Chemicals and Drugs

Emetine

The principal alkaloid of ipecac, from the ground roots of Uragoga (or Cephaelis) ipecacuanha or U. acuminata, of the Rubiaceae. It is used as an amebicide in many different preparations and may cause serious cardiac, hepatic, or renal damage and violent diarrhea and vomiting. Emetine inhibits protein synthesis in EUKARYOTIC CELLS but not PROKARYOTIC CELLS.

National Library of MedicineMedical Subject Headings2026

Structured Summary

Abstract

The principal alkaloid of ipecac, from the ground roots of Uragoga (or Cephaelis) ipecacuanha or U. acuminata, of the Rubiaceae. It is used as an amebicide in many different preparations and may cause serious cardiac, hepatic, or renal damage and violent diarrhea and vomiting. Emetine inhibits protein synthesis in EUKARYOTIC CELLS but not PROKARYOTIC CELLS.

Chemical Identity

Chemical Information

Molecular Formula
C29H40N2O4
Molecular Weight
480.6 g/mol
CAS Registry No.
483-18-1
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-benzo[a]quinolizine
InChIKey
AUVVAXYIELKVAI-CKBKHPSWSA-N
SMILES
CC[C@H]1CN2CCC3=CC(=C(C=C3[C@@H]2C[C@@H]1C[C@@H]4C5=CC(=C(C=C5CCN4)OC)OC)OC)OC
MeSH Unique ID
D004640
Source
PubChem CID 10219

MeSH Record

Classification

Broader headings

Related Concepts

Knowledge Graph

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Drug Class

Pharmacological Action

MeSH Record

See Also

MeSH Record

Synonyms

6 entry terms
  • Ipecine
  • Methylcephaeline
  • Emetine Dihydrochloride
  • Emetine Hydrochloride
  • Dihydrochloride, Emetine
  • Hydrochloride, Emetine

MeSH Record

Aspects Covered

27 allowable subheadings

Indexed with the subheadings administration & dosage, adverse effects, agonists, analogs & derivatives, analysis, antagonists & inhibitors, biosynthesis, blood, cerebrospinal fluid, chemical synthesis, chemistry, classification, economics, genetics, history, immunology, isolation & purification, metabolism, pharmacokinetics, pharmacology, poisoning, radiation effects, standards, supply & distribution, therapeutic use, toxicity, urine.

MeSH Hierarchy

Tree Numbers

  1. D03w.132w.316w
  2. D03w.633.100.531.321w

MeSH Record

NLM Classification

QV 255

AMA Style

References

  1. National Library of Medicine. Emetine. Medical Subject Headings (MeSH). 2026. Unique ID D004640. http://id.nlm.nih.gov/mesh/2026/D004640
  2. Emetine. In: Wikipedia. https://en.wikipedia.org/wiki/Emetine
  3. Emetine. In: Wikidata. https://www.wikidata.org/wiki/Q3050386
  4. Emetine. In: PubChem Compound. CID 10219. https://pubchem.ncbi.nlm.nih.gov/compound/10219