muscarine

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Muscarine
IUPAC name	2,5-anhydro-1,4,6-trideoxy-6-(trimethylammonio)-D-ribo-hexitol
Other names	L-(+)-muscarine, muscarin, (2S,4R,5S)-(4-hydroxy-5-methyl-tetrahydrofuran-2-ylmethyl)-trimethyl-ammonium
Identifiers
CAS number	300-54-9
SMILES	O[C@@H]1C[C@@H](C[N+](C)(C)C)O[C@H]1C
Properties
Molecular formula	C9H20NO2+
Molar mass	174.26 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Amanita muscaria

Muscarine, L-(+)-muscarine, or muscarin is a natural product found in certain mushrooms, particularly in Inocybe and Clitocybe species, such as the deadly C. dealbata. It was first isolated from Amanita muscaria in 1869. It was the first parasympathomimetic substance ever studied and causes profound activation of the peripheral parasympathetic nervous system that may end in convulsions and death. Being a quaternary amine, Muscarine is less completely absorbed from the gastrointestinal tract than tertiary amines, but it does cross the blood brain barrier.^[1]

Muscarine mimics the action of the neurotransmitter acetylcholine at muscarinic acetylcholine receptors.

Muscarine poisoning is characterized by increased salivation, sweating (perspiration), and tearflow (lacrimation) within 15 to 30 minutes after ingestion of the mushroom. With large doses, these symptoms may be followed by abdominal pain, severe nausea, diarrhea, blurred vision, and labored breathing. Intoxication generally subsides within 2 hours. Death is rare, but may result from cardiac or respiratory failure in severe cases. The specific antidote is atropine.

Muscarine is only a trace compound in the fly agaric Amanita muscaria; the pharmacologically more relevant compound from this mushroom is muscimol.

Mushrooms in the genera Entoloma and Mycena have also been found to contain levels of muscarine which can be dangerous if ingested. Muscarine has been found in harmless trace amounts in Boletus, Hygrocybe, Lactarius and Russula.

External links

• Treatment of muscarine poisoning
• Psychoactive Amanitas on Erowid

References

• Katzung, Bertam G. (2004). Basic & Clinical Pharmacology (9th ed.). New York: Lange Medical Books. ISBN 0071410929. OCLC 54106245.