Α-Amanitin: Difference between revisions
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| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Alpha-amanitin.png|200px|Alpha-amanitin]] |
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Alpha-amanitin-Line-Structure2.png|200px|Alpha-amanitin]] |
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| Other names |
| Other names |
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Revision as of 22:45, 8 October 2006
| Α-Amanitin | |
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| Other names | amanitin, alpha-amanitine, alpha-amatoxin |
| Molecular formula | C39H54N10O14S |
| SMILES | OCC(O)C(C)C(C(NC1C(NCC(NC(C(C)CC)C(NCC(NC (CS(C2=C(C1)C3=C(N2)C=C(O)C=C3)=O)C(NC(CC (N)=O)C(N4C5CC([H])(C4)O)=O)=O)=O)=O)=O)= O)=O)NC5=O |
| Molar mass | 918.971 g/mol |
| CAS number | [23109-05-9] |
| Infobox disclaimer and references | |
Alpha-amanitin or α-amanitin is a cyclic nonribosomal peptide of eight amino acids. It is possibly the most deadly of all the amatoxins, toxins found in the Amanita genus of mushrooms, one being the Death cap, or Amanita phalloides. It is also found in the mushroom Galerina autumnalis, which is nonconformist of the Amanita genus. The oral LD50 of amanitin is approximately 0.1 mg/kg.
Scientific use
Because of the mechanisms that make it a deadly toxin, alpha-amanitin is also used as an inhibitor of RNA polymerase II.[1]
Symptoms of poisoning
Alpha-amanitin has an unusually strong and specific attraction to the enzyme RNA polymerase II. Upon ingestion, it binds to the RNA polymerase II enzyme, effectively causing cytolysis of hepatocytes (liver cells).[2] Few effects are reported within 10 hours; it is not unusual for significant effects to take as much as 24 hours after ingestion, this delay in symptoms making it even more difficult to diagnose as well as dangerous. By then, it is far past the time in which stomach pumping would yield an efficient result. Diarrhea and cramps are the first symptoms, but those pass, giving a false sign of remission. Typically, on the 4th to 5th day, the toxin starts to have severe effects on the liver and kidneys, leading to total system failure in both. Death usually takes place around a week from ingestion.[3]
Around 15% of those poisoned will die in around 10 days progressing through a comatose stage to renal failure, liver failure, hepatic coma, respiratory failure and death. Those who recover are unlikely to regain full health. Diagnosis is difficult, centered around the described clinical symptoms as well as alpha-amanitin content excreted in the urine. Urine screening is highly sensitive but can usually be useful if ingested within the preceding 48 hours. Treatment is mainly supportive (gastric lavage, activated carbon, fluid resuscitation) but includes various drugs to counter the amatoxins, including penicillin and cephalosporin derivatives, and, in cases of greater ingestion, can extend to an orthotopic liver transplant. The most reliable method to treat amanitin poisoning is through having the stomach pumped immediately after ingestion; however, the onset of symptoms is generally too late for this to be an option.