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orellanine
Sign in to saveOrellanine or orellanin is a mycotoxin found in a group of mushrooms known as the Orellani within the family Cortinariaceae. Structurally, it is a bipyridine N-oxide compound somewhat related to the herbicide diquat.
Chemical data
- Formula
- C10H8N2O6
- Molecular weight
- 252.18 g/mol
- IUPAC name
- 2-(1,3-dihydroxy-4-oxo-2-pyridinyl)-1,3-dihydroxypyridin-4-one
- SMILES
- C1=CN(C(=C(C1=O)O)C2=C(C(=O)C=CN2O)O)O
- InChIKey
- JGRNMEQUBVRSQR-UHFFFAOYSA-N
- XLogP
- -1
- Polar surface area
- 122 Ų
- H-bond donors
- 4
- H-bond acceptors
- 8
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 252.038235976
Show 3 more facts
- canonical SMILES
- [O-][n+]1ccc(O)c(O)c1c2[n+]([O-])ccc(O)c2O
- chemical formula
- C₁₀H₈N₂O₆
- Commons category
- Orellanine
Sources (2)
via Wikidata · CC0
~6 min read
Article
9 sectionsContents
- History
- Synthesis
- Structure
- Toxicity
- Treatment
- Research
- See also
- References
- External links
Orellanine or orellanin is a mycotoxin found in a group of mushrooms known as the Orellani within the family Cortinariaceae. Structurally, it is a bipyridine N-oxide compound somewhat related to the herbicide diquat.
==History== Orellanine first came to people's attention in 1952 when a mass poisoning of 102 people in Konin, Poland resulted in 11 deaths. Orellanine comes from a class of mushrooms that fall under the genus Cortinarius, and has been found in the species C. orellanus, rubellus, henrici, rainerensis and bruneofulvus. Poisonings related to these mushrooms have occurred predominately in Europe where mushroom foraging was common, though cases of orellanine poisoning have been reported in North America and Australia as well. There are several reported cases of people ingesting orellanine-containing mushrooms after mistaking them for edible or hallucinogenic mushrooms.