129-49-7 Usage
Description
Methysergide maleate, a chemical compound with the molecular formula C21H27N3O2·C4H4O4, is a semi-synthetic ergot alkaloid derivative. It functions as an agonist for the serotonin (5-HT) receptor subtype 5-HT1 and acts as an antagonist for 5-HT2 receptors. Methysergide maleate is known for its ability to bind to various human and rodent serotonin receptors, exhibiting a range of pharmacological activities.
Uses
Used in Pharmaceutical Industry:
Methysergide maleate is used as a serotonin receptor antagonist for evaluating the potential systemic effects of methysergide and 5-HT infusions on production and milk composition in multiparous Holstein cows. This application aids in understanding the role of serotonin receptors in the physiological processes of dairy cows.
Used in Neuropharmacology Research:
Methysergide maleate is used as a serotonin receptor blocker to identify the specific serotonergic receptor type involved in the direct excitation of mitral cells in the main olfactory bulb. This application contributes to the understanding of serotonin's role in the olfactory system and neuronal signaling.
Used in Pain Management:
Methysergide maleate exhibits antinociceptive activity in mouse models of pain induced by intrathecal injection of substance P, glutamate, NMDA, AMPA, or kainic acid. This application highlights its potential use in the development of pain management therapies.
Used in Inflammation and Edema Treatment:
Methysergide maleate reduces zymosan-induced paw edema in rats when administered at a dose of 10 mg/kg. This property suggests its potential use in the treatment of inflammation and edema in various conditions.
Used in Vascular Headache Treatment:
Formulations containing methysergide maleate were previously used in the prevention and treatment of vascular headaches. This application demonstrates its historical use in managing specific types of headaches.
Brand Name:
Sansert (Novartis) is a brand name under which methysergide maleate was marketed, indicating its commercial availability and use in the medical field.
Originator
Sansert ,Sandoz,US,1962
Manufacturing Process
As described in US Patent 3,218,324, 0.9 part of potassium are dissolved in 500 parts by volume of liquid ammonia, then oxidized with ferric nitrate to potassium amide, after which 4.85 parts of lysergic acid-1'-hydroxybutylamide-2' are dissolved in the obtained mixture. After 15 minutes there are added to the obtained yellow solution 4.1 parts of methyl iodide in 5 parts by volume of ether, the mixture being allowed to stand for 30 more minutes at -60°C. The liquid ammonia is thereupon evaporated and the dry residue is shaken out between water and chloroform. The mixture of bases which remains after the evaporation of the chloroform is chromatographed on a column of 250 parts of aluminum oxide, the desired 1-methyl-lysergic acid-1'- hydroxy-butylamide-2' being washed into the filtrate with chloroform and chloroform-0.2% ethanol. The 1-methyl-lysergic acid-1'hydroxy-butylamide-2' crystallizes from chloroform in the form of plates which melt at 194° to 196°C. Reaction with maleic acid gives the dimaleate, melting at 187° to 188°C.
Therapeutic Function
Migraine therapy
Biological Activity
Mixed 5-HT 1 /5-HT 2 receptor antagonist.
Biochem/physiol Actions
Methysergide maleate, also known as sansert, is a semisynthetic ergot alkaloid ergometrine derivative. Methysergide is a serotonin 1(5-HT1) receptor agonist and a nonselective 5-HT2 and 5-HT7 serotonin receptor antagonist. Methysergide maleate is used as a pharmacological agent to treat migraines and other vascular headaches. But, prolonged and uncontrolled use of this drug may cause Leriche′s syndrome, angina pectoris, acute ischemia of the limbs. In addition, gastrointestinal side effects, such as abdominal cramps, nausea, and diarrhea have also been observed in few patients.
Safety Profile
Poison by ingestion and
intravenous routes. Experimental
reproductive effects. Human mutation effects reported. When heated to
decomposition it emits toxic fumes of NOx.
Check Digit Verification of cas no
The CAS Registry Mumber 129-49-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 9 respectively; the second part has 2 digits, 4 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 129-49:
(5*1)+(4*2)+(3*9)+(2*4)+(1*9)=57
57 % 10 = 7
So 129-49-7 is a valid CAS Registry Number.
InChI:InChI=1/C21H27N3O2.C4H4O4/c1-4-15(12-25)22-21(26)14-8-17-16-6-5-7-18-20(16)13(10-23(18)2)9-19(17)24(3)11-14;5-3(6)1-2-4(7)8/h5-8,10,14-15,19,25H,4,9,11-12H2,1-3H3,(H,22,26);1-2H,(H,5,6)(H,7,8)/b;2-1-/t14-,15+,19-;/m1./s1
