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    Methysergide

    FINISHED DOSAGE FORMULATIONS

    REF. STANDARDS & IMPURITIES

    PharmaCompass
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    2D Structure
    Also known as: 129-49-7, Methysergide maleate salt, Methysergide hydrogen maleate, Deseril-retard, Desernil bismaleate, Methysergide maleate [usp]
    Molecular Formula
    C25H31N3O6
    Molecular Weight
    469.5  g/mol
    InChI Key
    LWYXFDXUMVEZKS-ZVFOLQIPSA-N
    FDA UNII
    2U7H1466GH
    An ergot derivative that is a congener of LYSERGIC ACID DIETHYLAMIDE. It antagonizes the effects of serotonin in blood vessels and gastrointestinal smooth muscle, but has few of the properties of other ergot alkaloids. Methysergide is used prophylactically in migraine and other vascular headaches and to antagonize serotonin in the carcinoid syndrome.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (6aR,9R)-N-[(2S)-1-hydroxybutan-2-yl]-4,7-dimethyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide;(Z)-but-2-enedioic acid
    2.1.2 InChI
    InChI=1S/C21H27N3O2.C4H4O4/c1-4-15(12-25)22-21(26)14-8-17-16-6-5-7-18-20(16)13(10-23(18)2)9-19(17)24(3)11-14;5-3(6)1-2-4(7)8/h5-8,10,14-15,19,25H,4,9,11-12H2,1-3H3,(H,22,26);1-2H,(H,5,6)(H,7,8)/b;2-1-/t14-,15+,19-;/m1./s1
    2.1.3 InChI Key
    LWYXFDXUMVEZKS-ZVFOLQIPSA-N
    2.1.4 Canonical SMILES
    CCC(CO)NC(=O)C1CN(C2CC3=CN(C4=CC=CC(=C34)C2=C1)C)C.C(=CC(=O)O)C(=O)O
    2.1.5 Isomeric SMILES
    CC[C@@H](CO)NC(=O)[C@H]1CN([C@@H]2CC3=CN(C4=CC=CC(=C34)C2=C1)C)C.C(=C\C(=O)O)\C(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    2U7H1466GH
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Dsernil Sandoz

    2. Dsernil-sandoz

    3. Deseril

    4. Desril

    5. Dimaleate, Methysergide

    6. Dimethylergometrin

    7. Maleate, Methysergide

    8. Methylmethylergonovine

    9. Methysergide

    10. Methysergide Dimaleate

    11. Sansert

    12. Uml 491

    13. Uml-491

    14. Uml491

    2.3.2 Depositor-Supplied Synonyms

    1. 129-49-7

    2. Methysergide Maleate Salt

    3. Methysergide Hydrogen Maleate

    4. Deseril-retard

    5. Desernil Bismaleate

    6. Methysergide Maleate [usp]

    7. 129-49-7 (maleate)

    8. 2u7h1466gh

    9. Nsc-759143

    10. Methysergide Maleate (usp)

    11. Methysergide Bimaleate

    12. 1-methyl-d-lysergic Acid Butanolamide Dimaleate

    13. Mls000069364

    14. (6ar,9r)-n-[(2s)-1-hydroxybutan-2-yl]-4,7-dimethyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide; Maleate (1:1)

    15. Ergoline-8-carboxamide,9,10-didehydro-n-[(1s)-1-(hydroxymethyl)propyl]-1,6-dimethyl-, (8b)-,(2z)-2-butenedioate (1:1) (salt)

    16. Smr000058483

    17. Einecs 204-950-9

    18. Nsc 186061

    19. Unii-2u7h1466gh

    20. Sansert (tn)

    21. Lysergamide, N-((1-hydroxymethyl)propyl)-1-methyl-, Maleate

    22. Methysergidemaleate

    23. Regid855989

    24. (+)-n-((1-hydroxymethyl)propyl)-1-methyl-d-lysergamide Bimaleate

    25. (6ar,9r)-n-[(2s)-1-hydroxybutan-2-yl]-4,7-dimethyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide;(z)-but-2-enedioic Acid

    26. 1-(hydroxymethyl)propylamide Of 1-methyl-(+)-lysergic Acid Hydrogen Maleate

    27. 9,10-didehydro-n-(1-(hydroxymethyl)propyl)-1,6-dimethylergoline-8beta-carboxamide Maleate (1:1) (salt)

    28. Mls001076153

    29. Chebi:6894

    30. Chembl1200938

    31. Methysergide Maleate Salt, Solid

    32. Schembl21803661

    33. Dtxsid901017106

    34. Hms2093n13

    35. Hms2231l15

    36. Hms3262n07

    37. Hms3414j11

    38. Hms3678j09

    39. Hms3887o05

    40. Pharmakon1600-01505492

    41. Methysergide Maleate Assay Standard

    42. Methysergide Maleate [vandf]

    43. Tox21_500863

    44. Methysergide Maleate [mart.]

    45. Nsc759143

    46. Methysergide Maleate [usp-rs]

    47. Methysergide Maleate [who-dd]

    48. Akos024456362

    49. Ccg-213467

    50. Lp00863

    51. Ncgc00261548-01

    52. Ergoline-8-beta-carboxamide, 9,10-didehydro-n-(1-(hydroxymethyl)propyl)-1,6-dimethyl-, Maleate (1:1) (salt)

    53. Ergoline-8-carboxamide, 9,10-didehydro-n-((1s)-1-(hydroxymethyl)propyl)-1,6-dimethyl-, (8beta)-, (2z)-2-butenedioate (1:1) (salt)

    54. Ergoline-8-carboxamide, 9,10-didehydro-n-(1-(hydroxymethyl)propyl)-1,6-dimethyl-, (8beta)-, (z)-2-butenedioate (1:1) (salt)

    55. Ergoline-8beta-carboxamide, 9,10-didehydro-n-(1-(hydroxymethyl)propyl)-1,6-dimethyl-, Maleate (1:2) (salt)

    56. Methysergide Hydrogen Maleate [mi]

    57. Methysergide Maleate [orange Book]

    58. Smr000653472

    59. Methysergide Maleate [usp Impurity]

    60. Methysergide Maleate [usp Monograph]

    61. Eu-0100863

    62. M-137

    63. D00681

    64. Sr-01000002986

    65. Sr-01000002986-2

    66. Q27255601

    67. Methysergide Maleate, United States Pharmacopeia (usp) Reference Standard

    68. [8?(s)]-9,10-didehydro-n-[1-(hydroxymethyl)propyl]-1,6-dimethylergoline-8-carboxamide Maleate

    69. 9,10-didehydro-n-(1-(hydroxymethyl)propyl)-1,6-dimethylergoline-8.beta.-carboxamide Maleate (1:1) (salt)

    70. Ergoline-8-carboxamide, 9,10-didehydro-n-(1-(hydroxymethyl)propyl)-1,6-dimethyl-, (8.beta.)-, (z)-2-butenedioate (1:1) (salt)

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 469.5 g/mol
    Molecular Formula C25H31N3O6
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count6
    Exact Mass469.22128572 g/mol
    Monoisotopic Mass469.22128572 g/mol
    Topological Polar Surface Area132 Ų
    Heavy Atom Count34
    Formal Charge0
    Complexity697
    Isotope Atom Count0
    Defined Atom Stereocenter Count3
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Serotonin Antagonists

    Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or SEROTONIN RECEPTOR AGONISTS. (See all compounds classified as Serotonin Antagonists.)

    Vasoconstrictor Agents

    Drugs used to cause constriction of the blood vessels. (See all compounds classified as Vasoconstrictor Agents.)