METHYSERGIDE MALEATE Struktur

Methysergidhydrogenmaleat

Bezeichnung:Methysergidhydrogenmaleat

CAS-Nr129-49-7

Englisch Name:METHYSERGIDE MALEATE

CBNumberCB8753434

SummenformelC25H31N3O6

Molgewicht469.54

MOL-Datei129-49-7.mol

Synonyma

Methysergidhydrogenmaleat

Methysergidhydrogenmaleat physikalisch-chemischer Eigenschaften

storage temp.	Store at RT
Löslichkeit	DMSO: >10 mg/mL
Aggregatzustand	solid
Farbe	white to off-white
Wasserlöslichkeit	Soluble to 10 mM in water with gentle warming
Stabilität	Hygroscopic

Sicherheit

Kennzeichnung gefährlicher	T
R-Sätze:	25
S-Sätze:	45
RIDADR	UN 2811 6.1/PG 3
WGK Germany	3
RTECS-Nr.	KE5410000
HazardClass	6.1(b)
PackingGroup	III
HS Code	2939690000
Toxizität	mouse,LD50,intravenous,185mg/kg (185mg/kg),"Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 101, 1972.

Gefahreninformationscode (GHS)

METHYSERGIDE MALEATE Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R25:Giftig beim Verschlucken.
S-Sätze Betriebsanweisung:
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
Beschreibung
Methysergide is an agonist of the serotonin (5-HT) receptor subtype 5-HT₁ and an antagonist of 5-HT₂ receptors. It binds to recombinant human 5-HT_1A (K_D = 23.44 nM), 5-HT_1E (K_i = 229.09 nM), 5-HT_1F (K_i = 33.88 nM), and rodent 5-HT_1B receptors (K_D = 1,513.56 nM). It also binds to recombinant human 5-HT_2A (K_i = 2.69 nM) and 5-HT_2C receptors (K_D = 1.26 nM) and is an insurmountable antagonist at 5-HT_2B receptors. It inhibits vasoconstriction induced by 5-HT in isolated postmortem human basilar arterial spiral strips (pA₂ = 8.07). Methysergide decreases external carotid blood flow in a dose-dependent manner in vagosympathectomized dogs, an effect that is inhibited by the 5-HT_1B/1D receptor antagonist GR127935 . It has antinociceptive activity in mouse models of pain induced by intrathecal injection of substance P , glutamate, NMDA , AMPA , or kainic acid. Methysergide reduces zymosan-induced paw edema in rats when administered at a dose of 10 mg/kg. Formulations containing methysergide were previously used in the prevention and treatment of vascular headaches.
Originator
Sansert ,Sandoz,US,1962
Verwenden
sedative
Verwenden
Methysergide maleate salt has been used as a serotonin (5HT) receptor antagonist to evaluate the potential systemic effects of methysergide (METH) and 5-HT infusions on production and milk composition in multiparous Holstein cows. It may also be used as a serotonin receptor blocker to identify the serotonergic receptor type involved in the direct excitation of mitral cells in the main olfactory bulb.
Definition
ChEBI: Methysergide maleate is an ergoline alkaloid.
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.
Trademarks
Sansert (Novartis).
Therapeutic Function
Migraine therapy
Biologische Aktivität
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.
Sicherheitsprofil
Poison by ingestion and intravenous routes. Experimental reproductive effects. Human mutation effects reported. When heated to decomposition it emits toxic fumes of NOx.
Lager
Store at RT

METHYSERGIDE MALEATE Upstream-Materialien And Downstream Produkte

Methysergidhydrogenmaleat Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

129-49-7, METHYSERGIDE MALEATE Verwandte Suche:

Send Inquriy