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Merck
CN

M2776

Sigma-Aldrich

Methylergonovine maleate salt

≥98% (TLC)

Synonym(s):

9,10-Didehydro-N-[(S)-1-(hydroxymethyl)propyl]-6-methylergoline-8β-carboxamide maleate salt, Methergine maleate salt

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About This Item

Empirical Formula (Hill Notation):
C20H25N3O2 · C4H4O4
CAS Number:
57432-61-8
Molecular Weight:
455.50
EC Number:
260-734-4
MDL number:
MFCD00078588
UNSPSC Code:
12352200
PubChem Substance ID:
24278543

Key Documents

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Assay

≥98% (TLC)

color

white

solubility

H2O: 25 mg/mL
0.1 M HCl: soluble
ethanol: slightly soluble

SMILES string

[H]\C(=C(/[H])C(O)=O)C(O)=O.[H][C@@]12Cc3c[nH]c4cccc(C1=C[C@H](CN2C)C(=O)N[C@@H](CC)CO)c34

InChI

1S/C20H25N3O2.C4H4O4/c1-3-14(11-24)22-20(25)13-7-16-15-5-4-6-17-19(15)12(9-21-17)8-18(16)23(2)10-13;5-3(6)1-2-4(7)8/h4-7,9,13-14,18,21,24H,3,8,10-11H2,1-2H3,(H,22,25);1-2H,(H,5,6)(H,7,8)/b;2-1-/t13-,14+,18-;/m1./s1

InChI key

NOFOWWRHEPHDCY-DAUURJMHSA-N

Gene Information

human ... DRD1(1812), DRD2(1813), DRD3(1814), DRD4(1815), DRD5(1816)

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Biochem/physiol Actions

Dopamine antagonist interacts with serotonergic, dopaminergic and α-adrenergic systems.
Ergot alkaloid which interacts with serotonergic, dopaminergic and α-adrenergic systems. Dopamine antagonist.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H301 + H311 + H331,H361

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Repr. 2

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
127H47073
087F0262
043K1258

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Alfredo I Niño-Maldonado et al.
Head & face medicine, 5, 21-21 (2009-11-10)
Methylergonovine is an ergot alkaloid widely used in postpartum women. It is also an active metabolite of methysergide and previous studies suggest that it could be effective against refractory headache and cluster headache. The purpose of the present study was
F Aboukhoudir et al.
Annales de cardiologie et d'angeiologie, 61(5), 311-316 (2012-09-11)
To assess the prevalence of coronary artery spasm during dobutamine stress chocardiography (DSE), to describe clinical and echocardiographic characteristics and prognosis. We evaluated all the patients with known or suspected coronary artery disease (CAD) referred to our echocardiography laboratory for
Late onset of coronary vasospasm after administration of methyl-ergometrine for gynecologic bleeding.
Francesco Santoro et al.
International journal of cardiology, 161(2), e29-e30 (2012-04-21)
Taro Nonaka et al.
Obstetrics and gynecology, 117(2 Pt 2), 452-455 (2011-01-22)
Uterine arteriovenous malformations are a rare and potentially life-threatening condition. Medical therapy has not been popular because of the propensity for excessive bleeding in the patient. As a result, the effect of gonadotropin-releasing hormone (Gn-RH) agonists on uterine arteriovenous malformations
D Guindolet et al.
Annales de cardiologie et d'angeiologie, 59(5), 311-313 (2010-09-21)
A 59-year-old man was admitted after cardiac arrest with successful reanimation. There was no significant coronary lesion. We conclude to the diagnosis of coronary spasm after the occurrence of a chest pain with anterior ST elevation reversible with intravenous nitrates.
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