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Merck

M137

Methysergide maleate salt

solid

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Fórmula empírica (notación de Hill):
C21H27N3O2 · C4H4O4
Número CAS:
129-49-7
Peso molecular:
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

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Nombre del producto

Methysergide maleate salt, solid

InChI key

LWYXFDXUMVEZKS-ZVFOLQIPSA-N

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

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

form

solid

color

white to off-white

solubility

DMSO: >10 mg/mL
H2O: 2 mg/mL

originator

Novartis

Quality Level

100

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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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. 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.

Biochem/physiol Actions

Methysergide maleate, also known as sansert, is a semisynthetic ergot alkaloid ergometrine derivative. Methysergide is a serotonin 1(5-HT1) receptor agonist and a nonselective 5-HT2 and 5-HT7 serotonin receptor antagonist. 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.

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

Clase de almacenamiento

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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Certificados de análisis (COA)

Lot/Batch Number
BCCN7273
BCCJ3384
BCCB1072
BCBZ1920
BCBT4806

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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
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
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
E J Mylecharane
Clinical and experimental pharmacology & physiology, 16(6), 517-522 (1989-06-01)
1. The current classification of receptors for 5-hydroxytryptamine (5-HT) is based on functional studies, and encompasses three main receptor types. 2. 5-HT1-like receptors mediate inhibition of release of various neurotransmitters from central and peripheral sites, smooth muscle contraction and relaxation
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