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Tox21_300992

Tox21_300992

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Also known as: 10347-81-6, Maprotiline hcl, Ludiomil, Psymion, Deprilept, 9-(gamma-methylaminopropyl)-9,10-dihydro-9,10-ethanoanthracene hydrochloride

Molecular Formula

C₂₀H₂₄ClN

Molecular Weight

313.9 g/mol

InChI Key

NZDMFGKECODQRY-UHFFFAOYSA-N

FDA UNII

7C8J54PVFI

A bridged-ring tetracyclic antidepressant that is both mechanistically and functionally similar to the tricyclic antidepressants, including side effects associated with its use.

1 2D Structure

Tox21_300992

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-methyl-3-(1-tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaenyl)propan-1-amine;hydrochloride

2.1.2 InChI

InChI=1S/C20H23N.ClH/c1-21-14-6-12-20-13-11-15(16-7-2-4-9-18(16)20)17-8-3-5-10-19(17)20;/h2-5,7-10,15,21H,6,11-14H2,1H3;1H

2.1.3 InChI Key

NZDMFGKECODQRY-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CNCCCC12CCC(C3=CC=CC=C31)C4=CC=CC=C24.Cl

2.2 Other Identifiers

2.2.1 UNII

7C8J54PVFI

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Ba-34,276

2. Ba34,276

3. Deprilept

4. Dibencycladine

5. Hydrochloride, Maprotiline

6. Ludiomil

7. Maprolu

8. Maprotilin

9. Maprotilin Holsten

10. Maprotilin Neuraxpharm

11. Maprotilin Ratiopharm

12. Maprotilin Teva

13. Maprotilin Von Ct

14. Maprotilin-neuraxpharm

15. Maprotilin-ratiopharm

16. Maprotilin-teva

17. Maprotiline

18. Maprotiline Mesylate

19. Mesylate, Maprotiline

20. Mirpan

21. N-methyl-9,10-ethanoanthracene-9(10h)-propylamine

22. Novo Maprotiline

23. Novo-maprotiline

24. Psymion

2.3.2 Depositor-Supplied Synonyms

1. 10347-81-6

2. Maprotiline Hcl

3. Ludiomil

4. Psymion

5. Deprilept

6. 9-(gamma-methylaminopropyl)-9,10-dihydro-9,10-ethanoanthracene Hydrochloride

7. Maprotilline Hcl

8. Maprotiline (hydrochloride)

9. Maprotiline, Hcl

10. Maprotiline Hydrochlorine

11. Nsc-757085

12. 9,10-ethanoanthracene-9(10h)-propanamine, N-methyl-, Hydrochloride

13. 7c8j54pvfi

14. Mls000069552

15. Mls000557000

16. N-methyl-9,10-ethanoanthracene-9(10h)-propanamine Hydrochloride

17. N-methyl-9,10-ethanoanthracene-9(10h)-propylamine Hydrochloride

18. 3-(9,10-ethanoanthracen-9(10h)-yl)-n-methylpropan-1-amine Hydrochloride

19. Ba-34,276

20. Smr000058834

21. Smr000148117

22. 1-(3-methylaminopropyl)dibenzo(b,e)bicyclo(2.2.2)octadiene Hydrochloride

23. Ba-34276

24. Ciba 34276 Ba

25. 1-(3-methylaminopropyl)dibenzo[b,e]bicyclo[2.2.2]octadienehydrochloride;1-(3-methylaminopropyl)dibenzo[b,e]bicyclo[2.2.2]octadienehydrochloride

