# Cassaine

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> Markdown URL: https://mediated.wiki/source/Cassaine.md
> Source: https://en.wikipedia.org/wiki/Cassaine
> Source revision: 1308173219
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{{Chembox
| ImageFile = Cassaine.svg
| ImageSize = 200px
| ImageAlt = 
| IUPACName = 2-(Dimethylamino)ethyl [13(15)''E'']-3β-hydroxy-14α-methyl-7-oxo-17-norpimar-13(15)-en-16-oate
| SystematicName = 2-(Dimethylamino)ethyl (''E'')-[(1''R'',4a''S'',4b''R'',7''S'',8a''R'',10a''S'')-7-hydroxy-1,4b,8,8-tetramethyl-10-oxododecahydrophenanthren-2(1''H'')-ylidene]acetate
| OtherNames = 
| Section1 = {{Chembox Identifiers
| CASNo = 468-76-8
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = PQK203C49T
| CASNo_Ref = {{cascite|correct|CAS}}
| PubChem=5281267
|  SMILES=C[C@@H]\1[C@H]2[C@H](CC/C1=C\C(=O)OCCN(C)C)[C@]3(CC[C@@H](C([C@@H]3CC2=O)(C)C)O)C
|  StdInChI=1S/C24H39NO4/c1-15-16(13-21(28)29-12-11-25(5)6)7-8-17-22(15)18(26)14-19-23(2,3)20(27)9-10-24(17,19)4/h13,15,17,19-20,22,27H,7-12,14H2,1-6H3/b16-13+/t15-,17-,19-,20-,22-,24+/m0/s1
|  StdInChIKey=GMHWATCMBXIANN-IOJUAHGHSA-N
| ChemSpiderID = 4444673
| ChEBI = 3454
  }}
| Section2 = {{Chembox Properties
| C=24|H=39|N=1|O=4
| Appearance = 
| Density = 
| MeltingPt = 
| BoilingPt = 
| Solubility = 
  }}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
  }}
}}

'''Cassaine''' is a toxic compound found within the [tree](/source/tree) genus ''[Erythrophleum](/source/Erythrophleum)''. This genus has a range from [Senegal](/source/Senegal) to [Sudan](/source/Sudan) and [Kenya](/source/Kenya) in the east, and south to [Zimbabwe](/source/Zimbabwe) and [Mozambique](/source/Mozambique). Cassaine was first isolated by the G. Dalma group in 1935 from the ''[Erythrophleum guinneese](/source/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](/source/Casamance) people of [Senegal](/source/Senegal).<ref name= Neuwinger >{{cite book | author = Neuwinger, D. Hans | url = https://books.google.com/books?id=_j8ueEmakD0C | title = African Ethnobotany: Poisons and Drugs: Chemistry Pharmacy, Toxicology | access-date = 30 April 2015| isbn = 9783826100772 | year = 1996 | publisher=CRC Press }}</ref>

== Structure ==
The structure of cassaine and other [alkaloid](/source/alkaloid)s found within the genus ''[Erythrophleum](/source/Erythrophleum)'' are similar to the structure of [cardiac glycoside](/source/cardiac_glycoside)s.<ref name= Neuwinger/> This similarity to [cardiac glycoside](/source/cardiac_glycoside)s accounts for the similarity in cardiac activity between cassaine and compounds such as [digitoxin](/source/digitoxin).<ref name= Neuwinger/>  Generally, the structure of cassaine and other ''Erythrophleum'' derivatives are considered ''N''-alkylaminoethyl esters of tricyclic diterpene acids containing a perhydrophenanthrene skeleton.<ref name= Neuwinger/>

== Mechanism of action ==

Cassaine's biological function stems from its ability to interact with Na<sup>+</sup>-K<sup>+</sup> ATPase through its [cardiotonic](/source/cardiotonic) [steroid](/source/steroid) binding site. The binding of cassaine to this site inhibits [ATPase](/source/ATPase). Cassaine can be defined as a specific [inhibitor](/source/Enzyme_inhibitor) of monovalent cation transport and of Na<sup>+</sup>-K<sup>+</sup> ATPase; the result being an [inotropic](/source/inotropic) effect on cardiac muscle.<ref>Tobin, T., Akera, T., Brody, S., Davie, Ku., Brody, T. [https://www.researchgate.net/publication/23010245_Cassaine_mechanism_of_inhibition_of_Na_K_-ATPase_and_relationship_of_this_inhibition_to_cardiotonic_actions "Cassaine: Mechanism of Inhibition of Na+ K+ ATPase and Relationship of this Inhibition to Cardiotonic Actions"], Retrieved on 30 April 2015.</ref>

