Coprine - Why you sometimes don't want to pair a wine with a mushroom dish

  • a rare amino acid (derivative of glutamic acid, natch) present in several edible species of mushroom belonging to the genus Coprinus ("inky caps") including the common ink cap (Coprinus atramentarius), a lawn mushroom that is, most unexpectedly, fairly common
  • is thought that it or one of it's metabolites (cyclopropanone hydrate) inhibits the enzyme aldehyde dehydrogenase (ALDH)
    • alcohol (ethanol) is primarily metabolized in the body by the enzyme alcohol dehydrogenase (ADH) into acetaldehyde, a fairly toxic substance that is responsible for many of the symptoms of a hangover
    • acetaldehyde is then further metabolized by ALDH into not nearly as toxic acetic acid, the stuff in vinegar that makes it taste and smell the delightful way that it does
    • inhibition of ALDH results in the accumulation of acetaldehyde when alcohol is consumed, essentially giving you an insta-hangover
  • gettin' smashed or even just having a single drink up to 72 hours after eating mushrooms containing coprine will cause acetaldehyde poisoning, symptoms of which include flushing, nausea and vomiting, headache, and palpitations
    • symptoms usually only last 2-4 hours but may last up to 2 days (yay!)
    • the same reaction is seen in individuals who: (a) are taking disulfiram (Antabuse), an anti-drinking drug used in the treatment of alcohol dependence (alcoholism) that inhibits ALDH or (b) possess a super effective form of ADH and/or a crappy form of ALDH due to variation in the genes that encode these enzymes (these people are often of East Asian descent)
  • has no known toxic effects on its own - is only poisonous when ingested prior to alcohol consumption, and even then it is the metabolized alcohol that is causing the problems
Berger KJ, Guss DA. Mycotoxins revisited: Part II. J Emerg Med. 2005 Feb;28(2):175-83.

1 chemically inspired comments:

Ozimandius said...

Just thought I'd let you know, the AntiBiotic Metronidazole (commonly used for anaerobic bacteria) has a very similar effect as Antabuse. From what I understand, they are related chemicals (but I may be wrong).