Ergotamine

From BIOL 2P96 Jan 2013 Group 08

Ergotamine is an alkaloid created by the fungus Claviceps purpurea with the molecular formula C₃₃H₃₅N₅O₅.^[1] Along with other compounds in the ergot alkaloid family, it causes ergotism, also known as ergot poisoning, ignis sacer, and St. Anthony's Fire, characterized by one of two sets of symptoms. Convulsive ergotism results in muscle spasms and seizures similar to lock jaw, as well as mental effects (mania and paranoia), gastrointestinal problems (vomiting, nausea, diarrhea), and others (headaches, numb limbs, and itching). Gangrenous ergotism causes the constriction of the vascular system, resulting in poor circulation and even the necrosis and separation of tissue.^[2]

Contents 1 Description of Ergot Fungus 2 History 3 Mechanism of Biological Action 4 References

[edit] Description of Ergot Fungus

Ergot is characterized by enlarged, dark grains on the reproductive structures of cereals. These are the sclerotia of the ergot fungus adn what causes ergotism when consumed.^[3]

[edit] History

Evidence of ergotism stretches back for millennia, as far back as the year 857 in Annales Xantenses^[4] where an outbreak of gangrenous ergotism was recorded. Even Earlier evidence was found in the intestines of a bog mummy, where traces of ergot infected rye was present. ^[5] Other notable outbreaks and deaths include King Magnus of the Swedes, and an outbreak in 1951 in Point-Saint-Esprit.^[6][7]

In 1938 LSD was synthesized by Alfred Hoffmann through the alkaline hydrolysis of ergotamine.^[8]

[edit] Mechanism of Biological Action

Ergotamine has an affinity for 5-HT (5-hydroxytryptamine, also known as serotonin) receptors in the brain as well as dopamine and noradrenaline receptors.^[9] This is due to the similar distances between the amine groups and aromatic ring structures in all the compounds. This binding results in the aforementioned symptoms or ergotism.

[edit] References

1. Sigma alderitch: Dihydroergotamine ( )-tartrate salt. (n.d.). Retrieved from http://www.sigmaaldrich.com/catalog/product/fluka/D6628?

2. Merhoff, G., & Porter, J. (1974). Ergot intoxication: Historical review and description of unusual clinical manifestations. Annals of Surgery, 180(5), 773-779.

3. Ergot. In Encyclopedia Brittanica Online.

4. Unknown. (1909). Annales xantenses et annales vedastini. Hannoverae et Lipsiae

5. Stokilde-Jorgensen, H., Jacobson, N., Warncke, E., & Heinemeier, J. (2008). The intestines of a more than 2000 years old peat-bog man: microscopy, magnetic resonance imaging and 14c-dating. Journal of Archaeological Science, 35(3), 530-534.

6. Sturluson, S. (1225). S. Laing (Ed.), Heimskringla. London: Norroena Society.

7. Gabbai. , Lisbonne, , & Pourquier, (1951). Ergot poisoning at pont st.esprit. British Medical Journal, 2(4732), 650-651.

8. Hofmann, A. (1980). Lsd-my problem child. McGraw-Hill Book Company.

9. Tfelt-Hensen, P., Saxena, P., Dahlof, C., Pascual, J., Lainez, M., Henry, P., Diener, H., Schoenen, J., Ferrari, M., & Goadsby, P. (1999). Ergotamine in the acute treatment of migraine a review and european consensus. Brain: A Journal of Neurology, 123(1), 9-18.