Muscarine

Title: Muscarine
CAS Registry Number: 300-54-9
CAS Name: [2S-(2a,4b,5a)]-Tetrahydro-4-hydroxy-N,N,N,5-tetramethyl-2-furanmethanaminium
Molecular Formula: [C9H20NO2]+
Literature References: Alkaloid from the red variety of Amanita muscaria (L.) Pers., Agaricaceae, the fly fungus, a poisonous mushroom. Also found in some other fungi: Inocybe patouillardi; I. fastigiata, I. umbrina; I. rimosa. Isoln procedure for the naturally occurring L-(+)-form: Kuehl et al., J. Am. Chem. Soc. 77, 6663 (1955); Eugster, Helv. Chim. Acta 39, 1002 (1956). Structure and synthesis of racemate: Kögl et al., Rec. Trav. Chim. 76, 109 (1957); Kögl et al., Experientia 13, 137, 138 (1957); Cox et al., Helv. Chim. Acta 41, 229 (1958). Alternate syntheses: GB 828395 (1960 to Hoffmann-La Roche); Matsumoto et al., Tetrahedron 25, 5889 (1969); W. C. Still, J. A. Schneider, J. Org. Chem. 45, 3375 (1980). Synthesis of muscarine: Whiting et al., Can. J. Chem. 50, 3322 (1972); A. M. Mubarak, D. M. Brown, Tetrahedron Lett. 21, 2453 (1980); eidem, J. Chem. Soc. Perkin Trans. 1 1982, 809; S. Pochet, T. Huynhdinh, J. Org. Chem. 47, 193 (1982). Chemistry and pharmacology: Waser, Pharmacol. Rev. 13, 465-515 (1961). Toxicity study: P. J. Fraser, Br. J. Pharmacol. 12, 47 (1957). Reviews: C. H. Eugster, Adv. Org. Chem. 2, 427-455 (1960); S. Wilkinson, Q. Rev. Chem. Soc. 15, 153-171 (1961). Configurational relationship in the muscarine series: Bollinger, Eugster, Helv. Chim. Acta 54, 2704 (1971).
Derivative Type: Chloride
Molecular Formula: C9H20ClNO2
Molecular Weight: 209.71
Percent Composition: C 51.55%, H 9.61%, Cl 16.91%, N 6.68%, O 15.26%
Properties: Stout prisms from ethanol + acetone, mp 180-181°. Extremely hygroscopic. [a]D25 +8.1° (c = 3.5 in ethanol). Very sol in water, ethanol. Slightly sol in chloroform, ether, acetone. Aq solns are stable. LD50 i.v. in mice: 0.23 mg/kg (Fraser).
Melting point: mp 180-181°
Optical Rotation: [a]D25 +8.1° (c = 3.5 in ethanol)
Toxicity data: LD50 i.v. in mice: 0.23 mg/kg (Fraser)
CAUTION: Potential symptoms of toxicity following ingestion are profuse sweating, increased salivation, visual disturbances, nausea, vomiting, abdominal colic, diarrhea, headache, and bronchospasm. Very high doses may produce lacrimation, incontinence, bradycardia, hypotension and shock. See Clinical Toxicology of Commercial Products, R. E. Gosselin et al., Eds. (Williams & Wilkins, Baltimore, 5th ed., 1984) Section II, p 247.
Therap-Cat: Cholinergic.
Keywords: Cholinergic.
Muscazone Muscimol Muscone Musks Mustard

Muscarine
Chemical structure of muscarine
Muscarine-3D-balls.png
Identifiers
CAS number 300-54-9 YesY
PubChem 9308
ChemSpider 8949 YesY
ChEMBL CHEMBL12587 YesY
Jmol-3D images Image 1
Properties
Molecular formula C9H20NO2+
Molar mass 174.26 g/mol
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 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. 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. Muscarine is only a trace compound in the fly agaric Amanita muscaria; the pharmacologically more relevant compound from this mushroom is muscimol. The A. muscaria contains a variable dose of muscarine, usually around 0.0003% fresh weight. This is very low and toxicity symptoms occur very rarely. Inocybe and Clitocybe contain muscarine concentrations up to 1.6%.[1]

It is a nonselective agonist of the muscarinic acetylcholine receptor.