CC=C2CCC3=CC=CC=C31.Cl
2.2 Other Identifiers
2.2.1 UNII
BKE5Q1J60U
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 4,4'-methylenebis(3-hydroxy-2-naphthoic Acid)-3-(10,11-dihydro-5h-dibenzo(b,f)azepin-5-yl)-n,n-dimethyl-1-propanamine (1:2)

2. Imidobenzyle

3. Imipramine

4. Imipramine Monohydrochloride

5. Imipramine Pamoate

6. Imizin

7. Janimine

8. Melipramine

9. Norchlorimipramine

10. Pryleugan

11. Tofranil

2.3.2 Depositor-Supplied Synonyms

1. 113-52-0

2. Imipramine Hcl

3. Tofranil

4. Pryleugan

5. Imizine

6. Chimoreptin

7. Chrytemin

8. Presamine

9. Feinalmin

10. Imilanyle

11. Persamine

12. Pertofram

13. Teperine

14. Tofranile

15. Iprogen

16. Janimine

17. Pramine

18. Imp Hydrochloride

19. Ia-pram

20. Imizin

21. Co Cap Imipramine 25

22. Melipramine Hcl

23. Antideprin Hydrochloride

24. Imipramini Hydrochloridum

25. Imipramine Monohydrochloride

26. Imizinum

27. Imidol

28. Imipramine (hydrochloride)

29. G 22355

30. 3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)-n,n-dimethylpropan-1-amine;hydrochloride

31. Nsc-114900

32. N-(3-dimethylaminopropyl)iminodibenzyl Hydrochloride

33. Bke5q1j60u

34. Mls000028430

35. Chebi:5882

36. Deprinol

37. 3-(10,11-dihydro-5h-dibenzo[b,f]azepin-5-yl)-n,n-dimethylpropan-1-amine Hydrochloride

38. 5-(3-(dimethylamino)propyl)-10,11-dihydro-5h-dibenz(b,f)azepine Monohydrochloride

39. 5h-dibenz(b,f)azepine-5-propanamine, 10,11-dihydro-n,n-dimethyl-, Monohydrochloride

40. Sk-pramine

41. Psicopramine

42. Thymopramin

43. Dynazina

44. Efuranol

45. Fujisawa

46. Imipramini

47. Odeoxil

48. Smr000058388

49. Tipramine

50. Venefon

51. Vionyl

52. Tofranil (tn)

53. 5h-dibenz[b,f]azepine-5-propanamine, 10,11-dihydro-n,n-dimethyl-, Monohydrochloride

54. G-22355

55. Imipram

56. Sk-pramine Hydrochloride

57. Imipramine Hydrochloride [jan]

58. Melipramine Hydrochloride

59. Sr-01000003064

60. Cas-113-52-0

61. Einecs 204-030-7

62. Mfcd00012669

63. Unii-bke5q1j60u

64. Nsc 114900

65. Imipraminehcl

66. Sk-pramine Hcl

67. Prestwick_277

68. Imipramine Hydrochloride [usp:jan]

69. Nebumetone Impurity D

70. N-(gamma-dimethylaminopropyl)iminodibenzyl Hydrochloride

71. 3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)-n,n-dimethyl-propan-1-amine

72. Cpd000058388

73. Opera_id_319

74. N-(gamma-dimetilaminopropil)-iminodibenzile Cloridrato [italian]

75. Surecn41766

76. Imipramine Hydrochloride Rs

77. 5-(3-dimethylaminopropyl)-10,11-dihydro-5h-dibenz(b,f)azepine Hydrochloride

78. 5h-dibenz(b,f)azepine, 10,11-dihydro-5-(3-(dimethylamino)propyl)-, Hydrochloride

