Emetine

Emetine

File:Emetine.svg
Systematic (IUPAC) name
(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
Identifiers
CAS Number	483-18-1
ATC code	P01AX02 (WHO) QP51AX02
PubChem	CID 10219
ChemSpider	9802
Chemical data
Formula	C29H40N2O4
Molar mass	480.639 g/mol[[]]
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Emetine is a drug used as both an anti-protozoal and to induce vomiting. It is produced from the ipecac root.

Early emetine-based preparations

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. In some cases, it was given with opioids to reduce nausea. Other suggestions to reduce nausea involved coating the drug to allow it to be released after digestion in the stomach.

Use of emetine as anti-amoebic

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 anti-protozoal, 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.

Dehydroemetine

Main article: dehydroemetine

Dehydroemetine is a synthetically produced antiprotozoal agent similar to emetine in its anti-amoebic properties and structure (they differ only in a double bond next to the ethyl radical), but it produces fewer side effects.

Cephaeline

Main article: cephaeline

Cephaeline is a desmethyl analog of emetine also found in ipecac root.

Use in blocking protein synthesis

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 (Jimenez et al., Enzymatic and nonenzymatic translocation of yeast polysomes. Site of action of a number of inhibitors. Biochemistry, 1977 16;4727-4730). This can thus be used in the study of protein degradation in cells.

Side Effects

Heavy/ overusage of emetine can carry the risk of developing proximal myopathy and/or cardiomyopathy.

References

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