Methysergide

Synopsis, Chemistry

DOSSIERs // Finished Dosage Formulations

1 Dossiers, 1 FDA Orange Book

ANALYTICAL SOLUTION(s)

1 USP Standards, 1 Other Ref. Standards

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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

Methysergide

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 Formula	C₂₅H₃₁N₃O₆
Molecular Weight	469.5 g/mol
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	6
Exact Mass	469.22128572 g/mol
Monoisotopic Mass	469.22128572 g/mol
Topological Polar Surface Area	132 Å²
Heavy Atom Count	34
Formal Charge	0
Complexity	697
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

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.)