CAS Number57432-61-8
SynonymsTarget; References; [2]. Koehler PJ, et al. History of methysergide in migraine. Cephalalgia. 2008 Nov;28(11):1126-35.
Molecular FormulaC24H29N3O6
Molecular Weight455.50400
Purity98.00%
Density1.2744 (rough estimate)
Boiling Point638.4ºC at 760mmHg
Melting Point172ºC (dec)
Appearancewhite
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 57432-61-8 |
| Catalog No. | 2A-9044829 |
| Chinese Name | 马来酸甲麦角新碱 |
| Synonyms | Target; References; [2]. Koehler PJ, et al. History of methysergide in migraine. Cephalalgia. 2008 Nov;28(11):1126-35. |
| Molecular Formula | C24H29N3O6 |
| Molecular Weight | 455.50400 |
| Purity | 98.00 |
| Density | 1.2744 (rough estimate) |
| Boiling Point | 638.4ºC at 760mmHg |
| Melting Point | 172ºC (dec) |
| Appearance | white |
| Water Solubility | H2O: 25 mg/mL |
| Storage Condition | -20°C Freezer |
| Packaging | III |
| Application | Methylergometrine maleate (Methylergonovine maleate) is an ergot alkaloid and the active metabolite of Methysergide, which has vasoconstrictive and uterotonic effects. Methylergometrine maleate is a p |
| PubChem ID | 7847746 |
| SMILES | CCC(CO)NC(=O)C1C=C2c3cccc4[nH]cc(c34)CC2N(C)C1.O=C(O)C=CC(=O)O |
| InChI | 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-/t13-,14+,18-;/m1./s1 |
| InChI Key | NOFOWWRHEPHDCY-DAUURJMHSA-N |
| Hazard Symbols | 6.1(b) |
| Bioactivity | Methylergometrine maleate (Methylergonovine maleate) is an ergot alkaloid and an active metabolite of Methysergide with vasoconstrictive and uterotonic activity. Methylergometrine maleate is a potent, selective and orally active 5-HT receptors antagonist with a pA2 value of 9.6. Methylergometrine maleate has antimigraine and dopaminergic activity. Methylergometrine maleate can used for the prevention and control of postpartum hemorrhage[1][2][3]. Related Catalog Research Areas >> Neurological Disease Signaling Pathways >> GPCR/G Protein >> 5-HT Receptor Signaling Pathways >> Neuronal Signaling >> 5-HT Receptor Target serotonin:9.6 nM (pA2) In Vitro Both Methysergide and Methylergometrine displace the concentration-response curve of 5-HT to the right and depressed the maximum effect ; thus, both agents behaved as non-competitive antagonists of 5-HT. Methylergometrine is approximately 40-times more potent than Methysergide as an antagonist of the 5-HT-induced responses, since the calculated apparent pA2 values are 9.6 and 8.0, respectively[3]. In Vivo Methylergometrine is more potent than Methysergide as a vasoconstrictor on bovine middle cerebral artery and human coronary arteries, an effect on 5-HT1B receptors. Subacute oral administration would result in metabolism of Methysergide to Methylergometrine[2]. References [1]. Meneghetti F, et al. Crystallographic and NMR Investigation of Ergometrine and Methylergometrine, Two Alkaloids from Claviceps purpurea. Molecules. 2020 Jan 14;25(2). pii: E331. [2]. Koehler PJ, et al. History of methysergide in migraine. Cephalalgia. 2008 Nov;28(11):1126-35. [3]. Tfelt-Hansen P, et al. Methylergometrine antagonizes 5 HT in the temporal artery. Eur J Clin Pharmacol. 1987;33(1):77-9. Chemical & Physical Properties Density 1.2744 (rough estimate) Boiling Point 638.4ºC at 760mmHg Melting Point 172ºC (dec) Molecular Formula C24H29N3O6 Molecular Weight 455.50400 Exact Mass 455.20600 PSA 142.96000 LogP 1.96530 Appearance of Characters white Index of Refraction 1.6500 (estimate) InChIKey NOFOWWRHEPHDCY-DAUURJMHSA-N SMILES CCC(CO)NC(=O)C1C=C2c3cccc4[nH]cc(c34)CC2N(C)C1.O=C(O)C=CC(=O)O Storage condition -20°C Freezer Water Solubility H2O: 25 mg/mL |
