Coprine

Coprine
Names
IUPAC name
N5-(1-Hydroxycyclopropyl)-L-glutamine
Systematic IUPAC name
(2S)-2-Amino-5-[(1-hydroxycyclopropyl)amino]-5-oxopentanoic acid
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • 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
  • O=C(NC1(O)CC1)CC[C@@H](C(=O)O)N
Properties
C8H14N2O4
Molar mass 202.210 g·mol−1
Melting point 197 to 199 °C (387 to 390 °F; 470 to 472 K)
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 occurs in mushrooms in the genus Coprinopsis, specifically within sections Alopeciae, Atramentariae, and Picaceae. When combined with alcohol, it causes "Coprinus syndrome". 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.

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