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Emetine dihydrochloride

As the principal alkaloid of ipecac, Emetine dihydrochloride is derived from Uragoga ipecacuanha ground roots, which is used in the treatment of amebiasis. It can also be used as an emetic to induce vomiting.

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Emetine dihydrochloride Basic information
Emetine dihydrochloride Chemical Properties
  • Melting point:240-250 °C (dec., dry matter)(lit.)
  • alpha D +11° (c = 1) to D +21° (c = 8)
  • storage temp. 2-8°C
  • form White solid with a faint yellow cast
  • Merck 14,3559
  • Stability:Stable. Combustible. Incompatible with strong oxidizing agents. Light and heat sensitive.
  • EPA Substance Registry SystemEmetine, dihydrochloride (316-42-7)
Safety Information
  • Hazard Codes T+
  • Risk Statements 28-36/37/38
  • Safety Statements 26-28-36/37-45
  • RIDADR UN 1544 6.1/PG 1
  • WGK Germany 3
  • RTECS JY5250000
  • 3-8-10
  • HazardClass 6.1(a)
  • PackingGroup I
  • ToxicityLD50 (calculated as base) in mice (mg/kg): 32 s.c.; 30 orally (Child)
Emetine dihydrochloride Usage And Synthesis
  • DescriptionAs the principal alkaloid of ipecac, Emetine dihydrochloride is derived from Uragoga ipecacuanha ground roots, which is used in the treatment of amebiasis. It can  also be used as an emetic to induce vomiting.
    Emetine dihydrochloride functions by inhibiting ribosome movement along mRNA, which results in irreversibly blocking protein synthesis in eukaryotic cells  instead of prokaryotic cells. Besides, it has been proved that it can induce hypotension through blocking adrenoreceptors.
  • Referenceshttps://www.scbt.com/scbt/product/emetine-dihydrochloride-316-42-7
    http://www.biovision.com/emetine-dihydrochloride.html
    https://pubchem.ncbi.nlm.nih.gov/compound/3068143#section=Top
  • Chemical Propertieswhite powder or crystals
  • Chemical PropertiesEmetine dihydrochloride is a colorless, combustible powder which turns yellow on exposure to heat or light.
  • UsesAnti-amebic.
  • UsesEmetine, an alkaloid from ipecac, C29H40O4N2, is a white powder with a very bitter taste. The substance is soluble in alcohol and ether, slightly soluble in water. Emetine darkens upon exposure to light. The compound is derived by extraction from the root of Cephalis ipecacuanha (ipecac). It is also made synthetically. Medically, ipecac is useful as an emetic (induces vomiting) for emergency use in the treatment of drug overdosage and in certain cases of poisoning. Ipecac should not be administered to persons in an unconscious state. It should be noted that emesis is not the proper treatment in all cases of potential poisoning. It should not be induced when such substances as petroleum distillates, strong alkali, acids, or strychnine are ingested.
  • General DescriptionClusters of needles after drying at 221°F. Turns yellow on exposure to light or heat. An injectable form of emetine, an anti amebic. Emetine is the active ingredient of ipecac.
  • Air & Water ReactionsWater soluble.
  • Reactivity ProfileWhen heated to decomposition, EMETINE DIHYDROCHLORIDE emits very toxic fumes of chlorides, hydrogen chloride and oxides of nitrogen. Turns yellow on exposure to light or heat [EPA, 1998].
  • Health HazardEMETINE DIHYDROCHLORIDE is highly toxic orally. It is an eye irritant. (Non-Specific -- Emetine) Emetine is classified as extremely toxic. Probable oral lethal dose for humans is 5-50 mg/kg, or between 7 drops and one teaspoon for a 150-lb person.
  • Fire HazardWhen heated to decomposition, EMETINE DIHYDROCHLORIDE emits very toxic fumes of chlorides, hydrogen chloride and oxides of nitrogen. Turns yellow on exposure to light or heat
  • Mechanism of actionEpinephrine, a hormone having a benzenoid structure, C9H13O3N, also called adrenaline. It can be obtained by extraction from the adrenal glands of cattle and also prepared synthetically. Its effect on body metabolism is pronounced, causing an increase in blood pressure and rate of heartbeat. Under normal conditions, its rate of release into the system is constant, but emotional stresses, such as fear or anger rapidly increase the output and result in temporarily heightened metabolic activity. Epinephrine is used for the symptomatic treatment of bronchial asthma and reversible bronchospasm associated with chronic bronchitis and emphysema. The drug acts on both alpha and beta receptor sites. Beta stimulation provides bronchodilator action by relaxing bronchial muscle. Alpha stimulation increases vital capacity by reducing congestion of the bronchial mucosa and by constricting pulmonary vessels.
    Epinephrine has numerous effects on intermediary metabolism. Among these are promotion of hepatic glycogenolysis, inhibition of hepatic gluconeognesis, and inhibition of insulin release. The drug also promotes the release of free fatty acids from triglyceride stores in adipose tissues. Epinephrine produces numerous cardiovascular effects. Epinephrine is particularly useful in treating conditions of immediate hypersensitivity— interactions between antigen and antibody. These mechanisms cause attacks of anaphylaxis, hay fever, hives and allergic asthma. Anaphylaxis can occur after bee and wasp stings, venoms, etc. Although the mechanism is not fully understood, epinephrine can play a lifesaving role in the treatment of acute systemic anaphylaxis.
  • Safety ProfileA poison by ingestion, intraperitoneal, subcutaneous, and intravenous routes. Human systemic effects: diarrhea, distorted perceptions, dyspnea, hallucinations, hypermothty, nausea or vomiting. A human eye irritant. When heated to decomposition it emits very toxic fumes of Cland NOx.
  • Potential ExposureEmetine dihydrochloride is an injectable form of emetine; an alkaloid and antiamebic; the active ingredient of Ipecac. Emetine dihydrochloride is used as chemical reagent, organic intermediate; in pharmaceutical R&D
  • ShippingUN1544 Alkaloids, solid, n.o.s. or Alkaloid salts, solid, n.o.s. poisonous, Hazard Class: 6.1; Labels: 6.1- Poisonous materials, Technical Name Required. UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1- Poisonous materials, Technical Name Required
  • Purification MethodsIt crystallises from MeOH/Et2O, MeOH or Et2O/EtOAc. The free base has m 104-105o, and the (-)-phenylthiourea derivative has m 220-221o (from EtOAc/pet ether, [] D -29.3o (CHCl3)). IR: 3413 (OH) and 2611 (NH+) cm-1; UV at 230nm ( 16 200) and 282nm ( 6 890) max max [Brossi et al. Helv Chim Acta 42 1515 1959, Barash et al. J Chem Soc 3530 1959]. [Beilstein 23 III/IV 3419.]
  • IncompatibilitiesIncompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, and epoxides. Turns yellow on contact with light or heat
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