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Names | |
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IUPAC name (1S,4aR,4bS,7E,8R,8aS,9S,10aR)-Tetradecahydro-9-hydroxy-1,4a,8-trimethyl-7-[2-[2-(methylamino)ethoxy]-2-oxoethylidene]-1-phenanthrenecarboxylic acid methyl ester | |
Other names
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Identifiers | |
PubChem CID | |
Properties | |
C24H39NO5 | |
Molar mass | 421.6 g/mol |
Appearance | White, crystalline powder |
Melting point | 115 |
Miscible | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Erythrophleine is a complex alkaloid and ester of tricyclic diterpene acids derived from many of the plants in the genus erythrophleum. [2] A highly toxic compound, it is most commonly known for its use in West African trials by ordeal. [3] Exposure to erythrophleine can quickly lead to ataxia, dyspnea, heart paralysis, and sudden death. Visible effects of erythrophleine poisoning include induced terror, labored and irregular breathing, convulsions, urination, and vomiting. [4]
Once ingested, erythrophleine primarily acts on the body by disrupting the nervous system. It does this by inhibiting Na-K ATPase, an enzyme that breaks down ATP to generate an electric potential by moving sodium and potassium ions against their concentration gradient. [5] In vertebrates, this potential is used to transmit signals across neural synapses. Normally, sodium-potassium pumps move potassium ions into the nerve cell and sodium ions out, but studies have shown that exposure to erythrophleine reduces this action dramatically. [6] This can have a number of compounding effects including weakened nerve signaling responses and inhibited ability to maintain cellular homeostasis. [7]
While the exact mechanism of this process is unknown, it is likely similar to that of cardiac glycosides. [8] Cardiac glycosides inhibit Na-K ATPase by stabilizing it in the E2-P transition state, preventing sodium ions from being extruded. They do this by mimicking potassium and tightly binding to Na-K ATPase at the potassium active site. [9] The most well-known of these molecules is the active toxin in foxglove. [10]
Erythrophleine's primary use is as a toxin in ancient West African ordeal trials, called sassywood. The process has largely been outlawed, but due to the limited judicial infrastructure of some West African states, ordeal trials still take place with some regularity. [11] Some prominent economists have even argued that sassywood is a more effective substitute to Liberian courts, given the decrepit nature of the country's judicial system. [12]
The main trial consists of creating a poisonous brew derived from the bark of the sasswood tree and administering it to the accused. In order to create the drink, bark of the ordeal tree was simply scraped, powdered, added to water, and allowed to steep. However, many cultures added additional ingredients to the mixture that made the final recipe much more complicated. [4] Once consumed, if the defendant fails to throw up all of the poison before it enters their system, they are pronounced guilty and the poison likely kills them. On the other hand, if they manage to throw up all of the poison and maintain full control of their limbs, then they are cleared of any wrongdoing. [13]
Cardiac glycosides are a class of organic compounds that increase the output force of the heart and decrease its rate of contractions by inhibiting the cellular sodium-potassium ATPase pump. Their beneficial medical uses include treatments for congestive heart failure and cardiac arrhythmias; however, their relative toxicity prevents them from being widely used. Most commonly found as secondary metabolites in several plants such as foxglove plants and milkweed plants, these compounds nevertheless have a diverse range of biochemical effects regarding cardiac cell function and have also been suggested for use in cancer treatment.
Aconitine is an alkaloid toxin produced by various plant species belonging to the genus Aconitum, known also commonly by the names wolfsbane and monkshood. Monkshood is notorious for its toxic properties.
The sodium–potassium pump is an enzyme found in the membrane of all animal cells. It performs several functions in cell physiology.
Neurotoxins are toxins that are destructive to nerve tissue. Neurotoxins are an extensive class of exogenous chemical neurological insults that can adversely affect function in both developing and mature nervous tissue. The term can also be used to classify endogenous compounds, which, when abnormally contacted, can prove neurologically toxic. Though neurotoxins are often neurologically destructive, their ability to specifically target neural components is important in the study of nervous systems. Common examples of neurotoxins include lead, ethanol, glutamate, nitric oxide, botulinum toxin, tetanus toxin, and tetrodotoxin. Some substances such as nitric oxide and glutamate are in fact essential for proper function of the body and only exert neurotoxic effects at excessive concentrations.
Quinidine is a class IA antiarrhythmic agent used to treat heart rhythm disturbances. It is a diastereomer of antimalarial agent quinine, originally derived from the bark of the cinchona tree. The drug causes increased action potential duration, as well as a prolonged QT interval. As of 2019, its IV formulation is no longer being manufactured for use in the United States.
Ouabain or also known as g-strophanthin, is a plant derived toxic substance that was traditionally used as an arrow poison in eastern Africa for both hunting and warfare. Ouabain is a cardiac glycoside and in lower doses, can be used medically to treat hypotension and some arrhythmias. It acts by inhibiting the Na/K-ATPase, also known as the sodium–potassium ion pump. However, adaptations to the alpha-subunit of the Na+/K+-ATPase via amino acid substitutions, have been observed in certain species, namely some herbivore- insect species, that have resulted in toxin resistance.
