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2D Structure
Also known as: 1722-62-9, Mepivacaine hcl, Scandicain, N-(2,6-dimethylphenyl)-1-methylpiperidine-2-carboxamide hydrochloride, Optocain, Scandonest plain
Molecular Formula
C15H23ClN2O
Molecular Weight
282.81  g/mol
InChI Key
RETIMRUQNCDCQB-UHFFFAOYSA-N
FDA UNII
4VFX2L7EM5

A local anesthetic that is chemically related to BUPIVACAINE but pharmacologically related to LIDOCAINE. It is indicated for infiltration, nerve block, and epidural anesthesia. Mepivacaine is effective topically only in large doses and therefore should not be used by this route. (From AMA Drug Evaluations, 1994, p168)
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
N-(2,6-dimethylphenyl)-1-methylpiperidine-2-carboxamide;hydrochloride
2.1.2 InChI
InChI=1S/C15H22N2O.ClH/c1-11-7-6-8-12(2)14(11)16-15(18)13-9-4-5-10-17(13)3;/h6-8,13H,4-5,9-10H2,1-3H3,(H,16,18);1H
2.1.3 InChI Key
RETIMRUQNCDCQB-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC1=C(C(=CC=C1)C)NC(=O)C2CCCCN2C.Cl
2.2 Other Identifiers
2.2.1 UNII
4VFX2L7EM5
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Carbocane

2. Carbocaine

3. Isocaine

4. Isogaine

5. Meaverin

6. Mecain

7. Mepihexal

8. Mepivacain Injektopas

9. Mepivacain-injektopas

10. Mepivacaina Braun

11. Mepivacaine

12. Mepivacaine Monohydrochloride

13. Mepivastesin

14. Polocaine

15. Scandicain

16. Scandicaine

17. Scandinibsa

18. Scandonest

2.3.2 Depositor-Supplied Synonyms

1. 1722-62-9

2. Mepivacaine Hcl

3. Scandicain

4. N-(2,6-dimethylphenyl)-1-methylpiperidine-2-carboxamide Hydrochloride

5. Optocain

6. Scandonest Plain

7. Carbocain

8. Mepivacaine (hydrochloride)

9. Polocaine-mpf

10. Arestocaine Hydrochloride

11. N-(2,6-dimethylphenyl)-1-methyl-2-piperidinecarboxamide Hydrochloride

12. Mepivacaine Monohydrochloride

13. Isocaine Hydrochloride

14. 1-methyl-2',6'-pipecoloxylidide Hydrochloride

15. 1-methyl-2',6'-pipecoloxylidide Monohydrochloride

16. Mepivicaine Hydrochloride

17. Nsc-758674

18. N-(2,6-dimethylphenyl)-1-methylpiperidine-2-carboxamide;hydrochloride

19. 4vfx2l7em5

20. (1-methyl-dl-piperidine-2-carboxylic Acid)-2,6-dimethylanilide Hydrochloride

21. 1722-62-9 (hcl)

22. (+-)-1-methyl-2',6'-pipecoloxylidide Monohydrochloride

23. Mls000028662

24. Chebi:6760

25. Carbocaina

26. Mepivastesin

27. Scandonest

28. Meaverin

29. (+/-)-mepivacaine Hydrochloride

30. Ncgc00095108-01

31. Scandinibsa

32. Chlorocain

33. Smr000058904

34. Sabol

35. 2-piperidinecarboxamide, N-(2,6-dimethylphenyl)-1-methyl-, Hydrochloride (1:1)

36. N-(2,6-dimethylphenyl)-1-methylpiperidine-2-carboxamide Hydrochloride (1:1)

37. Carbocaine Hydrochloride

38. Mepivacaine Chlorhydrate

39. Einecs 217-023-9

40. Mfcd00144738

41. Carbocaine Monohydrochloride

42. Unii-4vfx2l7em5

43. Sr-01000000263

44. Mepivacaine Hydrochloride [jan]

45. 1-methyl-2',6'-pipecoloxylidine Hydrochloride

46. Carbocaine (tn)

47. Polocaine (tn)

48. Mepivacaine Hydrochloride [usp:jan]

49. Mepivacain Hydrochloride

50. Scandonest Plain (tn)

51. Opera_id_1165

52. Dsstox_cid_11566

53. Dsstox_rid_78885

54. Dsstox_gsid_31566

55. Schembl34245

56. Mls001074068

57. Mls001424226

58. Spectrum1504148

59. Amy523

60. 2',6'-pipecoloxylidide, 1-methyl -, Monohydrochloride

61. Chembl1200440

62. Dtxsid4031566

63. Hy-b0517a

64. Hms1922d17

65. Pharmakon1600-01504148

66. Act02686

67. Bcp21546

68. Tox21_111424

69. Ccg-39081

70. Nsc758674

71. S3155

72. Mepivacaine Hydrochloride [mi]

73. Akos015889311

74. Mepivacaine Hydrochloride (jp17/usp)

75. Ac-2102

76. Ccg-101083

77. Ks-1271

78. Nc00333

79. Nsc 758674

80. 2-piperidinecarboxamide, N-(2,6-dimethylphenyl)-1-methyl-, Monohydrochloride, (+-)-

