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

solubility 

DMSO:55.36(Max Conc. mg/mL);100.0(Max Conc. mM)

form 

White solid with a faint yellow cast

Water Solubility 

Soluble to 100 mM in water

Merck 

14,3559

Stability:

Stable. Combustible. Incompatible with strong oxidizing agents. Light and heat sensitive.

EPA Substance Registry System

Emetine, 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

F 

3-8-10

HazardClass 

6.1(a)

PackingGroup 

I

Toxicity

LD50 (calculated as base) in mice (mg/kg): 32 s.c.; 30 orally (Child)

Emetine dihydrochloride Usage And Synthesis

Description

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.
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.

References

https://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 Properties

white powder or crystals

Chemical Properties

Emetine dihydrochloride is a colorless, combustible powder which turns yellow on exposure to heat or light.

Uses

Anti-amebic.

Uses

Emetine, 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.

Uses

Emetine dihydrochloride has been used:

• as a protein synthesis inhibitor to study its effects on human papillomavirus type 8 E2 protein half-life
• to study its effects on the stress granules assembly
• as a chain-elongation inhibitor in puromycin assay for protein synthesis

Definition

ChEBI: Emetine dihydrochloride is the dihydrochloride salt of emetine. It has a role as an antiprotozoal drug, an antiviral agent, an antineoplastic agent, an antimalarial, an autophagy inhibitor, an emetic, a protein synthesis inhibitor and an anticoronaviral agent. It contains an emetine(2+).

General Description

Clusters 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 Reactions

Water soluble.

Reactivity Profile

When 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 Hazard

EMETINE 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 Hazard

When 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

Biochem/physiol Actions

Emetine dihydrochloride is a member of the ipecac alkaloids family. It can mediate inhibition of protein and nucleic acid synthesis. It exhibits antiviral activity against dengue virus infection and severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2). Emetine dihydrochloride exhibits anti-proliferative effects against bladder cancer cells. It also possesses anti-protozoal activity.

Mechanism of action

Epinephrine, 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 Profile

A 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 Exposure

Emetine 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

First aid

If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit.Emetine is an alkaloid. Procedures for alkaloid salts are asfollows. Move victim to fresh air; call emergency medicalcare. If not breathing, give artificial respiration. If breathingis difficult, give oxygen. In case of contact with material,immediately flush skin or eyes with running water for atleast 15 min. Speed in removing material from skin is ofextreme importance. Remove and isolate contaminatedclothing and shoes at the site. Keep victim quiet and maintain normal body temperature. Effects may be delayed;keep victim under observation.

storage

Store at -20°C

Shipping

UN1544 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 Methods

It 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.]

Incompatibilities

Incompatible 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

Emetine dihydrochloride(316-42-7)Related Product Information

• 2-[2-(Methylamino)benzoyl]-3,4-dihydro-β-carboline-1(2H)-one
• Xanthiside
• MINIMALE LIEFERMENGE
• L-Hyoscyamine
• Etimicin Sulphate
• FORSYTHIN
• Donepezil Hydrochloride
• ORIENTIN
• Rhamnosylvitexin
• HACHIMYCIN
• Tetramethoxymethane
• Emetine
• Emetine dihydrochloride
• EMETINE DIHYDROCHLORIDE HYDRATE,(+)-EMETINE DIHYDROCHLORIDE HYDRATE
• EMETINE DIHYDROCHLORIDE MM(CRM STANDARD)
• EMETINE DIHYDROCHLORIDE(REAGENT / STANDARD GRADE)
• Emetine dihydrochloride tetrahydrate
• (+)-EMETINE DIHYDROCHLORIDE HYDRATE 97