CAS 57432-61-8|Methylergometrine maleate
Introduction：Basic information about CAS 57432-61-8|Methylergometrine maleate, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Methylergometrine maleate | ||
|---|---|---|---|
| CAS Number | 57432-61-8 | Molecular Weight | 455.50400 |
| Density | 1.2744 (rough estimate) | Boiling Point | 638.4ºC at 760mmHg |
| Molecular Formula | C24H29N3O6 | Melting Point | 172ºC (dec) |
| MSDS | / | Flash Point | / |
| Symbol | GHS06, GHS08 | Signal Word | Danger |
Names
| Name | Methyl Ergonovine Maleate Salt |
|---|---|
| Synonym | More Synonyms |
Methylergometrine maleate BiologicalActivity
| 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 DiseaseSignaling Pathways >>GPCR/G Protein >>5-HT ReceptorSignaling 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 |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATA - TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 93 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 23 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 187 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 6 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 85 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - rabbit
- DOSE/DURATION :
- 2600 ug/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intramuscular
- DOSE :
- 4 ug/kg
- SEX/DURATION :
- female 36 week(s) after conception
- TOXIC EFFECTS :
- Reproductive - Maternal Effects - uterus, cervix, vagina Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system
MUTATION DATA - TYPE OF TEST :
- Sister chromatid exchange
- TEST SYSTEM :
- Rodent - hamster Ovary
- DOSE/DURATION :
- 10 nmol/L
- REFERENCE :
- TCMUD8 Teratogenesis, Carcinogenesis, and Mutagenesis. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1980- Volume(issue)/page/year: 8,169,1988 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X5464 No. of Facilities: 98 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 1396 (estimated) No. of Female Employees: 807 (estimated)
- TYPE OF TEST :
- Sister chromatid exchange
- TEST SYSTEM :
- Rodent - hamster Ovary
- DOSE/DURATION :
- 10 nmol/L
- REFERENCE :
- TCMUD8 Teratogenesis, Carcinogenesis, and Mutagenesis. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1980- Volume(issue)/page/year: 8,169,1988 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X5464 No. of Facilities: 98 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 1396 (estimated) No. of Female Employees: 807 (estimated)
Safety Information
| Symbol | GHS06, GHS08 |
|---|---|
| Signal Word | Danger |
| Hazard Statements | H301 + H311 + H331-H361 |
| Precautionary Statements | Missing Phrase - N15.00950417-P261-P280-P302 + P352 + P312-P304 + P340 + P312-P403 + P233 |
| Hazard Codes | T |
| Risk Phrases | R23/24/25;R62 |
| Safety Phrases | S36/37/39-S45 |
| RIDADR | UN 1544 |
| WGK Germany | 3 |
| RTECS | KE5500000 |
| Packaging Group | III |
| Hazard Class | 6.1(b) |
Articles5
More Articles| Methylergometrine: adverse effects in breastfed infants. Prescrire Int. 23(148) , 102, (2014) | |
| [Reflections of an expert committee of the French Society of Cardiology on the use of methylergometrine maleate (Methergin) for the detection of abnormal coronary vasomotricity]. Arch. Mal. Coeur Vaiss. 88(2) , 247-53, (1995) | |
| Oral methylergonovine maleate for refractory migraine and cluster headache prevention. Headache 53(2) , 378-81, (2013) |
Synonyms
| (6aR,9R)-N-[(2S)-1-hydroxybutan-2-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide,(Z)-but-2-enedioic acid |
