| Identification | Back Directory | [Name]
METHYSERGIDE MALEATE | [CAS]
129-49-7 | [Synonyms]
sansert
NSC-186061
deseril-retard
Deseril, Sansert
maleate(1:1)(salt)
METHYSERGIDE MALEATE
methysergidebimaleate
methysergidedimaleate
Methysergide Maleate, USP
methysergide maleate salt
METHYLSERGIDE MALEATE SALT
LWYXFDXUMVEZKS-ZVFOLQIPSA-N
methysergidehydrogenmaleate
Methysergide Maleate (350 mg)
Methysergide Maleate (1440003)
METHYSERGIDE MALEATE SEROTONIN ANTAGONIS T
n-((1-hydroxymethyl)propyl)-1-methyl-lysergamidmaleate
1-(hydroxymethyl)propylamideof1-methyl-(+)-lysergicacidhydrogenmaleate
ergoline-8-beta-carboxamide,9,10-didehydro-n-(1-(hydroxymethyl)propyl)-1,6-dim
[8β(S)]-9,10-Didehydro-N-[1-(hydroxymethyl)propyl]-1,6-dimethylergoline-8-carboxamidemaleate
[8B(S)]-9,10-DIDEHYDRO-N-[1-(HYDROXYMETHYL)PROPYL]-1,6-DIMETHYLERGOLINE-8-CARBOXAMIDE MALEATE
[8beta(S)]-9,10-Didehydro-N-[1-(hydroxymethyl)propyl]-1,6-dimethylergoline-8-carboxamide maleate | [EINECS(EC#)]
204-950-9 | [Molecular Formula]
C25H31N3O6 | [MDL Number]
MFCD00083185 | [MOL File]
129-49-7.mol | [Molecular Weight]
469.53 |
| Chemical Properties | Back Directory | [storage temp. ]
Store at RT | [solubility ]
DMSO: >10 mg/mL
| [form ]
solid
| [color ]
white to off-white
| [Water Solubility ]
Soluble to 10 mM in water with gentle warming | [Stability:]
Hygroscopic | [InChIKey]
LWYXFDXUMVEZKS-ZVFOLQIPSA-N | [SMILES]
[n]1(c2c3c(c1)C[C@H]4N(C[C@@H](C=C4c3ccc2)C(=O)N[C@H](CO)CC)C)C.OC(=O)\C=C/C(=O)O |
| Hazard Information | Back Directory | [Uses]
sedative | [Brand name]
Sansert (Novartis). | [Biological Activity]
Mixed 5-HT 1 /5-HT 2 receptor antagonist. | [Description]
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-HT1A (KD = 23.44 nM), 5-HT1E (Ki = 229.09 nM), 5-HT1F (Ki = 33.88 nM), and rodent 5-HT1B receptors (KD = 1,513.56 nM). It also binds to recombinant human 5-HT2A (Ki = 2.69 nM) and 5-HT2C receptors (KD = 1.26 nM) and is an insurmountable antagonist at 5-HT2B 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-HT1B/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 | [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. | [Therapeutic Function]
Migraine therapy | [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. | [storage]
Store at RT | [References]
[1] D HOYER. International Union of Pharmacology classification of receptors for 5-hydroxytryptamine (Serotonin).[J]. Pharmacological Reviews, 1994, 46 2: 157-203.
[2] MARTHA B RAMíREZ ROSAS. Activation of 5-hydroxytryptamine1B/1D/1F receptors as a mechanism of action of antimigraine drugs.[J]. Expert Opinion on Pharmacotherapy, 2013, 14 12: 1599-1610. DOI: 10.1517/14656566.2013.806487
[3] MüLLER-SCHWEINITZER E. Vascular effects of ergot alkaloids: A study on human basilar arteries[J]. General Pharmacology-the Vascular System, 1983, 14 1: Pages 95-102. DOI: 10.1016/0306-3623(83)90073-3
[4] CARLOS M VILLALóN. Canine external carotid vasoconstriction to methysergide, ergotamine and dihydroergotamine: role of 5-HT1B/1D receptors and α2-adrenoceptors[J]. British Journal of Pharmacology, 2009, 126 3: 585-594. DOI: 10.1038/sj.bjp.0702324
[5] KI-MYUNG CHUNG. Antinociceptive effects of methysergide in various pain models.[J]. Pharmacology, 2003, 69 2: 93-101. DOI: 10.1159/000072362
[6] J.P. TARAYRE. Pharmacological studies on zymosan inflammation in rats and mice. 1: Zymosan-induced paw oedema in rats and mice[J]. Pharmacological research, 1989, 21 4: Pages 375-384. DOI: 10.1016/1043-6618(89)90155-2 |
| Safety Data | Back Directory | [Hazard Codes ]
T | [Risk Statements ]
25 | [Safety Statements ]
45 | [RIDADR ]
UN 2811 6.1/PG 3
| [WGK Germany ]
3
| [RTECS ]
KE5410000
| [HazardClass ]
6.1(b) | [PackingGroup ]
III | [HS Code ]
2939690000 | [Storage Class]
6.1C - Combustible, acute toxic Cat.3
toxic compounds or compounds which causing chronic effects | [Hazard Classifications]
Acute Tox. 3 Oral | [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. | [Toxicity]
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. |
|
| Company Name: |
Spectrum Chemical Manufacturing Corp.
|
| Telephone: |
021-021-021-67601398-809-809-809 15221380277 |
| Website: |
www.spectrumchemical.com/oa_html/index.jsp?minisite=10020&respid=22372&language=us |
| Company Name: |
Sigma-Aldrich
|
| Telephone: |
021-61415566 800-8193336 |
| Website: |
https://www.sigmaaldrich.cn |
| Company Name: |
Energy Chemical
|
| Telephone: |
400-0056266 |
| Website: |
www.energy-chemical.com |
|