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M137

Methysergide maleate salt

solid

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About This Item

Empirical Formula (Hill Notation):
C21H27N3O2 · C4H4O4
CAS Number:
129-49-7
Molecular Weight:
469.53
NACRES:
NA.77
PubChem Substance ID:
24278129
UNSPSC Code:
12352200
EC Number:
204-950-9
MDL number:
MFCD00083185
Form:
solid
Quality level:
100

Key Documents

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form

solid

Quality Level

100

color

white to off-white

solubility

DMSO: >10 mg/mL, H2O: 2 mg/mL

originator

Novartis

SMILES string

OC(=O)\C=C/C(O)=O.[H][C@@]12Cc3cn(C)c4cccc(C1=C[C@H](CN2C)C(=O)N[C@@H](CC)CO)c34

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

InChI key

LWYXFDXUMVEZKS-ZVFOLQIPSA-N

Gene Information

human ... HTR1A(3350), HTR1B(3351), HTR1D(3352), HTR1E(3354), HTR1F(3355), HTR2A(3356), HTR2B(3357), HTR2C(3358), HTR7(3363)

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1 of 4

This Item
U115T123C231
Methysergide maleate salt solid

Sigma-Aldrich

M137

Methysergide maleate salt

U-101958 maleate salt solid

Sigma-Aldrich

U115

U-101958 maleate salt

Thioperamide maleate salt solid

Sigma-Aldrich

T123

Thioperamide maleate salt

CGP-20712A methanesulfonate salt solid, ≥98% (HPLC)

Sigma-Aldrich

C231

CGP-20712A methanesulfonate salt

form

solid

form

solid

form

solid

form

solid

Quality Level

100

Quality Level

100

Quality Level

-

Quality Level

100

solubility

DMSO: >10 mg/mL, H2O: 2 mg/mL

solubility

DMSO: 11 mg/mL, ethanol: 2.7 mg/mL, H2O: 3 mg/mL

solubility

H2O: >10 mg/mL, DMSO: 12 mg/mL, ethanol: 3 mg/mL

solubility

H2O: >10 mg/mL, DMSO: 100 mg/mL

color

white to off-white

color

off-white

color

white

color

white to off-white

originator

Novartis

originator

-

originator

-

originator

-

Gene Information

human ... HTR1A(3350), HTR1B(3351), HTR1D(3352), HTR1E(3354), HTR1F(3355), HTR2A(3356), HTR2B(3357), HTR2C(3358), HTR7(3363)

Gene Information

human ... DRD4(1815)

Gene Information

human ... HRH3(11255)

Gene Information

human ... ADRB1(153)

Application

Methysergide maleate salt has been used as a serotonin (5HT) receptor antagonist to evaluate the potential systemic effects of methysergide (METH) and 5-HT infusions on production and milk composition in multiparous Holstein cows.[1] It may also be used as a serotonin receptor blocker to identify the serotonergic receptor type involved in the direct excitation of mitral cells in the main olfactory bulb.[2]

Biochem/physiol Actions

Methysergide maleate, also known as sansert,[3] is a semisynthetic ergot alkaloid ergometrine derivative.[4] Methysergide is a serotonin 1(5-HT1) receptor agonist and a nonselective 5-HT2 and 5-HT7 serotonin receptor antagonist.[1][2] Methysergide maleate is used as a pharmacological agent to treat migraines and other vascular headaches. But, prolonged and uncontrolled use of this drug may cause Leriche′s syndrome, angina pectoris, acute ischemia of the limbs. In addition, gastrointestinal side effects, such as abdominal cramps, nausea, and diarrhea have also been observed in few patients.[5]

Features and Benefits

This compound was developed by Novartis. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN7273
BCCJ3384
BCCB1072
BCBZ1920
BCBT4806

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Seth D Depuy et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 31(6), 1981-1990 (2011-02-11)
We used optogenetics to determine the global respiratory effects produced by selectively stimulating raphe obscurus (RO) serotonergic neurons in anesthetized mice and to test whether these neurons detect changes in the partial pressure of CO(2), and hence function as central
Julien Bacqué-Cazenave et al.
Scientific reports, 7, 39935-39935 (2017-01-04)
Social interactions leading to dominance hierarchies often elicit psychological disorders in mammals including harassment and anxiety. Here, we demonstrate that this sequence also occurs in an invertebrate, the crayfish Procambarus clarkii. When placed in the restricted space of an aquarium
J A Terrón
British journal of pharmacology, 121(3), 563-571 (1997-06-01)
1. The receptor mediating the long-lasting hypotensive effect of intravenous (i.v.) 5-hydroxytryptamine (5-HT) in the rat was originally classified as 5-HT1-like. Since some pharmacological properties of this receptor are closely similar to those for the cloned 5-ht7 receptor, the present
Acute ischemia of a limb complicating methysergide maleate therapy.
A L URELES et al.
JAMA, 183, 1041-1042 (1963-03-23)
N H Prins et al.
British journal of pharmacology, 127(6), 1431-1437 (1999-08-24)
This study aimed to characterize for the first time in vitro 5-HT4 receptors in the canine gastrointestinal tract. For this purpose, we used circular muscle strips of the canine isolated rectum. In the presence of methysergide (60 microM), 5-HT induced
View All Related Papers

Global Trade Item Number

SKUGTIN
M137-50MG04061832091839
M137-10MG04061834038160
M137-2MG04061834038177

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