Methyl Ergonovine Maleate Salt

  • CAT Number: R008472
  • CAS Number: 57432-61-8
  • Molecular Formula: C24H29N3O6
  • Molecular Weight: 455.511
  • Purity: ≥95%
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Methylergonovine Maleate (CAS 57432-61-8) is the maleate salt of methylergonovine, a semi-synthetic ergot alkaloid with vasoconstrictive and uterotonic effects. Methylergonovine stimulates serotoninergic and dopaminergic receptors as well as inhibits the release of endothelial-derived relaxation factor. This results in arterial vasoconstriction and increased uterine smooth muscle contractions.

Catalog Number R008472
CAS Number 57432-61-8
Molecular Formula

C24H29N3O6

Purity 95%
Target 5-HT Receptor
Solubility Soluble to 25 mM in sterile water
Storage Desiccate at RT
IUPAC Name (6aR,9R)-N-[(2S)-1-hydroxybutan-2-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide;(Z)-but-2-enedioic acid
InChI 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
InChIKey NOFOWWRHEPHDCY-DAUURJMHSA-N
SMILES CCC(CO)NC(=O)C1CN(C2CC3=CNC4=CC=CC(=C34)C2=C1)C.C(=CC(=O)O)C(=O)O
Reference

<br />
1: Bateman BT, Huybrechts KF, Hernandez-Diaz S, Liu J, Ecker JL, Avorn J.<br />
Methylergonovine maleate and the risk of myocardial ischemia and infarction. Am J<br />
Obstet Gynecol. 2013 Nov;209(5):459.e1-459.e13. doi: 10.1016/j.ajog.2013.07.001.<br />
Epub 2013 Jul 11. PubMed PMID: 23850529; PubMed Central PMCID: PMC4103983.<br />
2: Saper JR, Evans RW. Oral methylergonovine maleate for refractory migraine and<br />
cluster headache prevention. Headache. 2013 Feb;53(2):378-81. doi:<br />
10.1111/head.12033. Review. PubMed PMID: 23432443.<br />
3: Hakim S, Khan RM, Maroof M, Usmani H, Huda W, Jafri F. Methylergonovine<br />
maleate (methergine) relieves postdural puncture headache in obstetric patients.<br />
Acta Obstet Gynecol Scand. 2005 Jan;84(1):100. PubMed PMID: 15603581.<br />
4: Borri P, Gerli P, Antignani FL, Bindi L, Cozzi C, Moscarella G, Buzzoni P.<br />
Methylergonovine maleate: a proposal for its more specific use. Biol Res<br />
Pregnancy Perinatol. 1986;7(3):128-30. PubMed PMID: 3490881.<br />
5: Gonz&aacute;lez P, Gay&aacute;n P, Pineda G, Herrera R, Leyton M. [Plasma prolactin in the<br />
puerperium and its relation to the use of methylergonovine maleate]. Rev Chil<br />
Obstet Ginecol. 1984;49(3):149-55. Spanish. PubMed PMID: 6543471.<br />
6: Narvekar MR, Pachauri S, Mhatre V, Ganguli AC. The role of methylergonovine<br />
maleate in augmenting extraamniotic saline for midtrimester abortion. Int J<br />
Gynaecol Obstet. 1978;15(6):545-7. PubMed PMID: 29806.<br />
7: Kuczkowski KM. Myocardial ischemia induced by intramyometrial injection of<br />
methylergonovine maleate. Anesthesiology. 2004 Apr;100(4):1043. PubMed PMID:<br />
15087660.<br />
8: Herrinton LJ, Friedman GD. Methylergonovine maleate and risk of breast cancer.<br />
Ann Epidemiol. 1997 Aug;7(6):427-9. PubMed PMID: 9279452.<br />
9: Mueller L, Gallagher RM, Ciervo CA. Methylergonovine maleate as a cluster<br />
headache prophylactic: a study and review. Headache. 1997 Jul-Aug;37(7):437-42.<br />
Review. PubMed PMID: 9277027.<br />
10: Kirchhoefer RD. Fluoremetric determination of methylergonovine maleate and<br />
ergonovine maleate in tablets and injections. J Assoc Off Anal Chem. 1978<br />
Nov;61(6):1433-4. PubMed PMID: 730649.<br />
11: Kirchhoefer RD, Wells CE. Semiautomated analysis of ergonovine maleate or<br />
methylergonovine maleate tablets and injections by colorimetric or fluorometric<br />
systems. J Assoc Off Anal Chem. 1975 Sep;58(5):879-83. PubMed PMID: 239918.<br />
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