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Also known as: 15883-20-2, 2',6'-pipecoloxylidide, Desbutylbupivacaine, Debutylbupivacaine, N-(2,6-dimethylphenyl)-2-piperidinecarboxamide, 2-piperidinecarboxamide, n-(2,6-dimethylphenyl)-
Molecular Formula
C14H20N2O
Molecular Weight
232.32  g/mol
InChI Key
SILRCGDPZGQJOQ-UHFFFAOYSA-N
FDA UNII
NF8RN1V7VM

CAS 15883-20-2
1 2D Structure

CAS 15883-20-2

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
N-(2,6-dimethylphenyl)piperidine-2-carboxamide
2.1.2 InChI
InChI=1S/C14H20N2O/c1-10-6-5-7-11(2)13(10)16-14(17)12-8-3-4-9-15-12/h5-7,12,15H,3-4,8-9H2,1-2H3,(H,16,17)
2.1.3 InChI Key
SILRCGDPZGQJOQ-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC1=C(C(=CC=C1)C)NC(=O)C2CCCCN2
2.2 Other Identifiers
2.2.1 UNII
NF8RN1V7VM
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2',6'-pipecoloxylidide

2. 2',6'-pipecoloxylidide, (+)-isomer

3. 2',6'-pipecoloxylidide, (-)-isomer

4. 2',6'-pipecoloxylidide, (r)-isomer

5. 2',6'-pipecoloxylidide, 14c-labeled

6. 2',6'-pipecoloxylidide, Monoacetate, (r)-isomer

7. Desbutylbupivacaine

8. Pipecolylxylidine-2',6'

2.3.2 Depositor-Supplied Synonyms

1. 15883-20-2

2. 2',6'-pipecoloxylidide

3. Desbutylbupivacaine

4. Debutylbupivacaine

5. N-(2,6-dimethylphenyl)-2-piperidinecarboxamide

6. 2-piperidinecarboxamide, N-(2,6-dimethylphenyl)-

7. N-(2',6'-dimethylphenl)-2-piperidine Carboxamide

8. Demethylmepivacaine

9. N-(2',6'-dimethylphenyl)-2-piperidinecarboxamide

10. N-desbutylbupivacaine

11. 2',6'-pipecolylxylidine

12. N-desbutyl Bupivacaine

13. 2,6-pipecoloxylidide

14. Nf8rn1v7vm

15. Bupivacaine Related Compound B

16. Mfcd01701244

17. (rs)-n-(2,6-dimethylphenyl)piperidine-2-carboxamide

18. Mepivacaine Impurity B

19. Unii-nf8rn1v7vm

20. Brn 0206391

21. Mfcd09038786

22. Piperidine-2-carboxylic Acid 2,6-dimethylanilide

23. 2,6-pipecolylxylidine

24. (s)-n-(2',6'-dimethylphenl)-2-piperidine Carboxamide

25. N-(2,6-dimethylphenl)-2-piperidine Carboxamide

26. 4-22-00-00098 (beilstein Handbook Reference)

27. Schembl3261012

28. Bupivacaine Metabolite Ppx

29. Dtxsid90870436

30. Chebi:173673

31. Bcp22656

32. N-(2,6-dimethylphenyl)pipecolinamide

33. Akos000188838

34. Akos016842269

35. Ac-2123

36. Desbutylbupivacaine, Analytical Standard

37. Ds-0343

38. Fs-2754

39. Sy018608

40. Sy021146

41. Bupivacaine Hydrochloride Impurity B

42. 2',6'-pipecoloxylidide, (+/-)-

43. Am20050057

44. Cs-0038135

45. D4348

46. Ft-0649311

47. Ft-0649312

48. Ft-0666276

49. N-desbutylbupivacaine (n-desmethylmepivacaine)

50. A18251

51. Bupivacaine Related Compound B [usp-rs]

52. 883d202

53. Bupivacaine Hydrochloride Related Compound B

54. N-(2`,6`-dimethylphenyl)-2-piperidinecarboxamide

55. N-(2',6'-dimethylphenyl)-2-piperidine Carboxamide

56. Q-100191

57. N-(2,6-dimethylphenyl)-piperidine-2-carboxylic Amide

58. Q27284841

59. (s)-n-(2,6-dimethylphenyl)-piperidine-2-carboxylic Amide

60. Mepivacaine Hydrochloride Impurity B [ep Impurity]

61. Piperidine-2-carboxylic Acid (2,6-dimethyl-phenyl)-amide

62. (2rs)-n-(2,6-dimethylphenyl)piperidine-2-carboxamide

63. (s)-n-(2',6'-dimethylphenyl)-piperidine-2- Carboxylic Amide

64. 2 Inverted Exclamation Mark ,6 Inverted Exclamation Mark -pipecolylxylidine

65. Mepivacaine Impurity B, European Pharmacopoeia (ep) Reference Standard

66. Bupivacaine Related Compound B, United States Pharmacopeia (usp) Reference Standard

67. (2rs)-n-(2,6-dimethylphenyl)piperidine-2-carboxamide (bupivacaine Related Compound B) (bupivacaine Impurity B), Pharmaceutical Secondary Standard; Certified Reference Material

68. N-(2,6-dimethylphenyl)piperidine-2-carboxamide;n-(2',6'-dimethylphenl)-2-piperidine Carboxamide

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 232.32 g/mol
Molecular Formula C14H20N2O
XLogP32.3
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count2
Exact Mass232.157563266 g/mol
Monoisotopic Mass232.157563266 g/mol
Topological Polar Surface Area41.1 Ų
Heavy Atom Count17
Formal Charge0
Complexity257
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 Metabolism/Metabolites

N-(2,6-Dimethylphenyl)piperidine-2-carboxamide is a known human metabolite of levobupivacaine.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


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