Emetine

Emetine

Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	P01AX02 (WHO) QP51AX02 (WHO)
Identifiers
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
CAS Number	483-18-1 Y
PubChem (CID)	10219
ChemSpider	9802 Y
UNII	X8D5EPO80M Y
KEGG	C09421 N
ChEBI	CHEBI:4781 Y
ChEMBL	CHEMBL50588 Y
ECHA InfoCard	100.006.903
Chemical and physical data
Formula	C29H40N2O4
Molar mass	480.639 g/mol
3D model (Jmol)	Interactive image
SMILES O(c1cc2c(cc1OC)[C@H](NCC2)C[C@H]5C[C@H]4c3c(cc(OC)c(OC)c3)CCN4C[C@@H]5CC)C
InChI InChI=1S/C29H40N2O4/c1-6-18-17-31-10-8-20-14-27(33-3)29(35-5)16-23(20)25(31)12-21(18)11-24-22-15-28(34-4)26(32-2)13-19(22)7-9-30-24/h13-16,18,21,24-25,30H,6-12,17H2,1-5H3/t18-,21-,24+,25-/m0/s1 Y Key:AUVVAXYIELKVAI-CKBKHPSWSA-N Y
NY (what is this?)

Emetine is a drug used as both an anti-protozoal and to induce vomiting. It is produced from the ipecac root. It takes its name from its emetic properties.

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, 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.

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 so that adverse events can be addressed.

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 group), but it produces fewer side effects.

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