coprine
Sign in to saveAlso known as (2S)-2,5-diamino-5-oxopentanoic acid, N(5)-(1-hydroxycyclopropyl)-L-glutamine, L-coprine, coprin
Coprine is a mycotoxin. It was first isolated from common inkcap (Coprinopsis atramentaria). It occurs in mushrooms in the genus Coprinopsis, specifically within sections Alopeciae, Atramentariae, and Picaceae. When combined with alcohol, it causes "Coprinus syndrome". It inhibits the enzyme aldehyde dehydrogenase, which is involved in the metabolism of alcohol. This inhibition leads to a buildup of acetaldehyde, causing an alcohol flush reaction. Because of this, the mushroom is commonly referred to as '''Tippler's Bane.'''
Wikidata facts
- Mass
- 202.095
Show 4 more facts
- chemical formula
- C₈H₁₄N₂O₄
- canonical SMILES
- C1CC1(NC(=O)CCC(C(=O)O)N)O
- isomeric SMILES
- C1CC1(NC(=O)CC[C@@H](C(=O)O)N)O
- Commons category
- Coprine
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Article
5 sectionsContents
- History
- Symptoms
- Mechanism of action
- Synthesis
- References
Coprine is a mycotoxin. It was first isolated from common inkcap (Coprinopsis atramentaria). It occurs in mushrooms in the genus Coprinopsis, specifically within sections Alopeciae, Atramentariae, and Picaceae. When combined with alcohol, it causes "Coprinus syndrome". It inhibits the enzyme aldehyde dehydrogenase, which is involved in the metabolism of alcohol. This inhibition leads to a buildup of acetaldehyde, causing an alcohol flush reaction. Because of this, the mushroom is commonly referred to as '''Tippler's Bane.'''
==History== Because of the similarities to disulfram (tetraethylthiuram disulfide) poisoning, it was long speculated that disulfram could actually be produced by fungi. In 1956 it was reported that disulfram had been isolated from coprinus, but this finding could not be replicated. In 1975, coprine was identified as the compound in the common inkcap, with the mechanism identified in 1979.