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2D Structure
Also known as: 7232-21-5, Maxolon, Metoclopramide hcl, Metoclopramide monohydrochloride, Cerucal, Paspertin
Molecular Formula
C14H23Cl2N3O2
Molecular Weight
336.3  g/mol
InChI Key
RVFUNJWWXKCWNS-UHFFFAOYSA-N
FDA UNII
7B1QZY5SWZ

A dopamine D2 antagonist that is used as an antiemetic.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-methoxybenzamide;hydrochloride
2.1.2 InChI
InChI=1S/C14H22ClN3O2.ClH/c1-4-18(5-2)7-6-17-14(19)10-8-11(15)12(16)9-13(10)20-3;/h8-9H,4-7,16H2,1-3H3,(H,17,19);1H
2.1.3 InChI Key
RVFUNJWWXKCWNS-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCN(CC)CCNC(=O)C1=CC(=C(C=C1OC)N)Cl.Cl
2.2 Other Identifiers
2.2.1 UNII
7B1QZY5SWZ
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 4-amino-5-chloro-n-(2-(diethylamino)ethyl)-2-methoxybenzamide

2. Cerucal

3. Dihydrochloride, Metoclopramide

4. Hydrochloride, Metoclopramide

5. Maxolon

6. Metaclopramide

7. Metoclopramide

8. Metoclopramide Dihydrochloride

9. Metoclopramide Monohydrochloride

10. Metoclopramide Monohydrochloride, Monohydrate

11. Monohydrochloride, Metoclopramide

12. Primperan

13. Reglan

14. Rimetin

2.3.2 Depositor-Supplied Synonyms

1. 7232-21-5

2. Maxolon

3. Metoclopramide Hcl

4. Metoclopramide Monohydrochloride

5. Cerucal

6. Paspertin

7. Clopra

8. Reglan

9. 4-amino-5-chloro-n-(2-(diethylamino)ethyl)-2-methoxybenzamide Hydrochloride

10. Metozolv

11. Metozolv Odt

12. Metoclopramide Hydrochloride Anhydrous

13. 7b1qzy5swz

14. Metoclopramide (hydrochloride)

15. Mls000069667

16. 4-amino-5-chloro-n-[2-(diethylamino)ethyl]-2-methoxybenzamide;hydrochloride

17. Benzamide, 4-amino-5-chloro-n-(2-(diethylamino)ethyl)-2-methoxy-, Monohydrochloride

18. Nsc-354467

19. Rimetin

20. Smr000058471

21. 4-amino-5-chloro-n-(2-(diethylamino)ethyl)-o-anisamide Hydrochloride

22. Primperan (tablet)

23. Metoclopramide Hydrochloride 100 Microg/ml In Acetonitrile

24. Metoclopramide Intensol

25. Reglan Odt

26. Ccris 7142

27. Sr-01000000165

28. Einecs 230-634-5

29. Unii-7b1qzy5swz

30. Nsc 354467

31. 4-amino-5-chloro-n-[2-(diethylamino)ethyl]-o-anisamide Hydrochloride

32. Prestwick_332

33. 4-amino-5-chloro-n-(2-diethylaminoethyl)-2-methoxy-benzamide

34. Mfcd00058011

35. Metoclopramidehcl

36. Opera_id_1671

37. Mls001074186

38. Mls002222202

39. O-anisamide, Monohydrochloride

40. Schembl205200

41. Spectrum1500410

42. Chembl1256771

43. Dtxsid10964306

44. Hms1568j19

45. Hms1920n15

46. Metoclopramide Hydrochloride, Solid

47. Pharmakon1600-01500410

48. Bcp28471

49. Tox21_500762

50. Nsc354467

51. Nsc757117

52. 4-amino-5-chloro-n-(2-diethylaminoethyl)-2-methoxybenzamide Hydrochloride

53. Akos015889947

54. O-anisamide, 4-amino-5-chloro-n-(2-(diethylamino)ethyl)-, Monohydrochloride

55. Ccg-212697

56. Hs-0006

57. Lp00762

58. Nc00519

59. 4-amino-5-chloro-n-(2-(diethylamino)ethyl)-2-methoxybenzamide Monohydrochloride

