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57432-61-8

57432-61-8 structure
57432-61-8 structure
  • Name: Methylergometrine maleate
  • Chemical Name: Methyl Ergonovine Maleate Salt
  • CAS Number: 57432-61-8
  • Molecular Formula: C24H29N3O6
  • Molecular Weight: 455.50400
  • Catalog: API Hormone and endocrine-regulating drugs Pituitary hormone
  • Create Date: 2018-06-30 23:00:21
  • Modify Date: 2024-01-03 19:21:56
  • 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].

Name Methyl Ergonovine Maleate Salt
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
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
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.

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 white
Index of Refraction 1.6500 (estimate)
Storage condition -20°C Freezer
Water Solubility H2O: 25 mg/mL

CHEMICAL IDENTIFICATION

RTECS NUMBER :
KE5500000
CAS REGISTRY NUMBER :
57432-61-8
LAST UPDATED :
199509
DATA ITEMS CITED :
9
MOLECULAR FORMULA :
C20-H25-N3-O2.C4-H4-O4
MOLECULAR WEIGHT :
455.56
WISWESSER LINE NOTATION :
T C6656 1A P GN LM CUTT&&J EVMY2&1Q G1 &OV1U1VO 2

HEALTH HAZARD DATA

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)
Symbol GHS06 GHS08
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)