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Chemistry

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Also known as: 521-78-8, Trimipramine maleate salt, Surmontil maleate, Trimipramine (maleate), Trimipramine maleate, bp, Trimipramine hydrogen maleate
Molecular Formula
C24H30N2O4
Molecular Weight
410.5  g/mol
InChI Key
YDGHCKHAXOUQOS-BTJKTKAUSA-N
FDA UNII
I412286V22

Trimipramine
Tricyclic antidepressant similar to IMIPRAMINE, but with more antihistaminic and sedative properties.
1 2D Structure

Trimipramine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(Z)-but-2-enedioic acid;3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N,N,2-trimethylpropan-1-amine
2.1.2 InChI
InChI=1S/C20H26N2.C4H4O4/c1-16(14-21(2)3)15-22-19-10-6-4-8-17(19)12-13-18-9-5-7-11-20(18)22;5-3(6)1-2-4(7)8/h4-11,16H,12-15H2,1-3H3;1-2H,(H,5,6)(H,7,8)/b;2-1-
2.1.3 InChI Key
YDGHCKHAXOUQOS-BTJKTKAUSA-N
2.1.4 Canonical SMILES
CC(CN1C2=CC=CC=C2CCC3=CC=CC=C31)CN(C)C.C(=CC(=O)O)C(=O)O
2.1.5 Isomeric SMILES
CC(CN1C2=CC=CC=C2CCC3=CC=CC=C31)CN(C)C.C(=C\C(=O)O)\C(=O)O
2.2 Other Identifiers
2.2.1 UNII
I412286V22
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 10,11 Dihydro-n,n,beta-trimethyl-5h-dibenz(b,f)azepine-5-propanamine

2. Apo Trimip

3. Apo-trimip

4. Apotrimip

5. Beta, Trimipramin

6. Eldoral

7. Herphonal

8. Novo Tripramine

9. Novo-tripramine

10. Novotripramine

11. Nu Trimipramine

12. Nu-trimipramine

13. Nutrimipramine

14. Rhotrimine

15. Stangyl

16. Surmontil

17. Surmontil Maleate

18. Trimeprimine

19. Trimidura

20. Trimineurin

21. Trimineurin Maleate

22. Trimipramin Azu

23. Trimipramin Beta

24. Trimipramin Neurazpharm

25. Trimipramin Stada

26. Trimipramin-neurazpharm

27. Trimipramine

28. Trimipramine Maleate (1:1)

29. Trimipramine Maleate (1:1), (+)-isomer

30. Trimipramine Maleate (1:1), (+-)-isomer

31. Trimipramine Maleate (1:1), (-)-isomer

32. Trimipramine Mesylate

33. Trimipramine Monohydrochloride

34. Trimipramine, (+-)-isomer

35. Trimipramine, (-)-isomer

36. Trimipraminneurazpharm

2.3.2 Depositor-Supplied Synonyms

1. 521-78-8

2. Trimipramine Maleate Salt

3. Surmontil Maleate

4. Trimipramine (maleate)

5. Trimipramine Maleate, Bp

6. Trimipramine Hydrogen Maleate

7. Stangyl

8. (+)-trimipramine Maleate

9. (-)-trimipramine Maleate

10. Nsc-758386

11. Trimipramine Maleate, (+)-

12. Trimipramine Maleate, (-)-

13. 138283-61-1

14. 5-(3-(dimethylamino)-2-methylpropyl)-10,11-dihydro-5h-dibenz(b,f)azepine Maleate (1:1)

15. 269k6498ld

16. D28e1043w5

17. Trimeprimine Maleate

18. I412286v22

19. Trimeprimine Monomaleate

20. Dsstox_cid_25315

21. Dsstox_rid_80796

22. Trimipramini Maleas

23. Dsstox_gsid_45315

24. (z)-but-2-enedioic Acid;3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)-n,n,2-trimethylpropan-1-amine

25. 138283-60-0

26. Trimipramium Maleinicum

27. Trimipramine Acid Maleate

28. Chebi:35030

29. 10,11-dihydro-n,n,beta-trimethyl-5h-dibenz(b,f)azepine-5-propanamine (z)-2-butenedioate (1:1)

