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{{Short pages monitor}}<!-- This long comment was added to the page to prevent it from being listed on Special:Shortpages. It and the accompanying monitoring template were generated via Template:Long comment. Please do not remove the monitoring template without removing this comment as well.-->
{{chembox
| ImageFile = Erythrophleine structure.png
| ImageSize =
| ImageAlt =
| IUPACName = (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
| OtherNames = {{Unbulleted list
| Norcassamidine
}}
| Name = Erythrophleine<ref>{{cite web |url=https://pubchem.ncbi.nlm.nih.gov/compound/76961570|title=Erythrophleine|website= PubChem|publisher= NIH}}</ref>
|Section1 = {{Chembox Identifiers
| CASNo = 36150-73
| CASNo_Ref = {{cascite|correct|CAS}}
| PubChem = 76961570
}}
|Section2 = {{Chembox Properties
| C=24 | H=39 | N=1| O=5
| MolarMass = 421.6 g/mol
| Appearance = White, crystalline powder
| Density =
| MeltingPt = 115
| BoilingPt =
| Solubility = Miscible
}}
}}

'''Erythrophleine''' is a complex [[alkaloid]] and [[ester]] of tricyclic [[diterpene | diterpene acids]] derived from many of the plants in the genus [[erythrophleum]].<ref name="NIHEncyclopedia">{{cite web |url=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9771672/|title=PubMed Central|author=<!--Not stated--> |date= |website=National Library of Medicine |publisher=NIH |access-date= |quote=}}</ref> A highly toxic compound, it is most commonly known for its use in West African [[trials by ordeal]].<ref name=pri>{{cite web|url=http://www.pri.org/theworld/?q=node/8251|title=Liberian Justice System|publisher=PRI|date=February 22, 2007}}</ref> Exposure to erythrophleine can quickly lead to [[ataxia]], [[dyspnea]], heart paralysis, and sudden death. Visible effects of erythrophleine poisoning include induced [[panic| terror]], labored and irregular breathing, [[convulsions]], urination, and vomiting.<ref name="HarvardHerbaria">{{cite web |url=https://www.jstor.org/stable/pdf/41762174.pdf |title=The Ordeal Poisons of Madagascar and Africa|last=Robb |first=George |date= March 18, 1957|publisher=Harvard University Herbaria}}</ref>

==Mechanism of Action==

Once ingested, erythrophleine primarily acts on the body by disrupting the [[nervous system]]. It does this by inhibiting [[sodium-potassium pump | Na-K ATPase]], an enzyme that breaks down [[ATP]] to generate an [[electric potential]] by moving sodium and potassium ions against their [[concentration gradient]].<ref name="pmid33716756">{{cite journal | vauthors=Gagnon KB, Delpire E| title=Sodium Transporters in Human Health and Disease (Figure&nbsp;2) | journal=[[Frontiers Media#List of journals|Frontiers in Physiology]] | volume=11 | pages=588664 | year=2021 | doi = 10.3389/fphys.2020.588664 | pmc=7947867 | pmid=33716756 | doi-access=free }}</ref> 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.<ref>{{cite web |url=https://www.sciencedirect.com/science/article/abs/pii/0006295264900747 |title=Studies of odium-potassium activated adenosine triphosphatase: VII-inhibition by erythrophleum alkaloids |last=Bonting |first=Sjoerd |date=January 1964|publisher=Biochemical Pharmacology}}</ref> This can have a number of compounding effects including weakened nerve signaling responses and inhibited ability to maintain cellular [[homeostasis]].<ref>{{Cite web|url=http://cvpharmacology.com/cardiostimulatory/digitalis|title=CV Pharmacology {{!}} Cardiac Glycosides (Digitalis Compounds)|website=cvpharmacology.com|access-date=2017-06-08}}</ref>

