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Encyclopedia > Muscarine
Muscarine
Systematic name (2S,4R,5S)-(4-hydroxy-5-methyl-
tetrahydrofuran-2-ylmethyl)-
trimethyl-ammonium
Other names L-(+)-muscarine, muscarin
Chemical formula C9H20NO2+
Molecular mass 174.26 g/mol
CAS number [300-54-9]
SMILES O[C@@H]1C[C@@H](C[N+](C)(C)C)O[C@H]1C
Disclaimer and references

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. Muscarine has no effects on the central nervous system because it does not cross the blood-brain barrier due to its positively charged (polar) nitrogen atom. Image File history File links No higher resolution available. ... Image File history File links Chemical structure of muscarine Selfmade by cacycle File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... This article or section does not cite any references or sources. ... The molecular mass (abbreviated Mr) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... It has been suggested that this article or section be merged into natural product. ... Mushroom(s) are the fleshy, spore-bearing fruiting bodies of fungi typically produced above ground on soil or on their food sources. ... Inocybe is a large, complex genus of mushrooms. ... Hundreds of species of mushrooms compose the genus Clitocybe. ... Binomial name Clitocybe dealbata (Sowerby) Gillet (1874) The ivory funnel (Clitocybe dealbata) is a small white funnel-shaped toadstool widely found in lawns, meadows and other grassy areas in Europe and North America. ... Binomial name (L.:Fr. ... A parasympathomimetic is a drug or poison that acts by stimulating or mimicking the parasympathetic nervous system (PNS). ... The peripheral nervous system or PNS, is part of the nervous system, and consists of the nerves and neurons that reside or extend outside the central nervous system (the brain and spinal cord) to serve the limbs and organs, for example. ... Autonomic nervous system innervation, showing the sympathetic and parasympathetic (craniosacral) systems, in red and blue, respectively The parasympathetic nervous system is one of three divisions of the autonomic nervous system. ... A diagram showing the CNS: 1. ... Freeze-fracture morphology of the blood-brain barrier of a rat The blood-brain barrier (abbreviated BBB) is a membranic structure that acts primarily to protect the brain from chemicals in the blood, while still allowing essential metabolic function. ... Electric charge is a fundamental conserved property of some subatomic particles, which determines their electromagnetic interaction. ... General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless gas Standard atomic weight 14. ...


Muscarine mimics the action of the neurotransmitter acetylcholine at metabotropic receptors that are also known under the name muscarinic acetylcholine receptors. Chemical structure of D-aspartic acid, a common amino acid neurotransmitter. ... The chemical compound acetylcholine, often abbreviated as ACh, was the first neurotransmitter to be identified. ... Metabotropic receptor is a transmembrane receptor, which starts some intracellular biochemical cascade after its activation by an agonistic ligand. ... Amanita muscaria from which muscarine was isolated Acetylcholine - natural agonist of muscarinic and nicotinic 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. Saliva is the watery and usually somewhat frothy substance produced in the mouths of humans and some animals. ... Sweating (also called perspiration or sometimes transpiration) is the loss of a watery fluid, consisting mainly of sodium chloride and urea in solution, that is secreted by the sweat glands in the skin of mammals. ... Tears trickling down the cheeks Lacrimation is the bodys process of producing tears, which are a liquid to clean and lubricate the eyes. ... The abdomen (from the Latin word meaning belly) is the part of the body between the pelvis and the thorax. ... For the Beck song, see Nausea (song). ... Types 5-7 on the Bristol Stool Chart are often associated with diarrhea Diarrhea (in American English) or diarrhoea (in British English) is a condition in which the sufferer has frequent watery, loose bowel movements (from the Greek word διάρροια; literally meaning through-flowing). Acute infectious diarrhea is a common cause... This article or section does not adequately cite its references or sources. ... Congestive heart failure (CHF) (also called heart failure) is the inability of the heart to pump blood effectively to the body, or requiring elevated filling pressures in order to pump effectively. ... Respiratory failure is a medical term for inadequate gas exchange by the respiratory system. ... An antidote is a substance which can counteract a form of poisoning. ... Atropine is a tropane alkaloid extracted from the deadly nightshade (Atropa belladonna) and other plants of the family Solanaceae. ...


Muscarine is only a trace compound in the fly agaric Amanita muscaria; the pharmacologically more relevant compound from this mushroom is muscimol. Binomial name (L.:Fr. ... Muscimol (agarin, pantherine) is the psychoactive compound present in Amanita muscaria and Amanita Pantherina. ...


Mushrooms in the genuses Entoloma and Mycena have also been to 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. Species Entoloma sinuatum Entoloma abortivum Entoloma (or pinkgills) is a genus of terrestrial pink-spored mushrooms. ... Type species Mycena galericulata Species See text Mycena is a large genus of small saprophytic mushrooms which are rarely more than a few centimeters in width. ... Members of the order Boletales (commonly referred to as Boletes) are mushrooms characterized by holding their spores in small pores on the underside of the mushroom, instead of gills (as are found in agarics). ... Genera Hygrophorus Hygrocybe Camarophyllus Camarophyllopsis The family Hygrophoraceae, also known as waxy caps or waxcaps, is a taxon of white-spore agarics. ... Species blennius deliciosus pyrogalus quietus tabidus torminosus vellerius vietus etc. ... Around 750 worldwide species of mushrooms compose the genus Russula. ...


External links

  • Treatment of muscarine poisoning
  • Psychoactive Amanitas on Erowid

References

  • Katzung, Bertam G. Basic and Clinical Pharmacology, 9th ed. (2004). ISBN 0-07-141092-9

  Results from FactBites:
 
Reference.com/Encyclopedia/Muscarine (279 words)
Muscarine has no effects on the central nervous system because it does not cross the blood-brain barrier due to its positively charged (polar) nitrogen ion.
Muscarine mimics the action of the neurotransmitter acetylcholine at metabotropic receptors that are also known under the name 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.
Muscarine - Definition, explanation (202 words)
Muscarine has no effects on the central nervous system because it does not cross the blood-brain barrier due to its positively charged nitrogen atom.
Muscarine mimics the action of the neurotransmitter acetylcholine at metabotropic acetylcholine receptors that are also known under the name 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.
  More results at FactBites »

 
 

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