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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]

API Reference Price

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18-Jan-2021
31-Aug-2024
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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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