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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

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