30. Sr-01000076152

31. Einecs 208-318-3

32. Unii-269k6498ld

33. Trimipraminemaleate

34. Surmontil (tn)

35. Prestwick_1022

36. Trimipramine Maleate [usan:usp:jan]

37. Trimipraminhydrogenmaleat

38. 3-(10,11-dihydro-5h-dibenzo[b,f]azepin-5-yl)-n,n,2-trimethylpropan-1-amine Maleate

39. Ncgc00016483-01

40. Cas-521-78-8

41. Schembl41289

42. 5h-dibenz(b,f)azepine-5-propanamine, 10,11-dihydro-n,n,beta-trimethyl-, (z)-2-butenedioate (1:1)

43. Mls001056765

44. Spectrum1503117

45. Chembl1200948

46. Dtxsid2045315

47. Unii-d28e1043w5

48. Hms500e15

49. Trimipramine Maleate (jan/usp)

50. Trimipramine Maleate [mi]

51. Hms1570b13

52. Hms1922g07

53. Hms2092l08

54. Hms2097b13

55. Hms2233h17

56. Hms3263h13

57. Hms3714b13

58. Pharmakon1600-01503117

59. Trimipramine Maleate [jan]

60. Unii-i412286v22

61. Trimipramine Maleate [usan]

62. Hy-b1213

63. Trimipramine For Peak Identification

64. Tox21_110449

65. Tox21_501156

66. Trimipramine Maleate [vandf]

67. Ccg-39308

68. Nsc758386

69. Trimipramine Maleate [mart.]

70. Trimipramine Maleate [usp-rs]

71. Trimipramine Maleate [who-dd]

72. Akos026750012

73. Tox21_110449_1

74. Cs-4840

75. Lp01156

76. Nsc 758386

77. 5h-dibenz(b,f)azepine, 10,11-dihydro-5-(3-(dimethylamino)-2-methylpropyl)-, Maleate (1:1)

78. Ncgc00016013-06

79. Ncgc00094418-01

80. Ncgc00094418-02

81. Ncgc00094418-03

82. Ncgc00094418-04

83. Ncgc00094418-05

84. Ncgc00261841-01

85. 1217260-65-5

86. Bs-17213

87. Smr000326720

88. Trimipramine Maleate [orange Book]

89. Trimipramine Maleate [ep Monograph]

90. Trimipramine Maleate [usp Monograph]

91. Eu-0101156

92. Sw197096-3

93. D02408

94. T 3146

95. Sr-01000076152-1

96. Sr-01000076152-4

97. Sr-01000076152-6

98. Q27116374

99. Trimipramine Maleate 1.0 Mg/ml In Methanol (as Free Base)

100. 10,11-dihydro-n,n,beta-trimethyl-5h-dibenz[b,f]azepine-5-propanamine(2z)-2-butenedioate

101. 5h-dibenz(b,f)azepine-5-propanamine, 10,11-dihydro-n,n,.beta.-trimethyl-, (+)-, (2z)-2-butenedioate (1:1)

102. 5h-dibenz(b,f)azepine-5-propanamine, 10,11-dihydro-n,n,.beta.-trimethyl-, (+)-, (z)-2-butenedioate (1:1)

103. 5h-dibenz(b,f)azepine-5-propanamine, 10,11-dihydro-n,n,.beta.-trimethyl-, (-)-, (2z)-2-butenedioate (1:1)

104. 5h-dibenz(b,f)azepine-5-propanamine, 10,11-dihydro-n,n,.beta.-trimethyl-, (-)-, (z)-2-butenedioate (1:1)

105. 5h-dibenz(b,f)azepine-5-propanamine, 10,11-dihydro-n,n,.beta.-trimethyl-, (z)-2-butenedioate (1:1)

106. 5h-dibenz(b,f)azepine-5-propanamine, 10,11-dihydro-n,n,beta-trimethyl-, (+)-, (2z)-2-butenedioate (1:1)