60. Ncgc00094102-01

61. Ncgc00094102-02

62. Ncgc00094102-03

63. Ncgc00094102-04

64. Ncgc00094102-05

65. Ncgc00261447-01

66. Wln: 2n2&2mvr Dz Cg Fo1 &gh

67. Eu-0100762

68. Ft-0657870

69. Ft-0672375

70. S4289

71. Sw196611-3

72. Vu0239518-5

73. A14247

74. M 0763

75. A923754

76. Sr-01000000165-2

77. Sr-01000000165-7

78. Q27267998

79. 4-amino-5-chloro-n-(2-diethylaminoethyl)-2-methoxybenzamide Hcl

80. 4-amino-5-chloro-n-(2-(diethylamino)ethyl)-o-anisamidmonohydrochloride

81. 4-amino-5-chloro-n-(2-(diethylamino)ethyl)-o-anisamide Monohydrochloride

82. Benzamide, 4-amino-5-chloro-n-(2-(diethylamino)ethyl)-2-methoxy-, Monohydrochloride (9ci)

83. Benzamide, 4-amino-5-chloro-n-[2-(diethylamino)ethyl]-2-methoxy-, Hydrochloride (1:1)

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 336.3 g/mol
Molecular Formula C14H23Cl2N3O2
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count4
Rotatable Bond Count7
Exact Mass335.1167324 g/mol
Monoisotopic Mass335.1167324 g/mol
Topological Polar Surface Area67.6 Ų
Heavy Atom Count21
Formal Charge0
Complexity300
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 NameMetoclopramide hydrochloride
Drug LabelMetoclopramide hydrochloride is a white or practically white, crystalline, odorless or practically odorless powder. It is very soluble in water, freely soluble in alcohol, sparingly soluble in chloroform, practically insoluble in ether. Chemically it...
Active IngredientMetoclopramide hydrochloride
Dosage FormTablet; Injectable; Tablet, orally disintegrating; Solution
RouteInjection; Oral
Strengtheq 5mg base; eq 5mg base/5ml; eq 5mg base/ml; eq 10mg base
Market StatusPrescription
CompanyVintage Pharms; Wockhardt; Silarx; Ani Pharms; Hospira; Teva; Pharm Assoc; Teva Pharms Usa; Northstar Hlthcare; Par Pharm; Novel Labs; Watson Labs; Vistapharm; Ipca Labs; Mutual Pharm; Bd Rx

2 of 4  
Drug NameMetozolv odt
PubMed HealthMetoclopramide
Drug ClassesAntiemetic, Diagnostic Agent, Stimulant, Gastrointestinal
Drug LabelMETOZOLV ODT is an orally disintegrating tablet formulation of metoclopramide hydrochloride. The 5 mg strength is a round white tablet debossed on one side with a 5 and plain on the other side; it is comprised of 5 mg metoclopramide (as 5.91...
Active IngredientMetoclopramide hydrochloride
Dosage FormTablet, orally disintegrating
RouteOral
Strengtheq 5mg base
Market StatusPrescription
CompanySalix Pharms

3 of 4  
Drug NameMetoclopramide hydrochloride
Drug LabelMetoclopramide hydrochloride is a white or practically white, crystalline, odorless or practically odorless powder. It is very soluble in water, freely soluble in alcohol, sparingly soluble in chloroform, practically insoluble in ether. Chemically it...
Active IngredientMetoclopramide hydrochloride
Dosage FormTablet; Injectable; Tablet, orally disintegrating; Solution
RouteInjection; Oral
Strengtheq 5mg base; eq 5mg base/5ml; eq 5mg base/ml; eq 10mg base
Market StatusPrescription
CompanyVintage Pharms; Wockhardt; Silarx; Ani Pharms; Hospira; Teva; Pharm Assoc; Teva Pharms Usa; Northstar Hlthcare; Par Pharm; Novel Labs; Watson Labs; Vistapharm; Ipca Labs; Mutual Pharm; Bd Rx

4 of 4  
Drug NameMetozolv odt
PubMed HealthMetoclopramide
Drug ClassesAntiemetic, Diagnostic Agent, Stimulant, Gastrointestinal
Drug LabelMETOZOLV ODT is an orally disintegrating tablet formulation of metoclopramide hydrochloride. The 5 mg strength is a round white tablet debossed on one side with a 5 and plain on the other side; it is comprised of 5 mg metoclopramide (as 5.91...
Active IngredientMetoclopramide hydrochloride
Dosage FormTablet, orally disintegrating
RouteOral
Strengtheq 5mg base
Market StatusPrescription
CompanySalix Pharms

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Dopamine D2 Receptor Antagonists

Compounds and drugs that bind to and inhibit or block the activation of DOPAMINE D2 RECEPTORS. (See all compounds classified as Dopamine D2 Receptor Antagonists.)


Antiemetics

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


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Dopamine-2 Receptor Antagonist [EPC]; Dopamine D2 Antagonists [MoA]