Methylergometrine maleate

[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

[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 of Characters ]:
white

[ Index of Refraction ]:
1.6500 (estimate)

[ Storage condition ]:
-20°C Freezer

[ Water Solubility ]:
H2O: 25 mg/mL

Click to get detail MSDS

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

[ 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)

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)

Names

Biological Activity

Chemical & Physical Properties

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

Safety Information

Articles

Related Compounds