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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

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

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Ahmet Yagmur Bas et al.
European journal of pediatrics, 170(5), 633-637 (2010-10-26)
Methylergonovine (MEV) is a semi-synthetic ergot alkaloid used in the prevention and control of postpartum hemorrhage. This report describes 12 newborns born on the same day in a local country hospital in Turkey and developed sepsis-like symptoms and encephalopathy within
Tomoko Ishibashi et al.
Journal of anesthesia, 25(3), 405-408 (2011-03-25)
Neurological deficits associated with methylergometrine have been reported primarily as a result of reversible cerebral vasoconstriction syndromes (RCVS). RCVS are characterized by reversible multifocal vasoconstrictions of the cerebral arteries heralded by acute severe headache with or without neurological deficits. Here
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
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
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