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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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C C Enweronu-Laryea et al.
East African medical journal, 85(9), 463-465 (2009-06-23)
Methylergometrine is probably the most commonly used drug in obstetric care at all levels of the health care system. Many communities in Africa lack skilled birth attendants and adequate health systems; medication errors are more likely to occur and go
Sudden death caused by atypical variant angina.
Franck Laporte et al.
Archives of cardiovascular diseases, 104(8-9), 480-481 (2011-09-29)
Axel de Labriolle et al.
Cardiovascular toxicology, 9(1), 46-48 (2009-02-17)
Ergot derivatives are frequently administrated during cesarean delivery, induced abortion, or post-partum hemorrhage to promote uterine contractions. Ergot derivatives may also induce coronary spasm and intravenous ergonovine is used in cardiac catheterization laboratories as a diagnostic agent. Serious ischemic cardiac
Pavol Zubor et al.
Archives of gynecology and obstetrics, 282(3), 261-267 (2009-09-18)
Ultrasonographic evaluation of the postpartum uterus to prevent retained placental tissue complications is still a matter of debate, and it is difficult to interpret its necessity on the basis of previous studies. We hypothesized that the application of uterotonics on
Kazutoshi Isobe et al.
Nihon Kokyuki Gakkai zasshi = the journal of the Japanese Respiratory Society, 46(12), 1007-1012 (2009-02-07)
A 35-year-old woman underwent endometrial curettage for suspicion of miscarriage. A few minutes after intravenous injection of methylergometrin (0.2 mg) for inducing uterine contraction, blood gas analysis revealed severe hypoxemia. Chest CT showed diffuse ground-glass opacities in both lung fields
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