Ergotamine

From BIOL 2P96 Jan 2013 Group 08

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	In 1938 LSD was synthesized by Alfred Hoffmann through the alkaline hydrolysis of ergotamine.[[Image:342px-LSD Structure.svg.png|thumb|Molecular structure of LSD]]<sup>[http://www.psychedelic-library.org/child.htm]</sup>		In 1938 LSD was synthesized by Alfred Hoffmann through the alkaline hydrolysis of ergotamine.[[Image:342px-LSD Structure.svg.png|thumb|Molecular structure of LSD]]<sup>[http://www.psychedelic-library.org/child.htm]</sup>
	==Mechanism of Biological Action==		==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.<sup>[http://brain.oxfordjournals.org/content/123/1/9.full]</sup> [[Image:2-Methyl-5-hydroxytryptamine.png|thumb|Serotonin]][[Image:Dopamine chemical structure.png|thumb|Dopamine]][[Image:Noradrenaline.svg|thumb|Noradrenaline]]	+	Ergotamine has an affinity for 5-HT (5-hydroxytryptamine, also known as serotonin) receptors in the brain as well as dopamine and noradrenaline receptors.<sup>[http://brain.oxfordjournals.org/content/123/1/9.full]</sup> [[Image:2-Methyl-5-hydroxytryptamine.png|thumb|Serotonin]][[Image:Dopamine chemical structure.png|thumb|Dopamine]][[Image:Noradrenaline.svg|thumb|Noradrenaline]]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.

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Revision as of 23:07, 21 March 2013

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]

History

Evidence of ergotism stretches back for millennia, as far back as the year 857 in Annales Xantenses^[3] 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. ^[4] Other notable outbreaks and deaths include King Magnus of the Swedes, and an outbreak in 1951 in Point-Saint-Esprit.^[5][6]

In 1938 LSD was synthesized by Alfred Hoffmann through the alkaline hydrolysis of ergotamine.^[7]

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.^[8] 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.