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 genera Coprinopsis. When combined with alcohol, it causes "Coprinus syndrome".: 284  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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