Coprin

Structural formula
General
Surname	Coprin
other names	N 5 - (1-Hydroxycyclopropyl) - L -glutamine; ( S ) -2-Amino-5 - [(1-hydroxycyclopropyl) amino] -5-oxopentanoic acid;
Molecular formula	C 8 H 14 N 2 O 4
Brief description	colorless, crystalline substance
External identifiers / databases
PubChem	108079
ChemSpider	97180
Wikidata	Q1131548
properties
Molar mass	202,21 g · mol -1
Physical state	firmly
Melting point	197-199 ° C
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Coprin is a mushroom poison . It was first found in wrinkled tintling ( Coprinus atramentarius ), and it is also found in mica tinting ( C. micaceus ). Reports that Coprin is also contained in the nettle-stemmed witch's boletus have not been substantiated (see section “Meaning” in the species portrait).

effect

Coprin does not break down into glutamic acid and 1-aminocyclopropanol , the biologically active substance that causes symptoms , until it is heated or when exposed to acid . Therefore, the syndrome should not occur when consuming raw mushrooms. It inhibits (inhibits) the enzyme acetaldehyde dehydrogenase (ALDH). After alcohol consumption, this enzyme works to metabolize the ethanol to acetic acid ; if it is blocked, acetaldehyde accumulates and causes the so-called Coprinus syndrome , better known as acetaldehyde syndrome - in English also known as the disulfiram-like reaction or disulfiram-like syndrome , as disulfiram triggers the same syndrome when alcohol is consumed afterwards. The symptoms of Coprinus syndrome begin with sweating, headache, nausea and vomiting, reddish tinting of the skin on the face and occasionally the skin of the body as well as tingling and a feeling of cold in the arms and legs, and can range up to palpitations, arrhythmias, tightness or collapse. The poison remains in the body for about 24 hours, less often two to five days, so that alcohol consumption is not recommended during this period, as the symptoms would reappear in this case. Coprin is harmless without alcohol.

The wrinkle ink ( Coprinus atramentarius ) contains coprin.
Scheme of the metabolism of Coprin and Coprinus syndrome

literature

L. Matthies, H. Laatsch: Unusual mushroom poisoning: Coprin, an inhibitor of alcohol breakdown. (PDF; 790 kB) In: Pharmacy in our time . No. 21, 1992, pp. 14-20, DOI: 10.1002 / pauz.19920210107 .

Individual evidence

↑ ^a ^b entry on Coprin. In: Römpp Online . Georg Thieme Verlag, accessed on June 1, 2014.
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ Franz-Xaver Reichl: Pocket Atlas of Toxicology . 2nd updated edition. Nikol Verlag, ISBN 978-3-86820-005-8 .
↑ Coprinus Syndrome , described on toxinfo.org (accessed August 28, 2014).
↑ Disulfiram Toxicity Clinical Presentation : Excerpt with causes and symptoms of the syndrome from an article on emedicine.medscape.com (English, accessed on August 28, 2014).
↑ W. Forth, D. Henschler, W. Rummel, Allgemeine und Spezial Pharmakologie und Toxikologie. 3rd edition, BI Wissenschaftsverlag, 1980, ISBN 3-411-01588-8 .

[RÖMPP_Online-1] try on Coprin. In: Römpp Online . Georg Thieme Verlag, accessed on June 1, 2014.

[NV-2] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[3] Franz-Xaver Reichl: Pocket Atlas of Toxicology . 2nd updated edition. Nikol Verlag, ISBN 978-3-86820-005-8 .

[4] Coprinus Syndrome , described on toxinfo.org (accessed August 28, 2014).

[5] Disulfiram Toxicity Clinical Presentation : Excerpt with causes and symptoms of the syndrome from an article on emedicine.medscape.com (English, accessed on August 28, 2014).

[6] W. Forth, D. Henschler, W. Rummel, Allgemeine und Spezial Pharmakologie und Toxikologie. 3rd edition, BI Wissenschaftsverlag, 1980, ISBN 3-411-01588-8 .