{{Chembox |ImageFile = Ichthyothereol skeletal.png |PIN = (2''S'',3''R'')-2-[(1''E'')-Non-1-ene-3,5,7-triyn-1-yl]oxan-3-ol |OtherNames = (−)-Ichthyothereol, Cunaniol |Section1 = {{Chembox Identifiers |CASNo = 2294-61-3 |CASNo_Ref = {{cascite|correct|CAS}} |UNII_Ref = {{fdacite|correct|FDA}} |UNII = 6VLN4U8PSW |PubChem = 6451387 |ChemSpiderID = 4953853 |ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |SMILES = CC#CC#CC#C/C=C/[C@H]1[C@@H](CCCO1)O |InChI = InChI=1S/C14H14O2/c1-2-3-4-5-6-7-8-11-14-13(15)10-9-12-16-14/h8,11,13-15H,9-10,12H2,1H3/b11-8+/t13-,14+/m1/s1 }} |Section2 = {{Chembox Properties |C=14 | H=14 | O=2 }} }}
'''Ichthyothereol''' is a toxic polyyne compound found in the leaves and flowers of several plants in South and Central America. These plant sources and their extracts are known for their toxic effects on fish, and have long been used by various native tribes in the lower Amazon basin for fishing.<ref name=JOCFirstTotal/><ref name=Harmata>{{cite book |title= Strategies And Tactics in Organic Synthesis |volume= 6 |editor-last= Harmata |editor-first= Michael |publisher= Elsevier |year= 2005 |pages= 223–229 |chapter= 7. Total Synthesis Based on Alkyne–Co<sub>2</sub>(CO)<sub>6</sub> Complexes. III. First Total Synthesis of (–)-Ichthyothereol |last= Mukai |first= Chisato }}<!-- this 2005 ref is a secondary by same author as 2001 actual total-synthesis, highlighting their general approach and notability of it as an example --></ref> The name of the genus ''Ichthyothere'', the members of which contain noticeable amounts of the natural product in their leaves, literally translates as ''fish poison.'' It is so toxic, fish will jump out of the water if ''Ichthyothere terminalis'' leaves are used as bait.{{citation needed|date=February 2016}}<!-- statement imported from Ichthyothere and polyacetylene, where it was not cited --> This chemical is also found in the leaves and flowers of ''Dahlia coccinea''. The actual chemical was isolated by several different groups and its full chemical structure determined in 1965.<ref name=JOCFirstTotal/> The first total synthesis was published in 2001.<ref name=JOCFirstTotal>{{cite journal |title= First Total Synthesis of (−)-Ichthyothereol and Its Acetate |first1= Chisato |last1= Mukai |first2= Naoki |last2= Miyakoshi |first3= Miyoji |last3= Hanaoka |journal= J. Org. Chem. |year= 2001 |volume= 66 |issue= 17 |pages= 5875–5880 |doi= 10.1021/jo0104532 |pmid= 11511265 }}</ref>
It is also toxic to mice and dogs, producing convulsant effects that are similar to those of picrotoxin.<ref name="CasconMors1965">{{cite journal|last1=Cascon|first1=Seiva C.|last2=Mors|first2=Walter B.|last3=Tursch|first3=Bernard M.|last4=Aplin|first4=Robin T.|last5=Durham|first5=Lois J.|title=Ichthyothereol and Its Acetate, the Active Polyacetylene Constituents of ''Ichthyothere terminalis'' (Spreng.) Malme, a Fish Poison from the Lower Amazon|journal=Journal of the American Chemical Society|volume=87|issue=22|year=1965|pages=5237–5241|issn=0002-7863|doi=10.1021/ja00950a044|pmid=5844817 |bibcode=1965JAChS..87.5237C }}</ref>
== References == {{reflist}}
Category:Convulsants Category:Plant toxins Category:Tetrahydropyrans Category:Polyynes Category:Conjugated enynes Category:Secondary alcohols