== Toxicity ==

Cassaine is highly [toxic](/source/toxic) because it acts strongly on the function of the heart by affecting Na<sup>+</sup>-K<sup>+</sup> ATPase.<ref>Maling, H., Krayer, O. [http://jpet.aspetjournals.org/content/86/1/66 "The Action of the Erythrophleum Alkaloids Upon the Isolated Mammalian Heart"], Retrieved on 30 April 2015.</ref> High doses can cause blood pressure problems, [bradycardia](/source/bradycardia), violent fits of [vomiting](/source/vomiting), [arrhythmia](/source/Heart_arrhythmia), and death.
While used widely in Africa for various reasons, cassaine is usually utilized with other alkaloidal compounds from its parent tree. Since mixtures are usually used it is hard to directly gauge its [toxicity](/source/toxicity) from the use of these mixtures. Despite the difficulty, Some examples of the toxicity of several mixtures are available. For instance, the arrow poison used by the [Casamance](/source/Casamance) people of [Senegal](/source/Senegal); it was found by that any hunter who accidentally cut themselves with a poisoned broad-head was seen to die soon, after violent fits of [vomiting](/source/vomiting).<ref name= Neuwinger/>

{| class="wikitable"
|-
! Animal !! {{LD50}} (mg cassaine per kg body mass)
|-
| [Guinea pig](/source/Guinea_pig) || 2.64
|-
| Cat || 1.70
|-
| Rat || 7.2
|-
| Mouse || 2.05
|}<ref name= Neuwinger/>

The lack of widespread use and research in the [western world](/source/western_world) has resulted in the a lack of information with regards to how toxic is to the human body.

== Uses ==

===Ordeal poison===

[Native Africans](/source/Native_Africans) have used cassaine and mixtures containing cassaine as an [ordeal poison](/source/ordeal_poison) for hundreds of years. These uses included trials for supposed [witches](/source/witches) and [warlocks](/source/warlocks). Cassaine was also used for mass cleansings after [epidemic](/source/epidemic)s, wars, natural disasters, etc. Anything that could have been deemed the work of evil forces brought about by an evil person could have brought an [ordeal trial](/source/ordeal_trial) and the use of cassaine. Cassaine use as an ordeal poison caused nearly 2,000 deaths in 1912 [reference]. To this day cassaine is still used in Africa as an ordeal poison.<ref name= Neuwinger/>

===Traditional medicine===

Cassaine and the other alkaloids from ''[Erythrophleum](/source/Erythrophleum)'' were used on many occasions by [native Africans](/source/native_Africans) to treat a variety of ailments. Some of these ailments were [headaches](/source/headaches), heart problems, and [migraines](/source/migraines). Cassaine was also used as a strong local [anesthetic](/source/anesthetic), [diuretic](/source/diuretic), and as an antidote for the swallowing of other poisonous substances due to its powerful [emetic](/source/emetic) effects. Prior to and until the 1930s, cassaine and its partner alkaloids were used as local anesthetics in dental and ophthalmic procedures.<ref name= Neuwinger/>

== Synthesis ==

Cassaine can be prepared by [organic synthesis](/source/organic_synthesis).  One method starting from [carvone](/source/carvone) uses anionic polycyclization as a key step.<ref>{{cite journal | doi = 10.1021/ol4030937 | title = Total Synthesis of (+)-Cassaine Utilizing an Anionic Polycyclization Strategy | date = 2013 | last1 = Ravindar | first1 = Kontham | last2 = Caron | first2 = Pierre-Yves | last3 = Deslongchamps | first3 = Pierre | journal = Organic Letters | volume = 15 | issue = 24 | pages = 6270–6273 | pmid = 24295200 }}</ref>
:thumb|300px|left|One synthesis method for cassaine. A cardiac poison found within some African trees.{{clear-left}}

==References==
{{Reflist|colwidth=30em}}

Category:Alkaloids
Category:Plant toxins

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Adapted from the Wikipedia article [Cassaine](https://en.wikipedia.org/wiki/Cassaine) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Cassaine?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.