79. Chembl1692

80. Dsstox_cid_20738

81. Dsstox_rid_79581

82. Dsstox_gsid_40738

83. G 22150

84. Regid_for_cid_8228

85. Schembl41765

86. Mls001146891

87. Mls002222195

88. Spectrum1500348

89. N-(gamma-dimetilaminopropil)-iminodibenzile Cloridrato

90. Dtxsid7040738

91. Imipramine For System Suitability

92. Hms1568o05

93. Hms1920f17

94. Pharmakon1600-01500348

95. Hy-b1490

96. Tox21_301417

97. Tox21_500702

98. Ccg-40208

99. Imipramine Hydrochloride [mi]

100. Nsc114900

101. Nsc757074

102. S4377

103. Imipramine Hydrochloride (jp17/usp)

104. Akos015895330

105. Ac-7587

106. Cs-6180

107. Ks-1072

108. Lp00702

109. Nc00570

110. Nsc-757074

111. 5h-dibenz(b,f)azepine, 5-(3-(dimethylamino)propyl)-10,11-dihydro-, Monohydrochloride

112. Imipramine Hydrochloride [mart.]

113. Imipramine Hydrochloride [vandf]

114. Imipramine Hydrochloride [usp-rs]

115. Imipramine Hydrochloride [who-dd]

116. Imipramine Hydrochloride [who-ip]

117. Ncgc00024253-05

118. Ncgc00094054-01

119. Ncgc00094054-02

120. Ncgc00094054-03

121. Ncgc00094054-04

122. Ncgc00094054-05

123. Ncgc00255651-01

124. Ncgc00261387-01

125. (3-{2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaen-2-yl}propyl)dimethylamine Hydrochloride

126. Bi164574

127. Imipramine Hydrochloride, >=99% (tlc)

128. Db-041172

129. Eu-0100702

130. Ft-0631652

131. Ft-0670318

132. I0971

133. St50985122

134. Sw196582-4

135. Imipramine Hydrochloride [orange Book]

136. C07982

137. D00815

138. I 7379

139. Imipramine Hydrochloride [ep Monograph]

140. Imipramine Hydrochloride [usp Impurity]

141. Imipramine Hydrochloride [usp Monograph]

142. Imipramini Hydrochloridum [who-ip Latin]

143. 113i520

144. Imipramine Hydrochloride, Bioxtra, >=99% (tlc)

145. Imipramine Hydrochloride, Sigma Reference Standard

146. J-002975

147. Lmipramine Hydrochloride 100 Microg/ml In Methanol

148. Q-200878

149. Sr-01000003064-2

150. Sr-01000003064-7

151. 5-(3-dimethylaminopropyl)-10,f)azepine Hydrochloride

152. Q27106923

153. Wln: T C676 Bn & T & J B3n1 & 1 & Gh

154. Z1551429721

155. N-(.gamma.-dimethylaminopropyl)iminodibenzyl Hydrochloride

156. 5h-dibenz[b, 10,11-dihydro-n,n-dimethyl-, Monohydrochloride

157. Imipramine Hydrochloride 1.0 Mg/ml In Methanol (as Free Base)

158. 5h-dibenz[b, 10,11-dihydro-5-[3-(dimethylamino)propyl]-, Hydrochloride

159. Imipramine Hydrochloride, European Pharmacopoeia (ep) Reference Standard

160. 10,11-dihydro-n,n-dimethyl-5h-dibenzo[b,f]azepine-5-propanamine Hydrochloride

161. 5-(3-dimethylaminopropyl)-10,11-dihydro-5h-dibenz-[b,f]-azepine, Hydrochloride

162. 5-[3-(dimethylamino)propyl]-10,11-dihydro-5h-dibenzo[b,f]azepine Hydrochloride

163. 5h-dibenz(b,f)azepine-5-propanamine, 10,11-dihydro-n,n-dimethyl-, Hydrochloride (1:1)

164. 5h-dibenz[b, 5-[3-(dimethylamino)propyl]-10,11-dihydro-, Monohydrochloride

165. Imipramine For System Suitability, European Pharmacopoeia (ep) Reference Standard

166. Imipramine Hydrochloride, Pharmaceutical Secondary Standard; Certified Reference Material

167. Imipramine Hydrochloride, United States Pharmacopeia (usp) Reference Standard

168. (3-{2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-yl}propyl)dimethylamine Hydrochloride