| Use of | Methylergometrine maleate (Methylergonovine maleate) is an ergot alkaloid and an active metabolite of Methysergide with vasoconstrictive and uterotonic activity. Methylergometrine maleate is a potent, selective and orally active 5-HT receptors antagonist with a pA2 value of 9.6. Methylergometrine maleate has antimigraine and dopaminergic activity. Methylergometrine maleate can used for the prevention and control of postpartum hemorrhage[1][2][3]. Properties Name Methyl Ergonovine Maleate Salt Synonym More Synonyms Methylergometrine maleate Biological Activity Description Methylergometrine maleate (Methylergonovine maleate) is an ergot alkaloid and an active metabolite of Methysergide with vasoconstrictive and uterotonic activity. Methylergometrine maleate is a potent, selective and orally active 5-HT receptors antagonist with a pA2 value of 9.6. Methylergometrine maleate has antimigraine and dopaminergic activity. Methylergometrine maleate can used for the prevention and control of postpartum hemorrhage[1][2][3]. Related Catalog Research Areas >> Neurological Disease Signaling Pathways >> GPCR/G Protein >> 5-HT Receptor Signaling Pathways >> Neuronal Signaling >> 5-HT Receptor serotonin:9.6 nM (pA2) In Vitro Both Methysergide and Methylergometrine displace the concentration-response curve of 5-HT to the right and depressed the maximum effect ; thus, both agents behaved as non-competitive antagonists of 5-HT. Methylergometrine is approximately 40-times more potent than Methysergide as an antagonist of the 5-HT-induced responses, since the calculated apparent pA2 values are 9.6 and 8.0, respectively[3]. In Vivo Methylergometrine is more potent than Methysergide as a vasoconstrictor on bovine middle cerebral artery and human coronary arteries, an effect on 5-HT1B receptors. Subacute oral administration would result in metabolism of Methysergide to Methylergometrine[2]. References [1]. Meneghetti F, et al. Crystallographic and NMR Investigation of Ergometrine and Methylergometrine, Two Alkaloids from Claviceps purpurea. Molecules. 2020 Jan 14;25(2). pii: E331. [2]. Koehler PJ, et al. History of methysergide in migraine. Cephalalgia. 2008 Nov;28(11):1126-35. [3]. Tfelt-Hansen P, et al. Methylergometrine antagonizes 5 HT in the temporal artery. Eur J Clin Pharmacol. 1987;33(1):77-9. Chemical & Physical Properties Molecular Formula C24H29N3O6 Exact Mass 455.20600 PSA 142.96000 LogP 1.96530 Appearance of Characters white Index of Refraction 1.6500 (estimate) InChIKey NOFOWWRHEPHDCY-DAUURJMHSA-N |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 United Nations number European Land Transport Danger Regulations: 1544 International Maritime Transport Danger Regulations: 1544 International Air Transport Danger Regulations: 1544 14.2 United Nations shipping name European Land Transport Dangerous Regulations: ALKALOID SALTS, SOLID, N.O.S. (Methylergometrine maleate) IMDG Code: ALKALOID SALTS, SOLID, N.O.S. (Methylergometrine maleate) International air transport hazard regulations: Alkaloid salts, solid, n.o.s. (Methylergometrine maleate) 14.3 Transport hazard categories European Land Transport Danger Regulations: 6.1 International Maritime Transport Danger Regulations: 6.1 International Air Transport Danger Regulations: 6.1 14.4 Package group European Land Transport Danger Regulations: III International Maritime Transport Danger Regulations: III International Air Transport Danger Regulations: III 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special precautions No data available |
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