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Substance Name: Emetine [BAN]
RN: 483-18-1
UNII: X8D5EPO80M
InChIKey: AUVVAXYIELKVAI-CKBKHPSWSA-N

Note

  • 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.

Molecular Formula

  • C29-H40-N2-O4

Molecular Weight

  • 480.645
 

Classification Codes

  • Amebicides
  • Anthelmintics
  • Anti-Infective Agents
  • Antinematodal Agents
  • Antiparasitic Agents
  • Antiprotozoal Agents
  • Autonomic Agents
  • Cathartics
  • Central Nervous System Agents
  • Drug / Therapeutic Agent
  • Emetics
  • Enzyme Inhibitors
  • Gastrointestinal Agents
  • Human Data
  • Mutation Data
  • Natural Product
  • Peripheral Nervous System Agents
  • Protein Synthesis Inhibitors
  • Skin / Eye Irritant
  • Tumor Data
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Names and Synonyms

Name of Substance

  • Emetine
  • Emetine [BAN]

MeSH Heading

  • Emetine

Synonyms

  • 6',7',10,11-Tetramethoxyemetan
  • BRN 0100829
  • Cephaeline methyl ether
  • Cephaline-O-methyl ether
  • EINECS 207-592-1
  • Emetan, 6',7',10,11-tetramethoxy-
  • Emetin
  • Emetine
  • HSDB 2150
  • Methyl cephaeline
  • NSC-33669
  • UNII-X8D5EPO80M

Systematic Names

  • 2H-Benzo(a)quinolizine, 3-ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2-((1,2,3,4-tetrahydro-6,7-dimethoxy-1-isoquinolyl)methyl)-
  • Emetan, 6',7',10,11-tetramethoxy-
  • Emetine

Registry Numbers

CAS Registry Number

  • 483-18-1

FDA UNII

  • X8D5EPO80M

Related Registry Number

  • 316-42-7 (di-hydrochloride)

System Generated Number

  • 0000483181

Structure Descriptors

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

InChIKey

AUVVAXYIELKVAI-CKBKHPSWSA-N

Smiles

CC[C@H]1CN2CCc3cc(c(cc3[C@@H]2C[C@@H]1C[C@@H]4c5cc(c(cc5CCN4)OC)OC)OC)OC

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intravenous 10mg/kg (10mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
cat LDLo subcutaneous 8mg/kg (8mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
guinea pig LDLo intravenous 7mg/kg (7mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
guinea pig LDLo subcutaneous 70mg/kg (70mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
man LDLo unreported 2941ug/kg (2.941mg/kg)   "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
man TDLo subcutaneous 10mg/kg/10D (10mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)

GASTROINTESTINAL: OTHER CHANGES
Cancer Chemotherapy Reports, Part 1. Vol. 57, Pg. 423, 1973.
mouse LD50 intraperitoneal 12mg/kg (12mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 104, Pg. 421, 1952.
rabbit LDLo intravenous 2mg/kg (2mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
rabbit LDLo subcutaneous 30mg/kg (30mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
rat LD50 intraperitoneal 12mg/kg (12mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 104, Pg. 421, 1952.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 74 deg C   EXP
log P (octanol-water) 5.200 (none)   EST
Water Solubility 984 mg/L 15 EXP
Vapor Pressure 2.47E-12 mm Hg 25 EST
Henry's Law Constant 4.99E-16 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.74E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.