3.5.1 Mushrooms Producing Coprine

During autumn (fall), mushrooms with egg-shaped, grey-white fruiting bodies occasionally appear, very often on road-sides, which after a few days deliquesce into an ink-colored liquid. The mushroom, Coprinus atramentarius, or inky cap, is edible when young, but can cause alcohol incompatability when consumed before, or together with, ethanol.

3.5.2 Chemistry and Action

The offending toxin is a conjugate of cyclopropanone and glutamine, called coprin (Figure 3.4a). In the liver, the amidohemiketal is cleaved into glutamine and cyclopropanone (Figure 3.4b), regarded as the toxic species. Its activity is understood as blocking the enzyme acetaldehyde dehydrogenase by reacting with the essential SH-group in the enzyme with formation of a hemi-thioketal (Figure 3.4c). As a consequence, acetaldehyde, the toxic metabolite of alcohol, will accumulate in the body.

3.5.3 Symptoms and Treatment

The symptoms are described as similar to those observed after application of disulfiram (Antabus), a drug used to discourage alcoholics from drinking. Typical symptoms include flashes, mydriasis, paraesthesia, tachycardia, and sweating, beside nausea and occasionally vomiting. This syndrome is brief in duration and will usually disappear after three to four hours, but may linger up to twenty-four hours.

Figure 3.4 Structures of (a) coprin, (b) cyclopropanone, and (c) the thio-hemiketal of cyclopropanone formed at the essential SH-group of acetaldehyde dehydrogenase that blocks the activity of the enzyme.

The majority of reported cases have shown relatively mild and short-lived toxicity; therefore, in general, supportive care is regarded as the adequate treatment.

3.6 psilocybin and psilocin

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