113-42-8 Usage
Chemical Properties
Shiny crystals; melts at 172°C (341.6°F);moderately soluble in water, dissolves readilyin alcohol and acetone.
Originator
Methergine,Sandoz,US,1948
Uses
Different sources of media describe the Uses of 113-42-8 differently. You can refer to the following data:
1. Methylergonovine is a drug currently used as a smooth muscle constrictor during postpartum hemorrhage, as an inhibitor of the inflammasome complex in ASC-mediated procaspase-1 activation screening.
2. This compound is a homologue of ergonovine.It is used in the treatment of postpartumhemorrhage.
3. Oxytocic.
Manufacturing Process
To a freshly prepared solution of 2 parts of d-isolysergic acid azide in 300 parts of either is added an ethereal solution of 2 parts of d-2-aminobutanol-1 and the mixture is left to stand at room temperature during 12 hours. The yellowish clear solution is then washed several times with some water, dried over sodium sulfate and the ether evaporated in vacuo. The crystallized residue is treated with a small quantity of acetone and filtered. Yield: 2.2 parts of d-isolysergic acid-d-1-hydroxybutylamide-2. On recrystallization from
some hot methanol the new compound is obtained in form of beautiful
polygonal crystals that melt with some decomposition at 192° to 194°C
(corr.).1 part of the iso-compound is then dissolved in 10 parts of absolute ethanol
and an alcoholic potassium hydroxide solution is added thereto. The mixture is
left to stand at room temperature during 45 minutes. After this time
equilibrium is reached between lysergic acid and the isolysergic acid forms,
which can be checked by determination of the constancy of the optical
rotation of the solution. When this point is reached, potassium hydroxide is
transformed into potassium carbonate by bubbling through the solution a
stream of carbon dioxide; the thick crystal paste of potassium carbonate is
then diluted with 50 parts of ether, filtered and washed again with 50 parts of
ether.The alcoholic ethereal filtrate is then dried over calcined potassium carbonate
and the solution evaporated, whereby 0.9 to 1 part of a mixture of d-lysergic
acid-d-1-hydroxybutylamide-2 and of d-isolysergic acid-d-1-
hydroxybutylamide-2 is obtained. In order to separate the isomers, the
residue is dissolved in 15 parts of hot chloroform and filtered from the small
quantity of inorganic salt, whereby on cooling down, the difficultly soluble
chloroform compound of d-lysergic acid-d-1-hydroxybutylamide-2 crystallizes
out. Yield: 0.4 part. This compound can be recrystallized from hot benzene,
whereby crystals melting with some decomposition at 172°C (corr.) are
obtained. It may then be reacted with maleic acid to give the maleate.
Brand name
Methergine(Novartis).
Therapeutic Function
Oxytocic
Health Hazard
The toxic effects due to methylergonovine inhumans include nausea, vomiting, dizziness,and hypertension. The oral and intravenousLD50 values in mice are 187 and 85 mg/kg,respectively.
Biological Activity
Active metabolite of methysergide ; uterotonic agent and oxytocic.
Safety Profile
Poison by ingestion and intravenous routes. When heated to decomposition it emits toxic fumes of NOx.
Check Digit Verification of cas no
The CAS Registry Mumber 113-42-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 3 respectively; the second part has 2 digits, 4 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 113-42:
(5*1)+(4*1)+(3*3)+(2*4)+(1*2)=28
28 % 10 = 8
So 113-42-8 is a valid CAS Registry Number.
InChI:InChI=1/C20H25N3O2/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/h4-7,9,13-14,18,21,24H,3,8,10-11H2,1-2H3,(H,22,25)/p+1/t13-,14+,18-/m1/s1
113-42-8Relevant articles and documents
Crystallographic and NMR investigation of ergometrine and methylergometrine, two alkaloids from claviceps purpurea
Ciceri, Samuele,Elahi, Shahrzad Reza,Ferraboschi, Patrizia,Grisenti, Paride,Meneghetti, Fiorella,Mori, Matteo
, (2020)
Ergometrine and methylergometrine are two alkaloids that are used as maleate salts for the prevention and control of postpartum hemorrhage. Although the two molecules have been known for a long time, few and discordant crystallographic and NMR spectroscopic data are available in the literature. With the aim of providing more conclusive data, we performed a careful NMR study for the complete assignment of the 1H, 13C, and 15N NMR signals of ergometrine, methylergometrine, and their maleate salts. This information allowed for a better definition of their conformational equilibria. In addition, the stereochemistry and the intermolecular interactions in the solid state of the two maleate salts were deeply investigated by means of single-crystal X-ray diffraction, showing the capability of these derivatives to act as both hydrogen-bond donors and acceptors, and evidencing a correlation between the number of intermolecular interactions and their different solubility.
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