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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
    MAPROTILINE HYDROCHLORIDE
    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

    MAPROTILINE HYDROCHLORIDE

    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 Weight 313.9 g/mol
    Molecular Formula C20H24ClN
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count1
    Rotatable Bond Count4
    Exact Mass313.1597275 g/mol
    Monoisotopic Mass313.1597275 g/mol
    Topological Polar Surface Area12 Ų
    Heavy Atom Count22
    Formal Charge0
    Complexity339
    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 2  
    Drug NameMaprotiline hydrochloride
    Drug LabelMaprotiline 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 IngredientMaprotiline hydrochloride
    Dosage FormTablet
    RouteOral
    Strength25mg; 75mg; 50mg
    Market StatusPrescription
    CompanyMylan

    2 of 2  
    Drug NameMaprotiline hydrochloride
    Drug LabelMaprotiline 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 IngredientMaprotiline hydrochloride
    Dosage FormTablet
    RouteOral
    Strength25mg; 75mg; 50mg
    Market StatusPrescription
    CompanyMylan

    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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