81. Mepivacaine Hydrochloride [mart.]

82. Mepivacaine Hydrochloride [vandf]

83. Ncgc00095108-02

84. Ncgc00095108-03

85. Bm162010

86. Mepivacaine Hydrochloride [usp-rs]

87. Mepivacaine Hydrochloride [who-dd]

88. Cas-1722-62-9

89. Ft-0601566

90. Ft-0671021

91. Ft-0671022

92. M2560

93. Sw197713-3

94. Mepivacaine Hydrochloride [green Book]

95. A12146

96. D00738

97. Mepivacaine Hydrochloride [ep Monograph]

98. Mepivacaine Hydrochloride [orange Book]

99. Mepivacaine Hydrochloride [usp Impurity]

100. Mepivacaine Hydrochloride [usp Monograph]

101. 722m629

102. A811391

103. (+/-)-mepivacaine Hydrochloride, >=98% (hplc)

104. Q-201354

105. Sr-01000000263-4

106. Q27107324

107. (+/-)-1-methyl-2',6'-pipecoloxylidide Monohydrochloride

108. N-(2,6-dimethylphenyl)-1-methylpiperidine-2-carboxamide Hcl

109. Mepivacaine Hydrochloride, 98.0-102.0%, Meets Usp Testing Specifications

110. Mepivacaine Hydrochloride, European Pharmacopoeia (ep) Reference Standard

111. Mepivacaine Hydrochloride, Pharmaceutical Secondary Standard; Certified Reference Material

112. Mepivacaine Hydrochloride, United States Pharmacopeia (usp) Reference Standard

113. 2-piperidinecarboxamide, N-(2,6-dimethylphenyl)-1-methyl-, Monohydrochloride, (+/-)-

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 282.81 g/mol
Molecular Formula C15H23ClN2O
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count2
Exact Mass282.1498911 g/mol
Monoisotopic Mass282.1498911 g/mol
Topological Polar Surface Area32.3 Ų
Heavy Atom Count19
Formal Charge0
Complexity282
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 6  
Drug NameIsocaine hydrochloride
Active IngredientMepivacaine hydrochloride
Dosage FormInjectable
RouteInjection
Strength3%
Market StatusPrescription
CompanyNovocol

2 of 6  
Drug NameMepivacaine hydrochloride
Drug LabelMepivacaine hydrochloride is 2-Piperidinecarboxamide, N-(2,6-dimethylphenyl)-1-methyl-, monohydrochloride and has the following structural formula:The molecular formula is C15H22N2O HCl. It is a white, crystalline odorless powder, soluble in water, b...
Active IngredientMepivacaine hydrochloride
Dosage FormInjectable
RouteInjection
Strength3%
Market StatusPrescription
CompanyHospira

3 of 6  
Drug NameScandonest plain
Drug LabelMepivacaine hydrochloride, a tertiary amide used as a local anesthetic, is 1-methyl-2', 6'-pipecoloxylidide monohydrochloride with the following structural formula :C15 H22 N2O. HCL...
Active IngredientMepivacaine hydrochloride
Dosage FormInjectable
RouteInjection
Strength3%
Market StatusPrescription
CompanyDeproco

4 of 6  
Drug NameIsocaine hydrochloride
Active IngredientMepivacaine hydrochloride
Dosage FormInjectable
RouteInjection
Strength3%
Market StatusPrescription
CompanyNovocol

5 of 6  
Drug NameMepivacaine hydrochloride
Drug LabelMepivacaine hydrochloride is 2-Piperidinecarboxamide, N-(2,6-dimethylphenyl)-1-methyl-, monohydrochloride and has the following structural formula:The molecular formula is C15H22N2O HCl. It is a white, crystalline odorless powder, soluble in water, b...
Active IngredientMepivacaine hydrochloride
Dosage FormInjectable
RouteInjection
Strength3%
Market StatusPrescription
CompanyHospira

6 of 6  
Drug NameScandonest plain
Drug LabelMepivacaine hydrochloride, a tertiary amide used as a local anesthetic, is 1-methyl-2', 6'-pipecoloxylidide monohydrochloride with the following structural formula :C15 H22 N2O. HCL...
Active IngredientMepivacaine hydrochloride
Dosage FormInjectable
RouteInjection
Strength3%
Market StatusPrescription
CompanyDeproco

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Anesthetics, Local

Drugs that block nerve conduction when applied locally to nerve tissue in appropriate concentrations. They act on any part of the nervous system and on every type of nerve fiber. In contact with a nerve trunk, these anesthetics can cause both sensory and motor paralysis in the innervated area. Their action is completely reversible. (From Gilman AG, et. al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed) Nearly all local anesthetics act by reducing the tendency of voltage-dependent sodium channels to activate. (See all compounds classified as Anesthetics, Local.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Amides [CS]; Local Anesthesia [PE]; Amide Local Anesthetic [EPC]