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    Lobeline Hydrochloride

    ACTIVE PHARMA INGREDIENTS

    PharmaCompass
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    2D Structure
    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

    2D Structure

    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 Weight 373.9 g/mol
    Molecular Formula C22H28ClNO2
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count6
    Exact Mass373.1808568 g/mol
    Monoisotopic Mass373.1808568 g/mol
    Topological Polar Surface Area40.5 Ų
    Heavy Atom Count26
    Formal Charge0
    Complexity412
    Isotope Atom Count0
    Defined Atom Stereocenter Count3
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    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