While the exact [[reaction mechanism | mechanism]] of this process is unknown, it is likely similar to that of [[cardiac glycosides]].<ref>{{cite web |url=https://books.google.com/books?id=T4O0fQdMqHMC&pg=PA19&lpg=PA19&dq=Erythrophleine&source=bl&ots=8RvxjkjF1C&sig=ACfU3U1RpDwPrC1eD8eDqhuMYSEQvB5jOg&hl=en&sa=X&ved=2ahUKEwiRnIGIrfyFAxVyEFkFHUxpAP84ChDoAXoECAIQAw#v=onepage&q=Erythrophleine&f=false |title=Metabolic Inhibitors: A Comprehensive Treatise |last=Hochster |first=R |date=1972|publisher=Academic Press}}</ref> 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.<ref name=Pate2016>{{cite journal | vauthors = Patel S | title = Plant-derived cardiac glycosides: Role in heart ailments and cancer management | journal = Biomedicine & Pharmacotherapy | volume = 84 | pages = 1036–1041 | date = December 2016 | pmid = 27780131 | doi = 10.1016/j.biopha.2016.10.030 }}</ref> The most well-known of these molecules is the active toxin in [[foxglove]].<ref>{{cite journal | vauthors = Riganti C, Campia I, Kopecka J, Gazzano E, Doublier S, Aldieri E, Bosia A, Ghigo D | display-authors = 6 | title = Pleiotropic effects of cardioactive glycosides | journal = Current Medicinal Chemistry | volume = 18 | issue = 6 | pages = 872–885 | date = 2011-01-01 | pmid = 21182478 | doi = 10.2174/092986711794927685 }}</ref>


==Use as an Ordeal Poison==

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 Africa | West African]] states, ordeal trials still take place with some regularity.<ref>{{cite web |url= https://www.voanews.com/a/a-13-2006-10-27-voa19/398774.html|title= Controversial Practices: Trial by Ordeal in Liberia|date= October 10, 2009|website= VOA|publisher=VOA News}}</ref> Some prominent economists have even argued that sassywood is a more effective substitute to [[Liberia | Liberian]] courts, given the decrepit nature of the country's judicial system.<ref>{{cite web |url=https://www.peterleeson.com/Sassywood.pdf |title= Sassywood|last=Leeson |first= Peter|date= February 15, 2012|publisher=Journal of Comparative Economics}}</ref>

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.<ref name="HarvardHerbaria"></ref> 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.<ref name="Society1850">{{cite book |title=The ... Annual Report of the American Colonization Society ... |url=https://books.google.com/books?id=1kksAAAAYAAJ&pg=RA5-PA39 |year=1850 |publisher=The Society |pages=39–40}}</ref>

== References ==

Revision as of 20:49, 13 May 2024

Template:New user article

Erythrophleine[1]
Names
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
  • Norcassamidine
Identifiers
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]

Mechanism of Action

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]


Use as an Ordeal Poison

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]

References

  1. ^ "Erythrophleine". PubChem. NIH.
  2. ^ "PubMed Central". National Library of Medicine. NIH.
  3. ^ "Liberian Justice System". PRI. February 22, 2007.
  4. ^ a b Robb, George (March 18, 1957). "The Ordeal Poisons of Madagascar and Africa" (PDF). Harvard University Herbaria.
  5. ^ Gagnon KB, Delpire E (2021). "Sodium Transporters in Human Health and Disease (Figure 2)". Frontiers in Physiology. 11: 588664. doi:10.3389/fphys.2020.588664. PMC 7947867. PMID 33716756.
  6. ^ Bonting, Sjoerd (January 1964). "Studies of odium-potassium activated adenosine triphosphatase: VII-inhibition by erythrophleum alkaloids". Biochemical Pharmacology.
  7. ^ "CV Pharmacology | Cardiac Glycosides (Digitalis Compounds)". cvpharmacology.com. Retrieved 2017-06-08.
  8. ^ Hochster, R (1972). "Metabolic Inhibitors: A Comprehensive Treatise". Academic Press.
  9. ^ Patel S (December 2016). "Plant-derived cardiac glycosides: Role in heart ailments and cancer management". Biomedicine & Pharmacotherapy. 84: 1036–1041. doi:10.1016/j.biopha.2016.10.030. PMID 27780131.
  10. ^ Riganti C, Campia I, Kopecka J, Gazzano E, Doublier S, Aldieri E, et al. (2011-01-01). "Pleiotropic effects of cardioactive glycosides". Current Medicinal Chemistry. 18 (6): 872–885. doi:10.2174/092986711794927685. PMID 21182478.
  11. ^ "Controversial Practices: Trial by Ordeal in Liberia". VOA. VOA News. October 10, 2009.
  12. ^ Leeson, Peter (February 15, 2012). "Sassywood" (PDF). Journal of Comparative Economics.
  13. ^ The ... Annual Report of the American Colonization Society ... The Society. 1850. pp. 39–40.
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