169. Imipramine Hydrochloride Solution, 1.0 Mg/ml In Methanol (as Free Base), Ampule Of 1 Ml, Certified Reference Material

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 316.9 g/mol
Molecular Formula C19H25ClN2
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count4
Exact Mass316.1706265 g/mol
Monoisotopic Mass316.1706265 g/mol
Topological Polar Surface Area6.5 Ų
Heavy Atom Count22
Formal Charge0
Complexity291
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 Drug Information
1 of 4  
Drug NameImipramine hydrochloride
PubMed HealthImipramine (By mouth)
Drug ClassesAntidepressant, Urinary Enuresis Agent
Drug LabelImipramine hydrochloride, the original tricyclic antidepressant, is a member of the dibenzazepine group of compounds. It is designated 5-[3-(Dimethylamino) propyl]-10, 11-dihydro-5H-dibenz [b,f]-azepine monohydrochloride. Structurally, it may be repr...
Active IngredientImipramine hydrochloride
Dosage FormTablet
RouteOral
Strength25mg; 50mg; 10mg
Market StatusPrescription
CompanyExcellium; Lupin; Sandoz; Par Pharm; Mutual Pharm

2 of 4  
Drug NameTofranil
Drug LabelTofranil is supplied in tablet form for oral administration.Tofranil, imipramine hydrochloride USP, the original tricyclic antidepressant, is a member of the dibenzazepine group of compounds. It is designated 5-3-(dimethylamino)propyl-10,11-dihydr...
Active IngredientImipramine hydrochloride
Dosage FormTablet
RouteOral
Strength25mg; 50mg; 10mg
Market StatusPrescription
CompanyMallinckrodt

3 of 4  
Drug NameImipramine hydrochloride
PubMed HealthImipramine (By mouth)
Drug ClassesAntidepressant, Urinary Enuresis Agent
Drug LabelImipramine hydrochloride, the original tricyclic antidepressant, is a member of the dibenzazepine group of compounds. It is designated 5-[3-(Dimethylamino) propyl]-10, 11-dihydro-5H-dibenz [b,f]-azepine monohydrochloride. Structurally, it may be repr...
Active IngredientImipramine hydrochloride
Dosage FormTablet
RouteOral
Strength25mg; 50mg; 10mg
Market StatusPrescription
CompanyExcellium; Lupin; Sandoz; Par Pharm; Mutual Pharm

4 of 4  
Drug NameTofranil
Drug LabelTofranil is supplied in tablet form for oral administration.Tofranil, imipramine hydrochloride USP, the original tricyclic antidepressant, is a member of the dibenzazepine group of compounds. It is designated 5-3-(dimethylamino)propyl-10,11-dihydr...
Active IngredientImipramine hydrochloride
Dosage FormTablet
RouteOral
Strength25mg; 50mg; 10mg
Market StatusPrescription
CompanyMallinckrodt

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Adrenergic Uptake Inhibitors

Drugs that block the transport of adrenergic transmitters into axon terminals or into storage vesicles within terminals. The tricyclic antidepressants (ANTIDEPRESSIVE AGENTS, TRICYCLIC) and amphetamines are among the therapeutically important drugs that may act via inhibition of adrenergic transport. Many of these drugs also block transport of serotonin. (See all compounds classified as Adrenergic Uptake Inhibitors.)


Antidepressive Agents, Tricyclic

Substances that contain a fused three-ring moiety and are used in the treatment of depression. These drugs block the uptake of norepinephrine and serotonin into axon terminals and may block some subtypes of serotonin, adrenergic, and histamine receptors. However, the mechanism of their antidepressant effects is not clear because the therapeutic effects usually take weeks to develop and may reflect compensatory changes in the central nervous system. (See all compounds classified as Antidepressive Agents, Tricyclic.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Tricyclic Antidepressant [EPC]

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26-Feb-2021
27-Aug-2024
KGS
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DOSAGE - TABLET;ORAL - 10MG

USFDA APPLICATION NUMBER - 87846

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USFDA APPLICATION NUMBER - 87846

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