Coprine
From Wikipedia, the free encyclopedia
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| Names | |
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| IUPAC name
N5-(1-Hydroxycyclopropyl)-L-glutamine | |
| Systematic IUPAC name
(2S)-2-Amino-5-[(1-hydroxycyclopropyl)amino]-5-oxopentanoic acid | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C8H14N2O4 | |
| Molar mass | 202.210 g·mol−1 |
| Melting point | 197 to 199 °C (387 to 390 °F; 470 to 472 K)[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Coprine is a toxin. It was first isolated from common inkcap (Coprinopsis atramentaria). It occurs in mushrooms in the genus Coprinopsis,[2] specifically within sections Alopeciae, Atramentariae, and Picaceae. When combined with alcohol, it causes "Coprinus syndrome".[3]: 284 [4] 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.
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.[5] In 1975, coprine was identified as the compound in the common inkcap, with the mechanism identified in 1979.[6][7][8]
Symptoms
Symptoms of coprine poisoning include facial reddening/flushing, nausea, vomiting, malaise, agitation, palpitations, tingling in limbs, and sometimes headache and excessive salivation.[3]: 288 [9] This can be described as the alcohol flush reaction. Symptoms typically arise five to ten minutes after consumption of alcohol. If no more alcohol is consumed, the symptoms will generally subside over two to three hours, and symptom severity is proportional to the amount of alcohol consumed. Consumption of alcohol can induce these symptoms for up to 5 days after ingesting coprine.[9] Interestingly, symptoms of coprine poisoning do not appear when the mushroom is ingested raw, but only when the mushroom is cooked.[5]
In examining coprine poisoning cases in Germany in 2010, none of the patients died, and all made full recoveries after abstaining from alcohol. In one case medical care was not sought at all, and while there was a range in time of ethanol consumption after mushroom consumption, all the cases had well-cooked the mushrooms before ingestion.[10]
The symptoms of coprine poisoning and alcohol consumption are similar to those induced by disulfiram (marketed as Antabuse), a drug utilized to treat chronic alcoholism by inducing severe side-effects to alcohol consumption. Because of this, research was done into the use of coprine as a similar drug for alcoholism.[11] However, testing has shown coprine to have long-term mutagenic and reproductive effects, making it ill-suited for long-term use.[12]
