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    Chemistry

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    Also known as: 554-92-7, Trimethobenzamide hcl, Tigan, Nauseton, Ametik hydrochloride, Ro 2-9578
    Molecular Formula
    C21H29ClN2O5
    Molecular Weight
    424.9  g/mol
    InChI Key
    WIIZEEPFHXAUND-UHFFFAOYSA-N
    FDA UNII
    WDQ5P1SX7Q
    Trimethobenzamide HCl
    Trimethobenzamide Hydrochloride is the hydrochloride salt form of trimethobenzamide, a benzamide derivative with an antiemetic property. Although the mechanism of action is largely unknown, it inhibits the chemoreceptor trigger zone (CTZ), an area in the medulla oblongata through which emetic impulses are conveyed to the vomiting center, thereby suppressing nausea and vomiting.
    1 2D Structure

    Trimethobenzamide HCl

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    N-[[4-[2-(dimethylamino)ethoxy]phenyl]methyl]-3,4,5-trimethoxybenzamide;hydrochloride
    2.1.2 InChI
    InChI=1S/C21H28N2O5.ClH/c1-23(2)10-11-28-17-8-6-15(7-9-17)14-22-21(24)16-12-18(25-3)20(27-5)19(13-16)26-4;/h6-9,12-13H,10-11,14H2,1-5H3,(H,22,24);1H
    2.1.3 InChI Key
    WIIZEEPFHXAUND-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CN(C)CCOC1=CC=C(C=C1)CNC(=O)C2=CC(=C(C(=C2)OC)OC)OC.Cl
    2.2 Other Identifiers
    2.2.1 UNII
    WDQ5P1SX7Q
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. T-gen

    2. Tebamide

    3. Ticon

    4. Tigan

    5. Trimethobenzamide

    6. Trimethobenzamide Monohydrochloride

    2.3.2 Depositor-Supplied Synonyms

    1. 554-92-7

    2. Trimethobenzamide Hcl

    3. Tigan

    4. Nauseton

    5. Ametik Hydrochloride

    6. Ro 2-9578

    7. N-(4-(2-(dimethylamino)ethoxy)benzyl)-3,4,5-trimethoxybenzamide Hydrochloride

    8. Tribenzagan Hydrochloride

    9. Nsc-37882

    10. Wdq5p1sx7q

    11. Trimethobenzamide Hydrochloride [usp]

    12. Poligerim

    13. Tebamide

    14. Trimethobenzamide (hydrochloride)

    15. N-(p-(2-(dimethylamino)ethoxy)benzyl)-3,4,5-trimethoxybenzamide Monohydrochloride

    16. Benzamide, N-((4-(2-(dimethylamino)ethoxy)phenyl)methyl)-3,4,5-trimethoxy-, Monohydrochloride

    17. N-[[4-[2-(dimethylamino)ethoxy]phenyl]methyl]-3,4,5-trimethoxybenzamide;hydrochloride

    18. 554-92-7 (hcl)

    19. Ibikin

    20. Anaus

    21. Ticon

    22. Dsstox_cid_27754

    23. Dsstox_rid_82531

    24. Dsstox_gsid_47774

    25. T-gen

    26. Trimethobenzamide Hydrochloride (usp)

    27. N-{[4-(2-dimethylaminoethoxy)phenyl]methyl}-3,4,5-trimethoxy-benzamide Hydrochloride

    28. Ncgc00016509-01

    29. Trimethobenzamidehydrochloride

    30. Cas-554-92-7

    31. Einecs 209-075-6

    32. Unii-wdq5p1sx7q

    33. Nsc 37882

    34. N-[4-[2-(dimethylamino)ethoxy]benzyl]-3,4,5-trimethoxybenzamide Hydrochloride

    35. Prestwick_526

    36. Trimethobenzamidehcl

    37. 4-(2-dimethylaminoethoxy)-n-(3,4,5-trimethoxybenzoyl)benzylamine Hydrochloride