Batrachotoxin (BTX) is an extremely potent cardiotoxic and neurotoxic steroidal alkaloid found in certain species of beetles, birds, and frogs. The name is from the Greek word βάτραχος, bátrachos, 'frog'. Structurally-related chemical compounds are often referred to collectively as batrachotoxins. In certain frogs, this alkaloid is present mostly on the skin. Such frogs are among those used for poisoning darts. Batrachotoxin binds to and irreversibly opens the sodium channels of nerve cells and prevents them from closing, resulting in paralysis and death. No antidote is known.
Cerbera odollam is a tree species in the family Apocynaceae commonly known as the suicide tree or pong-pong. It bears a fruit known as othalanga whose seeds yield a potent poison called cerberin that has been used for trials by ordeal, suicide, and poisonings.
Cerberin is a type of cardiac glycoside, a steroidal class found in the seeds of the dicotyledonous angiosperm genus Cerbera; including the suicide tree and the sea mango. As a cardiac glycoside, cerberin disrupts the function of the heart by blocking its sodium and potassium ATPase. Cerberin can be used as a treatment for heart failure and arrhythmia.
Cerbera manghas, commonly known as the sea mango, tangena or bintaro is a small evergreen coastal tree growing up to 12 metres (39 ft) tall. It is native to coastal areas in Africa, Asia, Australasia, and the Pacific islands. It is classified as one of the three species in the genus Cerbera that constitute mangroves.
A cardenolide is a type of steroid. Many plants contain derivatives, collectively known as cardenolides, including many in the form of cardenolide glycosides (cardenolides that contain structural groups derived from sugars). Cardenolide glycosides are often toxic; specifically, they are heart-arresting. Cardenolides are toxic to animals through inhibition of the enzyme Na+/K+‐ATPase, which is responsible for maintaining the sodium and potassium ion gradients across the cell membranes.
k-Strophanthidin is a cardenolide found in species of the genus Strophanthus. It is the aglycone of k-strophanthin, an analogue of ouabain. k-strophanthin is found in the ripe seeds of Strophanthus kombé and in the lily Convallaria.
Pumiliotoxin 251D is a toxic organic compound. It is found in the skin of poison frogs from the genera Dendrobates, Epipedobates, Minyobates, and Phyllobates and toads from the genus Melanophryniscus. Its name comes from the pumiliotoxin family (PTXs) and its molecular mass of 251 daltons. When the toxin enters the bloodstream through cuts in the skin or by ingestion, it can cause hyperactivity, convulsions, cardiac arrest and ultimately death. It is especially toxic to arthropods, even at low concentrations.
Arenobufagin is a cardiotoxic bufanolide steroid secreted by the Argentine toad Bufo arenarum. It has effects similar to digitalis, blocking the Na+/K+ pump in heart tissue.
Convallatoxin is a glycoside extracted from Convallaria majalis.
The tangena ordeal was a form of trial by ordeal practiced in Madagascar to determine the guilt or innocence of an accused party. The trial utilized seeds of the tree species Cerbera manghas, which produces seeds that contain highly toxic cardiac glycosides including cerberin and tanghinin.
Sassywood is an ancient West African form of trial by ordeal. Although it has been outlawed due to human rights concerns, it remains in sporadic use in Liberia. In sassywood, the necessary ordeal can take on many different forms. The principal one involves the drinking of a poisonous concoction made from the bark of the "Ordeal Tree", or erythrophleum suaveolens. Another involves the rubbing of a red-hot machete on the legs of the suspect, while a third involves dipping the suspect's hand into hot oil.
Cassaine is a toxic compound found within the tree genus Erythrophleum. This genus has a range from Senegal to Sudan and Kenya in the east, and south to Zimbabwe and Mozambique. Cassaine was first isolated by the G. Dalma group in 1935 from the Erythrophleum guinneese tree. Since ancient times cassaine has been used as an ordeal poison by African tribes. It has also been utilized extensively as an arrow poison by the Casamance people of Senegal.
Dioscorine is an alkaloid toxin isolated from the tubers of tropical yam on several continents. It has been used as a monkey poison in some African countries, and as an arrow poison to aid in hunting in several parts of Asia. It was first isolated from Dioscorea hirsute by Boorsma in 1894 and obtained in a crystalline form by Schutte in 1897, and has since been found in other Dioscorea species. Dioscorine is a neurotoxin that acts by blocking the nicotinic acetylcholine receptor. Dioscorine is generally isolated in tandem with other alkaloids such as dioscin but is usually the most potent toxin in the mixture. It is a convulsant, producing symptoms similar to picrotoxin, with which it shares a similar mechanism of action.
Calotropin is a toxic cardenolide found in plants in the family Asclepiadoideae. In extreme cases, calotropin poisoning can cause respiratory and cardiac failure. Accidental poisoning is common in livestock who have ingested milkweed. Calotropin is commonly stored as a defense mechanism by insects that eat milkweeds as their main food source.