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ACTIVE PHARMA INGREDIENTS

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Chemistry

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Also known as: Lobeline hcl, 134-63-4, Alpha-lobeline hydrochloride, (-)-lobeline hydrochloride, L-lobeline hydrochloride, Lobeline (hydrochloride)

Molecular Formula

C₂₂H₂₈ClNO₂

Molecular Weight

373.9 g/mol

InChI Key

MKMYPTLXLWOUSO-NFQNBQCWSA-N

FDA UNII

96J834CB88

1 2D Structure

Lobeline Hydrochloride

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[(2R,6S)-6-[(2S)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanone;hydrochloride

2.1.2 InChI

InChI=1S/C22H27NO2.ClH/c1-23-19(15-21(24)17-9-4-2-5-10-17)13-8-14-20(23)16-22(25)18-11-6-3-7-12-18;/h2-7,9-12,19-21,24H,8,13-16H2,1H3;1H/t19-,20+,21-;/m0./s1

2.1.3 InChI Key

MKMYPTLXLWOUSO-NFQNBQCWSA-N

2.1.4 Canonical SMILES

CN1C(CCCC1CC(=O)C2=CC=CC=C2)CC(C3=CC=CC=C3)O.Cl

2.1.5 Isomeric SMILES

CN1[C@@H](CCC[C@@H]1CC(=O)C2=CC=CC=C2)C[C@@H](C3=CC=CC=C3)O.Cl

2.2 Other Identifiers

2.2.1 UNII

96J834CB88

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. Lobeline Hcl

2. 134-63-4

3. Alpha-lobeline Hydrochloride

4. (-)-lobeline Hydrochloride

5. L-lobeline Hydrochloride

6. Lobeline (hydrochloride)

7. Lobeline Hydrochloride [jan]

8. Zoolobelin

9. Mls000069392

10. Lobron

11. 96j834cb88

12. Smr000058465

13. Alpha-lobeline Hcl

14. 2-[(2r,6s)-6-[(2s)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanone Hydrochloride

15. Lobeline Hydrochloride (jan)

16. Lobelin Hydrochlorde

17. Lobelin Hydrochloride

18. Lobelini Hydrochloridum

19. Lobelinum Hydrochloricum

20. Sr-01000000002

21. Lobeline Alpha (-) Hydrochoride

22. Sr-01000075960

23. Unii-96j834cb88

24. (-)-alpha-lobeline Hydrochloride

25. Einecs 205-150-2

26. A-lobeline Hydrochloride

27. Opera_id_410

28. Nsc-757421 Hydrochloride

29. Inflatine Hydrochloride

30. Mls000758290

31. Mls001148112

32. Mls001424136

33. Schembl467021

34. Chembl1257005

35. Dtxsid10928382

36. Hms1569f12

37. (-)-lobeline Hydrochloride, 98%

38. Lobeline Hydrochloride [mi]

39. 2-((2r,6s)-6-((s)-2-hydroxy-2-phenylethyl)-1-methylpiperidin-2-yl)-1-phenylethan-1-one Hydrochloride

40. Act06730

41. Ex-a1345

42. Hy-b0979

43. Tox21_500698

44. S3972

45. .alpha.-lobeline Hydrochloride

46. Akos024282588

47. Lobeline Hydrochloride [mart.]

48. Am62794

49. Ccg-101032

50. Cs-4469

51. Lobeline Hydrochloride [who-dd]

52. Lp00698

53. Nc00282

54. Acetophenone, 2-(6-(beta-hydroxyphenethyl)-1-methyl-2-piperidyl)-, Hydrochloride, (-)-

55. Ncgc00094052-01

56. Ncgc00261383-01

57. As-48029

58. Eu-0100698

59. Lobeline Hydrochloride [ep Monograph]

60. D02202

61. F17567

62. L 4376

63. Sr-01000000002-2

64. Sr-01000000002-5

65. Sr-01000075960-1

66. Q27271904

67. Lobeline Hydrochloride, European Pharmacopoeia (ep) Reference Standard

68. 2-(6-(.beta.-hydroxyphenethyl)-1-methyl-2-piperidyl)acetophenone Hydrochloride

69. 2-[(2r,6s)-6-[(2s)-2-hydroxyphenethyl)]-1-methyl-2-piperidinyl]acetophenone Hydrochloride

70. 2-[6-(2-hydroxy-2-phenethyl)-1-methyl-2-piperidyl]acetophenone Hydrochloride

71. 2-((2r,6s)-6-((2s)-2-hydroxy-2-phenylethyl)-1-methyl-2-piperidinyl)-1-phenylethanone Hydrochloride

72. 2-((2r,6s)-6-((s)-2-hydroxy-2-phenylethyl)-1-methylpiperidin-2-yl)-1-phenylethan-1-onehydrochloride

73. 2-((2r,6s)-6-((s)-2-hydroxy-2-phenylethyl)-1-methylpiperidin-2-yl)-1-phenylethanone Hydrochloride

74. 2-[(2r,6s)-6-[(2s)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanone;hydrochloride

75. Ethanone, 2-((2r,6s)-6-((2s)-2-hydroxy-2-phenylethyl)-1-methyl-2-piperidinyl)-1-phenyl-, Hydrochloride

76. Ethanone, 2-(6-(2-hydroxy-2-phenylethyl)-1-methyl-2-piperidinyl)-1-phenyl-, Hydrochloride, (2r-(2alpha,6alpha(s*))-

77. Ethanone, 2-[(2r,6s)-6-[(2s)-2-hydroxy-2-phenylethyl]-1-methyl-2-piperidinyl]-1-phenyl-, Hydrochloride (1:1)

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₂₈ClNO₂
Molecular Weight	373.9 g/mol
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	6
Exact Mass	373.1808568 g/mol
Monoisotopic Mass	373.1808568 g/mol
Topological Polar Surface Area	40.5 Å²
Heavy Atom Count	26
Formal Charge	0
Complexity	412
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Therapeutic Uses

HAS BEEN USED AS A RESPIRATORY STIMULANT; ALSO FOR TREATING TOBACCO ADDICTION. THE WATER-SOL HYDROCHLORIDE & SULFATE HAVE BEEN ADMIN BY PARENTERAL ROUTES.

Osol, A. (ed.). Remington's Pharmaceutical Sciences. 16th ed. Easton, Pennsylvania: Mack Publishing Co., 1980., p. 808

(VET) HAS BEEN USED AS A RESPIRATORY STIMULANT, RUMINATORIC /LOBELINE/

Budavari, S. (ed.). The Merck Index - Encyclopedia of Chemicals, Drugs and Biologicals. Rahway, NJ: Merck and Co., Inc., 1989., p. 873

5 Pharmacology and Biochemistry

5.1 Mechanism of Action

TWO NATURAL ALKALOIDS, NICOTINE & LOBELINE, OWE MUCH OF THEIR PHARMACOLOGICAL ACTIVITY TO THEIR ACTIONS AT AUTONOMIC GANGLIA. ... LOBELINE HAS MANY OF THE SAME ACTIONS IN THE BODY AS NICOTINE BUT IS LESS POTENT. /LOBELINE/

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 180

... Lobeline ... resembles nicotine and coniine in its action, causing first stimulation then paralysis of autonomic ganglia. /Lobeline/

Humphreys, D.J. Veterinary Toxicology. 3rd ed. London, England: Bailliere Tindell, 1988., p. 245

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