Common Inkcap (Coprinopsis atramentaria aka Coprinus atramentarius) [but not
Shaggy Inkcap] has within it a sulfur-containing
non-proteinogenic amino acid (NPAA) called
coprine, named after the Genus Coprinus of these mushrooms. Coprine, or N5-1-hydroxycyclopropyl-L-glutamine, metabolises in the body to 1-aminocyclopropanol, which also has the same poisonous effects on the body when consumed with alcohol.
After imbibing alcohol, normally, the enzyme alcohol dehydrogenase-2 (ALDH-2) which is within the body metabolises alcohol to dangerously poisonous Acetaldehyde. But the acetaldehyde, is, in its turn, metabolised by the enzyme acetaldehyde dehydrogenase-2 which converts the acetaldehyde to the mostly-harmless acetic acid (vinegar).
But if Common Inkcap mushrooms were consumed either side of 24 hours of consuming alcohol, the
coprine within the mushrooms prevents the enzyme acetaldehyde dehydrogenase-2 (which is found within Mitochondrial Organelles) from metabolising acetaldehyde to acetic acid. The result is an increase in the very harmful acetaldehyde, which is the cause of hangovers in the first place. Consuming alcohol and coprine within a day or two gives the imbiber an almost instant and severe hangover. Harmless in itself, coprine is poisonous if the mushroom is ingested during or within 24 hours of having partaken of any alcoholic drink.
Alcohol and Common Inkcap, taken together, also prevent the normal breakdown of the neuro-transmitter Dopamine. This results in an excess of this neurotransmitter within the body, leading to very un-pleasant symptoms such as high anxiety, restlessness and high blood pressure.
ANTABUSE / DISULFIRAM
Disulfiram was an artificial pharmaceutical manufactured to treat parasitic infestations. It is a dimer and consists of two identical units stuck back-to-back and has four atoms of sulfur. It was discovered accidentally that Disulfiram also has the same poisonous effect on the human body as does coprine if alcohol is consumed.
This co-effect is so strong that disulfiram is now marketed as the drug variously known as Disulfiram or Antabuse to prevent alcoholics from drinking, for if they do, then they experience these extremely un-pleasant and very dangerous side effects; acetaldehyde is a poison. The net effect is that anyone on the drug will not be able to drink alcohol for several days afterwards.
Forty percent of East Asians have a faulty version of the gene that is responsible for producing ALDH-2, which goes on to construct a mutant version of ALDH-2 called ALDH-2* which fails to catalyse the destruction of acetaldehyde, inflicting upon them an inherited form of severe alcohol intolerance (Asian Flush) similar in effects to that caused by Coprine or Disulfiram.
On the other hand, 25% of drinkers (including the author) are resistant to hangovers; for they metabolise alcohol and acetaldehyde differently. For people in this category, eating Common Inkcap or being given Disulfiram is unlikely to make drinking an unpleasant experience.
A new medicinal use has been found for the pharmaceutical Antabuse (aka Disulfiram): to treat patients with the brain cancer called 'glioblastoma' where otherwise only about 27% of patients diagnosed with the illness survive a year or more. Antabuse, when co-administered with the (fluorine-containing) pharmaceutical gemcitabine (neither of which happen to contain copper), kills cancer infected brain cells by overloading them with copper. Glioblastoma multiforme (GBM) cells tend to have elevated levels of copper anyway, and the additional copper load contributed by the disulfiram/gemcitabine combination overloads the cancerous cell with copper, killing them whilst leaving healthy cells alone.
However, Disulfiram is not without side effects of its own. Disulfiram breaks down in the liver to form Tryptophol which is a sleep-inducing compound. Tryptophol is also produced by the Trypanosomal parasite which gives rise to the condition called 'Sleeping Sickness'. The production of Tryptophol also occurs during secondary fermentation processes such as those used in the production of wine, where it is also found. Thus wine can make you sleepy because of the Tryptophol within it. Tryptophol is chemically similar to Tryptamine, but the -OH substitutes the NH2. Indeed, Tryptamine is the precursor of Tryptophol: when yeast attacks the naturally occurring Tryptamine (an indole amine) in the secondary fermentation process, it replaces the NH2 group with the -OH group whilst at the same time giving off carbon dioxide.