ergotamine
- CAS NO.:113-15-5
- Empirical Formula: C33H35N5O5
- Molecular Weight: 581.66
- EINECS: 204-023-9
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-08-28 13:53:22
What is ergotamine?
Absorption
The bioavailability of sublingually administered ergotamine has not been determined.
Toxicity
Signs of overexposure include irritation, nausea, vomiting, headache, diarrhea, thirst, coldness of skin, pruritus, weak pulse, numbness, tingling of extremities, and confusion.
The Uses of ergotamine
Ergotamine, 3′,6′,18′-trione,12′-hydroxy-2′-methyl-5′-benzyl-(5α)-ergotamine (12.2.14), is obtained via microbiological synthesis [52].As an α-adrenoblocker, ergotamine exhibits a direct vasoconstricting effect for which it is used in medicine, particularly for alleviation of severe migraine attacks. It is categorically counterproductive in chronic diseases because of the possibility of side effects such as triggering gangrene.
The Uses of ergotamine
Analgesic (specific in migraine).
Indications
For use as therapy to abort or prevent vascular headache, e.g., migraine, migraine variants, or so called "histaminic cephalalgia".
Background
A vasoconstrictor found in ergot of Central Europe. It is an alpha-1 selective adrenergic agonist and is commonly used in the treatment of migraine disorders.
Definition
ChEBI: A peptide ergot alkaloid that is dihydroergotamine in which a double bond replaces the single bond between positions 9 and 10.
brand name
Ergomar (Harvest);Ergostat (Parke-Davis); Wigrettes (Organon).
Pharmacokinetics
Ergotamine is a vasoconstrictor and alpha adrenoreceptor antagonist. The pharmacological properties of ergotamine are extremely complex; some of its actions are unrelated to each other, and even mutually antagonistic. The drug has partial agonist and/or antagonist activity against tryptaminergic, dopaminergic and alpha adrenergic receptors depending upon their site, and it is a highly active uterine stimulant. It causes constriction of peripheral and cranial blood vessels and produces depression of central vasomotor centers. The pain of a migraine attack is believed to be due to greatly increased amplitude of pulsations in the cranial arteries, especially the meningeal branches of the external carotid artery. Ergotamine reduces extracranial blood flow, causes a decline in the amplitude of pulsation in the cranial arteries, and decreases hyperperfusion of the territory of the basilar artery. It does not reduce cerebral hemispheric blood flow.
Metabolism
Hepatic. Ergotamine is metabolized by the liver by largely undefined pathways, and 90% of the metabolites are excreted in the bile.
Purification Methods
Crystallise it from *benzene, then dry it by prolonged heating in high vacuum. It is very hygroscopic. [Beilstein 25 III/IV 964.]
Properties of ergotamine
Melting point: | 241-249℃ |
Boiling point: | 651.33°C (rough estimate) |
alpha | D20 -160° (chloroform) |
Density | 1.0998 (rough estimate) |
refractive index | 1.7500 (estimate) |
pka | pKa 6.40±0.09(H2O
t=24.0) (Uncertain) |
CAS DataBase Reference | 113-15-5 |
Safety information for ergotamine
Computed Descriptors for ergotamine
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