Synonym
Methylergonovine Maleate; Methylergometrine maleate; Methergine; Methylergobasine maleate; Erezingen; Methylergonovine; Methylergonovine Maleate ;Novartis Brand of Methylergonovine Maleate;
IUPAC/Chemical 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 Key
NOFOWWRHEPHDCY-WLHGVMLRSA-N
InChi Code
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+
SMILES Code
CCC(CO)NC(=O)C1CN(C2CC3=CNC4=CC=CC(=C34)C2=C1)C.C(=CC(=O)O)C(=O)O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Methylergonovine Maleate is the maleate salt of methylergonovine, a semi-synthetic ergot alkaloid with vasoconstrictive and uterotonic effects.
In vitro activity:
In a recently developed in vitro analog of appetitive classical conditioning of feeding in Aplysia, the unconditioned stimulus (US) was electrical stimulation of the esophageal nerve (En). Methylergonovine (1 nM) blocked the pairing-specific increase in fictive feeding that is usually induced by in vitro classical conditioning. The present results and previous observation that methylergonovine also blocks the effects of contingent reinforcement in an in vitro analog of appetitive operant conditioning suggest that DA mediates reinforcement for appetitive associative conditioning of feeding in Aplysia.
Reference: Learn Mem. 2005 May-Jun;12(3):216-20. https://pubmed.ncbi.nlm.nih.gov/15930499/
In vivo activity:
In the rabbit aorta ergometrine (1 mumol/l) and methylergometrine (0.3 mumol/l), but not methysergide, produced small contractions (14% and 7% respectively of the maximal response to 5-HT). Methylergometrine and ergometrine produced surmountable blockade which was accompanied by a non-parallel displacement of the 5-HT concentration-effect curves.
Reference: Naunyn Schmiedebergs Arch Pharmacol. 1990 Aug;342(2):120-9. https://pubmed.ncbi.nlm.nih.gov/2234096/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMSO |
100.0 |
219.53 |
|
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
455.51
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Reyes FD, Mozzachiodi R, Baxter DA, Byrne JH. Reinforcement in an in vitro analog of appetitive classical conditioning of feeding behavior in Aplysia: blockade by a dopamine antagonist. Learn Mem. 2005 May-Jun;12(3):216-20. doi: 10.1101/lm.92905. PMID: 15930499.
2. MacLennan SJ, Martin GR. Actions of non-peptide ergot alkaloids at 5-HT1-like and 5-HT2 receptors mediating vascular smooth muscle contraction. Naunyn Schmiedebergs Arch Pharmacol. 1990 Aug;342(2):120-9. doi: 10.1007/BF00166953. PMID: 2234096.
3. Müller-Schweinitzer E, Tapparelli C. Methylergometrine, an active metabolite of methysergide. Cephalalgia. 1986 Mar;6(1):35-41. doi: 10.1046/j.1468-2982.1986.0601035.x. PMID: 3698092.
In vitro protocol:
1. Reyes FD, Mozzachiodi R, Baxter DA, Byrne JH. Reinforcement in an in vitro analog of appetitive classical conditioning of feeding behavior in Aplysia: blockade by a dopamine antagonist. Learn Mem. 2005 May-Jun;12(3):216-20. doi: 10.1101/lm.92905. PMID: 15930499.
In vivo protocol:
1. MacLennan SJ, Martin GR. Actions of non-peptide ergot alkaloids at 5-HT1-like and 5-HT2 receptors mediating vascular smooth muscle contraction. Naunyn Schmiedebergs Arch Pharmacol. 1990 Aug;342(2):120-9. doi: 10.1007/BF00166953. PMID: 2234096.
2. Müller-Schweinitzer E, Tapparelli C. Methylergometrine, an active metabolite of methysergide. Cephalalgia. 1986 Mar;6(1):35-41. doi: 10.1046/j.1468-2982.1986.0601035.x. PMID: 3698092.
1: Bateman BT, Huybrechts KF, Hernandez-Diaz S, Liu J, Ecker JL, Avorn J.
Methylergonovine maleate and the risk of myocardial ischemia and infarction. Am J
Obstet Gynecol. 2013 Nov;209(5):459.e1-459.e13. doi: 10.1016/j.ajog.2013.07.001.
Epub 2013 Jul 11. PubMed PMID: 23850529; PubMed Central PMCID: PMC4103983.
2: Saper JR, Evans RW. Oral methylergonovine maleate for refractory migraine and
cluster headache prevention. Headache. 2013 Feb;53(2):378-81. doi:
10.1111/head.12033. Review. PubMed PMID: 23432443.
3: Hakim S, Khan RM, Maroof M, Usmani H, Huda W, Jafri F. Methylergonovine
maleate (methergine) relieves postdural puncture headache in obstetric patients.
Acta Obstet Gynecol Scand. 2005 Jan;84(1):100. PubMed PMID: 15603581.
4: Borri P, Gerli P, Antignani FL, Bindi L, Cozzi C, Moscarella G, Buzzoni P.
Methylergonovine maleate: a proposal for its more specific use. Biol Res
Pregnancy Perinatol. 1986;7(3):128-30. PubMed PMID: 3490881.
5: González P, Gayán P, Pineda G, Herrera R, Leyton M. [Plasma prolactin in the
puerperium and its relation to the use of methylergonovine maleate]. Rev Chil
Obstet Ginecol. 1984;49(3):149-55. Spanish. PubMed PMID: 6543471.
6: Narvekar MR, Pachauri S, Mhatre V, Ganguli AC. The role of methylergonovine
maleate in augmenting extraamniotic saline for midtrimester abortion. Int J
Gynaecol Obstet. 1978;15(6):545-7. PubMed PMID: 29806.
7: Kuczkowski KM. Myocardial ischemia induced by intramyometrial injection of
methylergonovine maleate. Anesthesiology. 2004 Apr;100(4):1043. PubMed PMID:
15087660.
8: Herrinton LJ, Friedman GD. Methylergonovine maleate and risk of breast cancer.
Ann Epidemiol. 1997 Aug;7(6):427-9. PubMed PMID: 9279452.
9: Mueller L, Gallagher RM, Ciervo CA. Methylergonovine maleate as a cluster
headache prophylactic: a study and review. Headache. 1997 Jul-Aug;37(7):437-42.
Review. PubMed PMID: 9277027.
10: Kirchhoefer RD. Fluoremetric determination of methylergonovine maleate and
ergonovine maleate in tablets and injections. J Assoc Off Anal Chem. 1978
Nov;61(6):1433-4. PubMed PMID: 730649.
11: Kirchhoefer RD, Wells CE. Semiautomated analysis of ergonovine maleate or
methylergonovine maleate tablets and injections by colorimetric or fluorometric
systems. J Assoc Off Anal Chem. 1975 Sep;58(5):879-83. PubMed PMID: 239918.
