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Emetine (Molecule of the Month for September 2011)



Emetine is a drug used as both an anti-protozoal - used in treatment of protozoan infection - and to induce vomiting. It is produced from the ipecac root. Early use of emetine was in the form of oral administration of the extract of ipecac root, or ipecacuanha. This extract was originally thought to contain only one alkaloid, emetine, but was found to contain several, including cephaeline, emetine, psychotrine and others. Although this therapy was reportedly successful, the extract caused vomiting in many patients which reduced its utility.

The identification of emetine as a more potent agent improved the treatment of amoebiasis. While use of emetine still caused nausea, it was more effective than the crude extract of ipecac root. Additionally, emetine could be administered hypodermically which still produced nausea, but not to the degree experienced in oral administration. Although it is a potent antiprotozoal, the drug also can interfere with muscle contractions, leading to cardiac failure in some cases. Because of this, in some uses it is required to be administered in a hospital environment so that adverse events can be addressed.

Emetine dihydrochloro hydrate is used in the laboratory to block protein synthesis in eukaryotic cells. It does this by binding to the 40S subunit of the ribosome. This can thus be used in the study of protein degradation in cells.

Formal Chemical Name (IUPAC)
(2S,3R,11bS)-2-{[(1R)-6,7-Dimethoxy-1,2,3,4- tetrahydroisoquinolin-1-yl]methyl}-3-ethyl-9,10- dimethoxy-2,3,4,6,7,11b-hexahydro-1H-pyrido [2,1-a]isoquinoline

References

http://en.wikipedia.org/wiki/Emetine

http://en.wikipedia.org/wiki/Carapichea_ipecacuanha

Picture of Emetine

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Emetine structure
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Picture of Emetine

C29H40N2O4



Update by Karl Harrison
(Molecule of the Month for September 2011 )