Coprine

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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.

History

Because of the similarities to

disulfram (tetraethylthiuram disulfide) poisoning, it was long speculated that disulfram was the active ingredient in common inkcap. In 1956 it was reported that disulfram had been isolated from coprinus, but this finding could not be replicated.[5] In 1975, coprine was identified as the compound in the common inkcap, with the mechanism identified in 1979.[6][7][8]

Symptoms

Symptoms of coprine poisoning include facial reddening/flushing,

salivation. [3]: 288  [9] This can be described as the alcohol flush reaction. Symptoms typically arise five to ten minutes after consumption of alcohol. If no more alcohol is consumed, the symptoms will generally subside over two to three hours, and symptom severity is proportional to the amount of alcohol consumed. Consumption of alcohol can induce these symptoms for up to 5 days after ingesting coprine.[9] Interestingly, symptoms of coprine poisoning do not appear when the mushroom is ingested raw, but only when the mushroom is cooked.[5]

In examining coprine poisoning cases in Germany in 2010, none of the patients died, and all made full recoveries after abstaining from alcohol. In one case medical care was not sought at all, and while there was a range in time of ethanol consumption after mushroom consumption, all the cases had well-cooked the mushrooms before ingestion.[10]

The symptoms of coprine poisoning and alcohol consumption are similar to those induced by

reproductive effects, making it ill-suited for long-term use. [12]

Mechanism of action

Coprine

covalent bonding is reversible, which is what allows symptoms to subside if no more alcohol is consumed.[8]

1-Aminocyclopropanol also deactivates the esterase activity of acetaldehyde dehydrogenase, but less significantly.[13]

Synthesis

Coprine is the first discovered compound with a naturally occurring cyclopropanone group.[7] Chemical synthesis can be effectively carried out by conducting an N-acylation reaction on 1-aminocyclopropanol.[7] Treatment of isocyanatocyclopropane with hydrochloric acid leads to the hydrochloride of 1-aminocyclopropanol. Adding sodium hydroxide to create 1-aminocyclopropanol will destabilize the structure, so synthesis must be conducted using the hydrochloride. The addition of the hydrochloride to N-phthaloyl-L-glutamic anhydride will undergo acylation. Lastly, the blocking group is removed using hydrazine, yielding coprine.[7] The enantiomer, isocoprine, is formed in negligible quantities in small-scale synthesis but is synthesized in higher amounts in large-scale, industrial synthesis.[7]

References

  1. ^ RÖMPP Online – Version 3.4, Stuttgart: Thieme Chemistry, 2009
  2. ^ "Disulfiramlike Mushroom Toxicity". Medscape. 2017-01-07.
  3. ^
    ISBN 978-0-7167-2600-5
    .
  4. PMID 1344910
    .
  5. ^
    PMC 1574797
    .
  6. doi:10.1039/C39750000946
    .
  7. ^
    doi:10.1039/P19770000684
    .
  8. ^
    PMID 369602
    .
  9. ^ a b "Mushroom Poisoning Syndromes". North American Mycological Association. Retrieved 23 April 2020.
  10. S2CID 43434106
    .
  11. ^
    PMID 22544865
    .
  12. PMID 1344910
    .
  13. PMID 6870943
    .
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