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Merck

5.06419

Methysergide Maleate

Synonym(s):

Methysergide Maleate, 5-HT Serotonin Receptor Antagonsit, Methysergide Maleate, UML-491

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About This Item

Empirical Formula (Hill Notation):
C21H27N3O2 · xC4H4O4
CAS Number:
129-49-7
Molecular Weight:
353.46 (free base basis)
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD00083185

Key Documents

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SMILES string

[n]1(c2c3c(c1)C[C@H]4N(C[C@@H](C=C4c3ccc2)C(=O)N[C@H](CO)CC)C)C.OC(=O)\C=C/C(=O)O

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

assay

≥99% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

off-white

solubility

water: 10 mM

storage temp.

2-8°C

Quality Level

100

Biochem/physiol Actions

Primary Target
5-HT

Disclaimer

Toxicity: Toxic (F)

General description

An antagonist of the 5-HT2B (pki = 8.0-9.4) and 5-HT2C (pki = 8.6-9.1) receptor. At the 5-HT1A and some other 5-HT receptors it serves as a partial agonist. It is known to have partial agonist effects on other 5-HT receptors as well. In neuronal and platelet culture, Methysergide blocks serotonin action with an IC50 = 18 µM. Originally developed in the 1960′s as a migraine/cluster headache treatment, but discontinued due to significant physiological and pyschotropic side effects. Methysergide is still actively used in research as a 5-HT2 receptor antagonist in both in vivo and in vitro experiments.

Other Notes

Due to the nature of the Hazardous Materials in this shipment, additional shipping charges may be applied to your order. Certain sizes may be exempt from the additional hazardous materials shipping charges. Please contact your local sales office for more information regarding these charges.
Matsuta, Y. et al. 2013. Exp. Neurol.247, 250.
IUHPAR Database 2013.

Shad, K.F., Saeed, S.A. 2007. Exp. Brain Res.183, 411.

Knight, A.R. et al. 2004. Naunyn Schmiedebergs Arch. Pharmacol.370, 114.

Saxena, P.R and Lawang, A. 1985. Arch. Int. Pharmacodyn. Ther.277, 235.
Colpaert, F. C. et al. 1979. Eur. J. Pharmacol.58, 505.

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

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

Certificates of Analysis (COA)

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