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ERGOTAMINE

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ERGOTAMINE

EINECS 204-023-9
CAS No. 113-15-5 Density 1.47 g/cm3
Solubility Melting Point
Formula C33H35N5O5 Boiling Point 914.5 °C at 760 mmHg
Molecular Weight 581.63 Flash Point 506.9 °C
Transport Information UN 1544 Appearance
Safety Risk Codes
Molecular Structure Molecular Structure of 113-15-5 (Ergotaman-3',6',18-trione,12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5'a)-) Hazard Symbols
Synonyms

Ergotamine(8CI);Ergotamin;NSC 95090;

 

Chemistry

MF: C33H35N5O5
MW: 581.6615
EINECS: 204-023-9
Product Categories: Organics
Mol File: 113-15-5.mol
Ergotamine is an ergopeptine and part of the ergot family of alkaloids; it is structurally and biochemically closely related to ergoline. It possesses structural similarity to several neurotransmitters, and has biological activity as a vasoconstrictor.
Synonyms:12’-hydroxy-2’-methyl-5’alpha-(phenylmethyl)ergotaman-3’,6’,18-trione;18-trione,12’-hydroxy-2’-methyl-5’-(phenylmethyl)-6(5’alpha)-ergotaman-3;6’,18-trione,12’-hydroxy-2’-methyl-5’-(phenylmethyl)-ergotaman-3(5’-alph;ergotamin;ergotamine;Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(phenylmethyl)-, (5'α)-;Ergotamine (8CI);NSC 95090
The structure of Ergotamine(113-15-5) is:

              


 

Uses

1、Ergotamine(113-15-5) is used medicinally for treatment of acute migraine attacks (sometimes in combination with caffeine), and to induce childbirth and prevent post-partum haemorrhage.
2、In high doses ergotamine is conducive to vascular stasis, thrombosis and gangrene. It can increase uterine contractivity and occasionally is used therapeutically immediately post-partum to decrease uterine bleeding.

Toxicity Data With Reference

1.   

cyt-hmn:lym 100 µg/L/24H

   MUREAV    Mutation Research. 48 (1977),205.
2.   

ivn-rbt LD50:100 mg/kg

   EXPEAM    Experientia. 33 (1977),1552.
3.   

scu-frg LDLo:33 mg/kg

   AIPTAK    Archives Internationales de Pharmacodynamie et de Therapie. 27 (1923),459.

Consensus Reports

Ergotamine(113-15-5) is reported in EPA TSCA Inventory.

Safety Profile

Poison by intravenous and subcutaneous routes. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

Specification

Mechanism of action
The mechanism of action of ergotamine is complex.The molecule shares structural similarity with neurotransmitters such as serotonin, dopamine, and adrenaline and can thus bind to several receptors acting as an agonist. Ergotamine also has effects on the dopamine and noradrenaline receptors. It is its action on the D2 dopamine and 5-HT1A receptors that can cause some side effects.

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