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Citanest

Synopsis, Chemistry

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Also known as: 1786-81-8, Propitocaine hydrochloride, Prilocaine hcl, Xylonest, Citanest hydrochloride, Citanest plain

Molecular Formula

C₁₃H₂₁ClN₂O

Molecular Weight

256.77 g/mol

InChI Key

BJPJNTKRKALCPP-UHFFFAOYSA-N

FDA UNII

MJW015BAPH

A local anesthetic that is similar pharmacologically to LIDOCAINE. Currently, it is used most often for infiltration anesthesia in dentistry.

1 2D Structure

Citanest

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-(2-methylphenyl)-2-(propylamino)propanamide;hydrochloride

2.1.2 InChI

InChI=1S/C13H20N2O.ClH/c1-4-9-14-11(3)13(16)15-12-8-6-5-7-10(12)2;/h5-8,11,14H,4,9H2,1-3H3,(H,15,16);1H

2.1.3 InChI Key

BJPJNTKRKALCPP-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCCNC(C)C(=O)NC1=CC=CC=C1C.Cl

2.2 Other Identifiers

2.2.1 UNII

MJW015BAPH

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Citanest

2. Citanest Octapressin

3. Prilocaine

4. Propitocaine

5. Xylonest

2.3.2 Depositor-Supplied Synonyms

1. 1786-81-8

2. Propitocaine Hydrochloride

3. Prilocaine Hcl

4. Xylonest

5. Citanest Hydrochloride

6. Citanest Plain

7. Prilocaine (hydrochloride)

8. Prilocaine, Hcl

9. Astra 1512

10. N-(2-methylphenyl)-2-(propylamino)propanamide Hydrochloride

11. Mfcd00079279

12. 2-(propylamino)-

13. 878791-35-6

14. L-67

15. N-(2-methylphenyl)-2-(propylamino)propanamide;hydrochloride

16. Mjw015baph

17. 2-(propylamino)-m-propionotoluidide Hydrochloride

18. 2-(propylamino)-o-propionotoluidide Hydrochloride

19. Nsc-758432

20. Mls000069690

21. Propanamide, N-(2-methylphenyl)-2-(propylamino)-, Monohydrochloride

22. Prilocaine Chloride

23. Smr000058506

24. Propanamide, N-(2-methylphenyl)-2-(propylamino)-, Hydrochloride (1:1)

25. 2-(propylamino)-o-propionotoluidide Monohydrochloride

26. Alpha-propylamine-2-methyl-propionanilide Hydrochloride

27. Dsstox_cid_11956

28. Dsstox_rid_78897

29. Dsstox_gsid_31956

30. Propitocaine Hydrochloride (jan)

31. Propitocaine Hydrochloride [jan]

32. Chebi:32053

33. Prilocaine Hydrochloride [usan]

34. Sr-01000076094

35. Einecs 217-244-0

36. Unii-mjw015baph

37. 2-(propylamino)-n-(o-tolyl)propanamide Hydrochloride

38. Citanest (tn)

39. Prestwick_616

40. Prilocaine Hydrochloride [usan:usp]

41. O-propionotoluidide, 2-(propylamino)-, Monohydrochloride

42. Propitocainehydrochloride

43. Opera_id_480

44. Ncgc00016594-01

45. Cas-1786-81-8

46. L-67 Hydrochloride

47. Dl-(+-)-prilocaine Hcl

48. Mls002222230

49. Mls002548864

50. Schembl330180

51. Spectrum1503270

52. 2-(propylamino)-n-(o-tolyl)propionamide Hydrochloride

53. Amy587

54. Prilocaine Hydrochloride (usp)

55. Chembl1200586

56. Dtxsid2031956

57. Niosh/tx1480000

58. Hy-b0137a

59. Dl-(+-)-prilocaine Hydrochloride

60. Hms1568h19

61. Hms1922o15

62. Pharmakon1600-01503270

63. Prilocaine Hcl (propitocaine Hcl)

64. Act04757

65. Bcp22337

66. Ex-a2857

67. Tox21_110513

68. Tox21_501005

69. Ccg-39327

70. Nsc758432

71. Prilocaine Hydrochloride [mi]

72. S5482

73. Akos015895106

74. Tox21_110513_1

75. Ac-2099

76. Cs-1930

77. Ks-5024

78. Lp01005

79. Nc00474

80. Nsc 758432

81. Prilocaine Hydrochloride [mart.]

82. Prilocaine Hydrochloride [vandf]

83. Ncgc00015860-06

84. Ncgc00094299-01

85. Ncgc00094299-02

86. Ncgc00094299-03

87. Ncgc00094299-04

88. Ncgc00094299-05

89. Ncgc00261690-01

90. Prilocaine Hydrochloride [usp-rs]

91. Prilocaine Hydrochloride [who-dd]

92. Bp166249

93. Prilocaine Hydrochloride, >=98% (tlc)

94. Sy066795

95. Bcp0726000006

96. Eu-0101005

97. Ft-0633840

98. P2038

99. Tx14800000

100. Prilocaine Hydrochloride [ep Impurity]

101. Prilocaine Hydrochloride [orange Book]

102. D01243

103. P 9547

104. Prilocaine Hydrochloride [ep Monograph]

105. Prilocaine Hydrochloride [usp Monograph]

106. 2-(propylamino)-n-o-tolylpropanamide Hydrochloride

107. 786p818

108. A812391

109. Q-201619

110. Sr-01000076094-1

111. Sr-01000076094-6

112. N-(2-methylphenyl)-n2-propylalaninamide Hydrochloride

113. Q27114764

114. Prilocaine Hydrochloride, Meets Usp Testing Specifications

115. O-propionotoluidide, 2-(propylamino)-, Hydrochloride, (+-)-

116. (+-)-n-(2-methylphenyl)-2-(propylamino)propanamide Hydrochloride

117. N-(2-methylphenyl)-2-(propylamino)propanamide Hydrochloride (1:1)

118. Prilocaine Hydrochloride, European Pharmacopoeia (ep) Reference Standard

119. Propanamide, N-(2-methylphenyl)-2-(propylamino)-, Hydrochloride, (+-)-

120. Prilocaine For Peak Identification, European Pharmacopoeia (ep) Reference Standard

121. Prilocaine Hydrochloride, United States Pharmacopeia (usp) Reference Standard

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₃H₂₁ClN₂O
Molecular Weight	256.77 g/mol
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	5
Exact Mass	256.1342410 g/mol
Monoisotopic Mass	256.1342410 g/mol
Topological Polar Surface Area	41.1 Å²
Heavy Atom Count	17
Formal Charge	0
Complexity	218
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Prilocaine hydrochloride
Drug Label	Prilocaine Hydrochloride Injection, USP, 4% is a sterile, non pyrogenic isotonic solution that contains a local anesthetic agent and is administered parenterally by injection. See INDICATIONS AND USAGE for specific uses. The quantitative composition...
Active Ingredient	Prilocaine hydrochloride
Dosage Form	Injectable
Route	Injection
Strength	4%
Market Status	Prescription
Company	Septodont

2 of 2
Drug Name	Prilocaine hydrochloride
Drug Label	Prilocaine Hydrochloride Injection, USP, 4% is a sterile, non pyrogenic isotonic solution that contains a local anesthetic agent and is administered parenterally by injection. See INDICATIONS AND USAGE for specific uses. The quantitative composition...
Active Ingredient	Prilocaine hydrochloride
Dosage Form	Injectable
Route	Injection
Strength	4%
Market Status	Prescription
Company	Septodont

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]