    38. N-(p-(2-(dimethylamino)ethoxy)benzyl)-3,4,5-trimethoxybenzamide Hydrochloride

    39. Schembl41339

    40. Mls002154193

    41. Spectrum1500594

    42. Chembl1200887

    43. Dtxsid7047774

    44. Hms1568o21

    45. Hms1921g21

    46. Pharmakon1600-01500594

    47. Nsc37882

    48. Tox21_110465

    49. Ccg-40276

    50. Hy-12751a

    51. Mfcd00057999

    52. Nsc757359

    53. S5483

    54. Akos022172835

    55. Tox21_110465_1

    56. Cs-7696

    57. Nsc-757359

    58. Benzamide, N-(p-(2-(dimethylamino)ethoxy)benzyl)-3,4,5-trimethoxy-, Hydrochloride

    59. Benzamide, N-(p-(2-(dimethylamino)ethoxy)benzyl)-3,4,5-trimethoxy-, Monohydrochloride

    60. Benzamide,n-[[4-[2-(dimethylamino)ethoxy]phenyl]methyl]-3,4,5-trimethoxy-,monohydrochloride

    61. Ncgc00016509-06

    62. Ncgc00094803-01

    63. Ncgc00094803-02

    64. Benzamide,4,5-trimethoxy-, Hydrochloride

    65. Bs-17063

    66. Smr001233483

    67. Trimethobenzamide Hydrochloride [mi]

    68. Benzamide,4,5-trimethoxy-, Monohydrochloride

    69. Ft-0736653

    70. T3525

    71. Trimethobenzamide Hydrochloride [vandf]

    72. C75602

    73. D02733

    74. Trimethobenzamide Hydrochloride [mart.]

    75. Trimethobenzamide Hydrochloride [usp-rs]

    76. Trimethobenzamide Hydrochloride [who-dd]

    77. Wln: 1or Bo1 Co1 Evm1r Do2n1&1 &gh

    78. 554t927

    79. A870178

    80. Sr-05000001733-3

    81. Trimethobenzamide Hydrochloride [orange Book]

    82. Q27292581

    83. Trimethobenzamide Hydrochloride [usp Monograph]

    84. N-[p-[2-(dimethylamino)ethoxy]benzyl]-3,5-trimethoxybenzamide Hydrochloride

    85. 4-[(2-dimethylamino)ethoxy]-n-(3,5-trimethoxybenzoyl)benzylamine Hydrochloride

    86. N-[[4-[2-(dimethylamino)ethoxy]phenyl]methyl]-3,4,5-trimethoxybenzamide Monohydrochloride

    2.4 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 424.9 g/mol
    Molecular Formula C21H29ClN2O5
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count10
    Exact Mass424.1764997 g/mol
    Monoisotopic Mass424.1764997 g/mol
    Topological Polar Surface Area69.3 Ų
    Heavy Atom Count29
    Formal Charge0
    Complexity440
    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 NameTigan
    Drug LabelChemically, trimethobenzamide HCl is N-[p-[2-(dimethylamino)ethoxy]benzyl]-3,4,5-trimethoxybenzamide monohydrochloride. It has a molecular weight of 424.93 and the following structural formula: Capsules: Each 300-mg Tigan capsule for oral use conta...
    Active IngredientTrimethobenzamide hydrochloride
    Dosage FormCapsule; Injectable
    RouteInjection; Oral
    Strength300mg; 100mg/ml
    Market StatusPrescription
    CompanyPar Sterile Products; King Pharms

    2 of 4  
    Drug NameTrimethobenzamide hydrochloride
    PubMed HealthTrimethobenzamide (By mouth)
    Drug ClassesAntiemetic
    Drug LabelChemically, trimethobenzamide HCl is N-[p-[2-(dimethylamino)ethoxy]benzyl]-3,4,5-trimethoxybenzamide monohydrochloride. It has a molecular weight of 424.93 and the following structural formula: Capsules: Each 300-mg Tigan capsule for oral use conta...
    Active IngredientTrimethobenzamide hydrochloride
    Dosage FormCapsule; Injectable
    RouteInjection; Oral
    Strength300mg; 100mg/ml
    Market StatusPrescription
    CompanyMutual Pharma; Gavis Pharms; Luitpold

    3 of 4  
    Drug NameTigan
    Drug LabelChemically, trimethobenzamide HCl is N-[p-[2-(dimethylamino)ethoxy]benzyl]-3,4,5-trimethoxybenzamide monohydrochloride. It has a molecular weight of 424.93 and the following structural formula: Capsules: Each 300-mg Tigan capsule for oral use conta...
    Active IngredientTrimethobenzamide hydrochloride
    Dosage FormCapsule; Injectable
    RouteInjection; Oral
    Strength300mg; 100mg/ml
    Market StatusPrescription
    CompanyPar Sterile Products; King Pharms

    4 of 4  
    Drug NameTrimethobenzamide hydrochloride
    PubMed HealthTrimethobenzamide (By mouth)
    Drug ClassesAntiemetic
    Drug LabelChemically, trimethobenzamide HCl is N-[p-[2-(dimethylamino)ethoxy]benzyl]-3,4,5-trimethoxybenzamide monohydrochloride. It has a molecular weight of 424.93 and the following structural formula: Capsules: Each 300-mg Tigan capsule for oral use conta...
    Active IngredientTrimethobenzamide hydrochloride
    Dosage FormCapsule; Injectable
    RouteInjection; Oral
    Strength300mg; 100mg/ml
    Market StatusPrescription
    CompanyMutual Pharma; Gavis Pharms; Luitpold

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Antiemetics

    Drugs used to prevent NAUSEA or VOMITING. (See all compounds classified as Antiemetics.)

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Emesis Suppression [PE]; Antiemetic [EPC]

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    DOSAGE - INJECTABLE;INJECTION - 100MG/ML

    USFDA APPLICATION NUMBER - 17530

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    DOSAGE - CAPSULE;ORAL - 300MG **Federal Regis...DOSAGE - CAPSULE;ORAL - 300MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 17531

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