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Chemistry

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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

Methysergide
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 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.)


REF. STANDARDS & IMPURITIES

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ABOUT THIS PAGE

Methysergide Manufacturers

A Methysergide manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Methysergide, including repackagers and relabelers. The FDA regulates Methysergide manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Methysergide API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Methysergide Suppliers

A Methysergide supplier is an individual or a company that provides Methysergide active pharmaceutical ingredient (API) or Methysergide finished formulations upon request. The Methysergide suppliers may include Methysergide API manufacturers, exporters, distributors and traders.

Methysergide GMP

Methysergide Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Methysergide GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Methysergide GMP manufacturer or Methysergide GMP API supplier for your needs.

Methysergide CoA

A Methysergide CoA (Certificate of Analysis) is a formal document that attests to Methysergide's compliance with Methysergide specifications and serves as a tool for batch-level quality control.

Methysergide CoA mostly includes findings from lab analyses of a specific batch. For each Methysergide CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Methysergide may be tested according to a variety of international standards, such as European Pharmacopoeia (Methysergide EP), Methysergide JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Methysergide USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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