26. Sr-01000076016

27. Einecs 233-758-8

28. Cas-10347-81-6

29. Unii-7c8j54pvfi

30. Ba 34276

31. Maprotilinehcl

32. Maprotiline Hydrochloride [jan]

33. 1-(3-methylaminopropyl)dibenzo[b,e]bicyclo[2.2.2]octadiene Hydrochloride

34. Ludiomil (tn)

35. Prestwick_749

36. Maprotiline Hydrochloride [usp:jan]

37. Mfcd00079464

38. Cpd000148117

39. Opera_id_513

40. Opera_id_1466

41. Dsstox_cid_24507

42. Dsstox_rid_80277

43. Dsstox_gsid_44507

44. Mls000758284

45. Mls001148189

46. Mls001423998

47. Schembl121014

48. Spectrum1500373

49. Regid_for_cid_71478

50. Chebi:6691

51. Chembl1200427

52. Chembl1237135

53. Dtxsid2044507

54. Maprotiline Hcl;ludiomil;psymion

55. Ba-34276 Hydrochloride

56. Hms1569e13

57. Hms1920j13

58. Kuc112481c

59. Pharmakon1600-01500373

60. Maprotiline, Ludiomil Hydrochloride

61. Bcp23366

62. Hy-b0444

63. Str09724

64. Tox21_300992

65. Tox21_500812

66. 9,10-ethanoanthracene-9(10h)-propylamine, N-methyl-, Hydrochloride

67. Ccg-38957

68. Nsc757085

69. S2517

70. Maprotiline Hydrochloride [mi]

71. Akos015961872

72. Akos015994755

73. Maprotiline Hydrochloride (jp17/usp)

74. Ac-8249

75. Bcp9000894

76. Ccg-220346

77. Ks-5095

78. Lp00812

79. Nc00056

80. Nsc 757085

81. Maprotiline Hydrochloride [mart.]

82. Maprotiline Hydrochloride [vandf]

83. Ncgc00094145-01

84. Ncgc00094145-02

85. Ncgc00094145-03

86. Ncgc00094145-04

87. Ncgc00254894-01

88. Ncgc00261497-01

89. Bm164655

90. Ksc-315-031-

91. Maprotiline Hydrochloride [usp-rs]

92. Maprotiline Hydrochloride [who-dd]

93. Bcp0726000234

94. Eu-0100812

95. Ft-0659758

96. M2527

97. Sw196892-3

98. D00818

99. M 9651

100. Maprotiline Hydrochloride [ep Monograph]

101. Maprotiline Hydrochloride [orange Book]

102. T71539

103. Maprotiline Hydrochloride [usp Monograph]

104. Maprotiline Hydrochloride, >99% (hplc), Powder

105. 347m816

106. A907819

107. Sr-01000000134

108. J-000980

109. Sr-01000000134-3

110. Sr-01000076016-1

111. Sr-01000076016-3

112. Q27268058

113. Maprotiline Hydrochloride 1.0 Mg/ml In Methanol (as Free Base)

114. 3-(9,10-ethanoanthracen-9(10h)-yl)-n-methylpropan-1-aminehydrochloride

115. Maprotiline Hydrochloride, European Pharmacopoeia (ep) Reference Standard

116. Maprotiline Hydrochloride, United States Pharmacopeia (usp) Reference Standard

117. Hydron;n-methyl-3-(1-tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaenyl)propan-1-amine;chloride

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

119. Methyl(3-{tetracyclo[6.6.2.0(2),?.0?,(1)?]hexadeca-2,4,6,9,11,13-hexaen-1-yl}propyl)amine Hydrochloride

120. Methyl(3-{tetracyclo[6.6.2.0^{2,7}.0^{9,14}]hexadeca-2(7),3,5,9(14),10,12-hexaen-1-yl}propyl)amine Hydrochloride

121. N-methyl-3-(1-tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaenyl)propan-1-amine;hydrochloride

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₂₄ClN
Molecular Weight	313.9 g/mol
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	4
Exact Mass	313.1597275 g/mol
Monoisotopic Mass	313.1597275 g/mol
Topological Polar Surface Area	12 Å²
Heavy Atom Count	22
Formal Charge	0
Complexity	339
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Maprotiline hydrochloride
Drug Label	Maprotiline hydrochloride, USP is a tetracyclic antidepressant, available as 25 mg, 50 mg and 75 mg tablets for oral administration. Its chemical name is N-methyl-9,10-ethanoanthracene-9(10H)-propylamine hydrochloride, and its structural formula is:C...
Active Ingredient	Maprotiline hydrochloride
Dosage Form	Tablet
Route	Oral
Strength	25mg; 75mg; 50mg
Market Status	Prescription
Company	Mylan

2 of 2
Drug Name	Maprotiline hydrochloride
Drug Label	Maprotiline hydrochloride, USP is a tetracyclic antidepressant, available as 25 mg, 50 mg and 75 mg tablets for oral administration. Its chemical name is N-methyl-9,10-ethanoanthracene-9(10H)-propylamine hydrochloride, and its structural formula is:C...
Active Ingredient	Maprotiline hydrochloride
Dosage Form	Tablet
Route	Oral
Strength	25mg; 75mg; 50mg
Market Status	Prescription
Company	Mylan

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, Second-Generation

A structurally and mechanistically diverse group of drugs that are not tricyclics or monoamine oxidase inhibitors. The most clinically important appear to act selectively on serotonergic systems, especially by inhibiting serotonin reuptake. (See all compounds classified as Antidepressive Agents, Second-Generation.)

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