Coprine

Coprine

Names
IUPAC name N-(1-Hydroxycyclopropyl)-L-glutamine
Other names (S)-2-Amino-5-[(1-hydroxycyclopropyl)amino]-5-oxopentanoate
Identifiers
CAS Number	58919-61-2
ChemSpider	97180
Jmol interactive 3D	Image
PubChem	108079
InChI InChI=1S/C8H14N2O4/c9-5(7(12)13)1-2-6(11)10-8(14)3-4-8/h5,14H,1-4,9H2,(H,10,11)(H,12,13)/t5-/m0/s1 Key: OEEZRBUCLFMTLD-YFKPBYRVSA-N InChI=1/C8H14N2O4/c9-5(7(12)13)1-2-6(11)10-8(14)3-4-8/h5,14H,1-4,9H2,(H,10,11)(H,12,13)/t5-/m0/s1 Key: OEEZRBUCLFMTLD-YFKPBYRVBF
SMILES O=C(NC1(O)CC1)CC[C@@H](C(=O)O)N
Properties
Chemical formula	C8H14N2O4
Molar mass	202.21 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).
Infobox references

Coprine is a mycotoxin. It was first isolated from common inkcap (Coprinopsis atramentaria). It also occurs in other mushrooms in the genus Coprinopsis^[2] and in the brawny bolete (Imperator torsus).^[3]

When combined with the consumption of alcohol, it causes "Coprinus syndrome".^[4]:284[5] Symptoms include facial reddening, nausea, vomiting, malaise, agitation, palpitations and tingling in limbs, and arise five to ten minutes after consumption of alcohol.^[4]:288 The signs are similar to those induced by disulfiram (Antabuse) and subsequent alcohol consumption. If no more alcohol is consumed, the symptoms will generally subside over two or three hours. Symptom severity is proportional to the amount of alcohol consumed.

Coprine is metabolized into glutamic acid and 1-aminocyclopropanol, the biologically active substance which inhibits the enzyme acetaldehyde dehydrogenase. This enzyme is involved in the metabolism of alcohol. When it is blocked, acetaldehyde accumulates causing the adverse reaction.

References

1. RÖMPP Online – Version 3.4, Stuttgart: Thieme Chemistry, 2009
2. "Disulfiramlike Mushroom Toxicity". Medscape.
3. Kiwitt U, Laatsch H. (1994). "Coprin in Boletus torosus: Beruht die angebliche Alkoholunverträglichkeit durch den Verzehr des Netzstieligen Hexenröhrlings (Boletus luridus) auf einer Verwechslung?" [Coprine in Boletus torosus: Is the alleged alcohol hypersensitivity by ingestion of B. luridus caused by a mistake?] (PDF). Zeitschrift für Mykologie (in German) 60 (2): 423–30.
4. Benjamin, Denis R. (1995). Mushrooms: poisons and panaceas—a handbook for naturalists, mycologists and physicians. New York: WH Freeman and Company. ISBN 0-7167-2600-9.
5. Michelot, D. (1992). "Poisoning by Coprinus atramentarius". Natural toxins 1 (2): 73–80. doi:10.1002/nt.2620010203. PMID 1344910.