107. 5h-dibenz(b,f)azepine-5-propanamine, 10,11-dihydro-n,n,beta-trimethyl-, (+)-, (z)-2-butenedioate (1:1)

108. 5h-dibenz(b,f)azepine-5-propanamine, 10,11-dihydro-n,n,beta-trimethyl-, (-)-, (2z)-2-butenedioate (1:1)

109. 5h-dibenz(b,f)azepine-5-propanamine, 10,11-dihydro-n,n,beta-trimethyl-, (-)-, (z)-2-butenedioate (1:1)

110. 5h-dibenz(b,f)azepine-5-propanamine, 10,11-dihydro-n,n,beta-trimethyl-, (2z)-2-butenedioate (1:1)

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 410.5 g/mol
Molecular Formula C24H30N2O4
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count6
Exact Mass410.22055744 g/mol
Monoisotopic Mass410.22055744 g/mol
Topological Polar Surface Area81.1 Ų
Heavy Atom Count30
Formal Charge0
Complexity436
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameSurmontil
PubMed HealthTrimipramine (By mouth)
Drug ClassesAntidepreant
Drug LabelSURMONTIL (trimipramine maleate) is 5-(3-dimethylamino-2-methylpropyl)-10,11-dihydro-5H-dibenz (b,f) azepine acid maleate (racemic form). Molecular Formula: C20H26N2 C4H4O4 Molecular Weight: 410.5SURMONTIL capsules contain trimipramine maleate eq...
Active IngredientTrimipramine maleate
Dosage FormCapsule
RouteOral
Strengtheq 100mg base; eq 50mg base; eq 25mg base
Market StatusPrescription
CompanyOdyey Pharms

2 of 4  
Drug NameTrimipramine maleate
Drug LabelTrimipramine maleate is 5-(3-dimethylamino-2-methylpropyl)-10, 11-dihydro-5H-dibenz (b,f) azepine acid maleate (racemic form). Molecular Formula: C20H26N2 C4H4O4 Molecular Weight: 410.5Trimipramine maleate capsules contain tr...
Active IngredientTrimipramine maleate
Dosage FormCapsule
RouteOral
Strengtheq 100mg base; eq 50mg base; eq 25mg base
Market StatusPrescription
CompanyMikah Pharma

3 of 4  
Drug NameSurmontil
PubMed HealthTrimipramine (By mouth)
Drug ClassesAntidepreant
Drug LabelSURMONTIL (trimipramine maleate) is 5-(3-dimethylamino-2-methylpropyl)-10,11-dihydro-5H-dibenz (b,f) azepine acid maleate (racemic form). Molecular Formula: C20H26N2 C4H4O4 Molecular Weight: 410.5SURMONTIL capsules contain trimipramine maleate eq...
Active IngredientTrimipramine maleate
Dosage FormCapsule
RouteOral
Strengtheq 100mg base; eq 50mg base; eq 25mg base
Market StatusPrescription
CompanyOdyey Pharms

4 of 4  
Drug NameTrimipramine maleate
Drug LabelTrimipramine maleate is 5-(3-dimethylamino-2-methylpropyl)-10, 11-dihydro-5H-dibenz (b,f) azepine acid maleate (racemic form). Molecular Formula: C20H26N2 C4H4O4 Molecular Weight: 410.5Trimipramine maleate capsules contain tr...
Active IngredientTrimipramine maleate
Dosage FormCapsule
RouteOral
Strengtheq 100mg base; eq 50mg base; eq 25mg base
Market StatusPrescription
CompanyMikah Pharma

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

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.)


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.)


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

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DOSAGE - CAPSULE;ORAL - EQ 100MG BASE **Feder...DOSAGE - CAPSULE;ORAL - EQ 100MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 16792

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DOSAGE - CAPSULE;ORAL - EQ 25MG BASE **Federa...DOSAGE - CAPSULE;ORAL - EQ 25MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 16792

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DOSAGE - CAPSULE;ORAL - EQ 50MG BASE **Federa...DOSAGE - CAPSULE;ORAL - EQ 50MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 16792

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