Orellanine
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Orellanine
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CAS No:
37338-80-0
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Formula:
C10H8N2O6
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Chemical Name:
Orellanine
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Synonyms:
[2,2′-Bipyridine]-3,3′,4,4′-tetrol,1,1′-dioxide;Orellanine;3,3′,4,4′-Tetrahydroxy-2,2′-bipyridine-1,1′-dioxide;2-(3,4-Dihydroxy-1-oxidopyridin-1-ium-2-yl)-3,4-dihydroxypyridin-1-ium-1-olate
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CAS No:
Safety Information
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a POTW is acceptable only after review by the governing authority. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must meet Hazardous Material Criteria for disposal.
Toxicity
LD50 Mouse ip approx 20 mg/kg|LD50 Mouse ip 12.5 mg/kg|LD50 Mouse oral 90 mg/kg
Orellanine has been found in at least 34 types of mushrooms in the Cortinariaceae family(1). Levels have been reported to range from 0.45% in Cortinarius henrici to 1.1-1.4% in Cortinarius orellanus(1). The compound was found in five Cortinarius from the subgenus Leprocybe, section Orellani(1). Orellanine was also isolated from Cortinarius speciosissimus(2).
Mushrooms of the Cortinarius species are nephrotoxic and can cause severe acute renal failure. The toxic effect is due to orellanine. ... In addition to accidental intoxications as a consequence of mushroom meals, recent cases are often due to voluntary abuse of natural drugs like magic mushrooms. Four cases of acute renal failure from intoxication by Cortinarius species by confusing it with psychoactive fungi are reported. Typical for the Cortinarius poisoning is the long latency period from ingestion until the onset of clinical symptoms (3 - 20 days)(1).
Drug Information
A woman suffering from acute tubulo-interstitial nephritis was admitted to the hospital ten days after deliberate intoxication by ingestion of Cortinarius orellanus. Orellanine, the main toxin responsible for orellanine poisoning, was detected in biological fluids and renal biopsies. It was assayed by direct spectrofluorimetry on two-dimensional thin-layer chromatograms after specific photodecomposition into orelline. The orellanine concentration was 6.12 mg/L in the plasma (10 days after ingestion). Orellanine levels in renal biopsies were 7 ug per 25 cu mm of the first biopsy (13 days after ingestion) and 24 ug per 8 cu mm of the second biopsy (6 months later).
/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
/SIGNS AND SYMPTOMS/ Mushrooms of the ubiquitous Cortinarius species (Cs) contain nephrotoxins that can cause acute and chronic renal failure by an unknown pathomechanism. Typical is a long symptom-free interval before the onset of clinical disease. A causal form of therapy is not known. Early hemodialysis can improve the prognosis of this potentially life-threatening condition. Diagnosis of Cs poisoning can be made by detecting the responsible toxin--orellanine--in plasma or renal tissue by fluorimetry after thin-layer chromatography or by identifying the spores of left-over mushrooms as Cs. Renal histology shows nonspecific changes such as tubular dilatation and flattening of the epithelium and signs of interstitial edema followed by interstitial fibrosis...|/SIGNS AND SYMPTOMS/ The authors present the case reports of a 30-year-old man and his 29-year-old wife who ingested a mushroom meal containing Cortinarius speciosissimus. Features of this intoxication include gastrointestinal symptoms such as nausea, vomiting, and diarrhea as well as back pain. The toxin orellanine is nephrotoxic and can lead to acute renal failure. A long symptom-free interval of 2 to 21 days is characteristic of this poisoning. The diagnosis can be made by mycologic testing or by toxicologic analysis of a renal biopsy specimen. Reported therapeutic options include hemodialysis, plasmapheresis, or drug therapy with corticosteroids, all of which have yielded variable results. Here the authors report the use of antioxidant therapy in 2 patients with acute renal failure caused by Cortinarius speciosissimus intoxication.|/SIGNS AND SYMPTOMS/ Mushrooms of the Cortinarius species are nephrotoxic and can cause severe acute renal failure. The toxic effect is due to orellanine. ... In addition to accidental intoxications as a consequence of mushroom meals, recent cases are often due to voluntary abuse of natural drugs like magic mushrooms. Four cases of acute renal failure from intoxication by Cortinarius species by confusing it with psychoactive fungi /are reported/. Typical for the Cortinarius poisoning is the long latency period from ingestion until the onset of clinical symptoms (3 - 20 days). Diagnosis is based on microscopical identification of the mushroom spores, and detection of the orellanine toxin in leftover mushrooms. In renal biopsy tissue, orellanine is detectable by thin-layer chromaography technique up to 6 months after poisoning. There is no causative therapy, and treatment is symptomatic with adequate hemodialysis. In cases of otherwise unexplained acute renal failure, intoxication with nephrotoxic mushrooms should be considered.|/CASE REPORTS/ Orellanin poisoning is characterized by an acute renal failure which can be lethal if the appropriate treatment is not given. A 31-year old woman was admitted to hospital 10 days after she had deliberately ingested 2 raw carpophores of the mushroom Cortinarius orellanus. Acute renal failure (creatininaemia 1,100 umol/L) developed, requiring 6 sessions of haemodialysis, one of plasmapheresis and the administration of diltiazem and aminoacids. Plasma and tissue assays of orellanin, the mushroom's toxin, were performed by two-dimensional thin layer chromatography. Before hemodialysis and 10 days after ingestion of the poison, the plasma contained orellanin. Eighteen months after the attempted suicide, the plasma creatinine level was 181 umol/L.|For more Human Toxicity Excerpts (Complete) data for Orellanine (9 total), please visit the HSDB record page.
orellanine
Orellanine Use and Manufacturing
Orellanine is a nephrotoxic substance and was isolated from Cortinarius speciosissimus, C. henrici, and C. orellanus ... also found in five Cortinarius from the subgenus Leprocybe, section Orellani.|Orellanine has been found in at least 34 types of mushrooms in the Cortinariaceae family.|Mushrooms of the Cortinarius species are nephrotoxic and can cause severe acute renal failure. The toxic effect is due to orellanine.
Computed Properties
Molecular Weight:252.18
XLogP3:-1
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:1
Exact Mass:252.03823598
Monoisotopic Mass:252.03823598
Topological Polar Surface Area:122
Heavy Atom Count:18
Complexity:507
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
- Hot Searches
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