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M137

Sigma-Aldrich

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
EC Number:
204-950-9
MDL number:
MFCD00083185
UNSPSC Code:
12352200
PubChem Substance ID:
24278129
NACRES:
NA.77

form

solid

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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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

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Certificates of Analysis (COA)

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Abdominal angina as a complication of methysergide maleate therapy.
J Katz et al.
JAMA, 199(2), 124-125 (1967-01-09)
S D Silberstein
Cephalalgia : an international journal of headache, 18(7), 421-435 (1998-10-30)
Methysergide is a semisynthetic ergot alkaloid ergometrine derivative, introduced in pharmacotherapy for migraine prophylaxis as a specific serotonin (5HT) receptor antagonist. Methysergide is not just a 5HT2 antagonist, it is also a 5HT1 agonist. Open and controlled studies attest to
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
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
Jae Il-Han et al.
The Journal of experimental biology, 213(Pt 21), 3603-3614 (2010-10-19)
Serotonergic systems play important roles in modulating stress-induced arousal and vigilance behaviours. The pond snail, Lymnaea, shows multiple defensive vigilance behaviours in response to the stress associated with predator detection. Predator detection elicited by crayfish effluent (CE), increases the time
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