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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)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Coprine is a mycotoxin. It was first isolated from common inkcap (Coprinopsis atramentaria). It occurs in mushrooms in the genera Coprinopsis.[2] When combined with alcohol, it causes "Coprinus syndrome".[3]: 284 [4] It inhibits the enzyme acetaldehyde 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.

  1. ^ RÖMPP Online – Version 3.4, Stuttgart: Thieme Chemistry, 2009
  2. ^ "Disulfiramlike Mushroom Toxicity". Medscape. 2017-01-07.
  3. ^ Benjamin, Denis R. (1995). Mushrooms: poisons and panaceas—a handbook for naturalists, mycologists and physicians. New York: WH Freeman and Company. ISBN 978-0-7167-2600-5.
  4. ^ Michelot, D. (1992). "Poisoning by Coprinus atramentarius". Natural Toxins. 1 (2): 73–80. doi:10.1002/nt.2620010203. PMID 1344910.
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