Structure via PubChem · Public domain (PubChem)
Chemical data
- Formula
- C9H20NO2+
- Molecular weight
- 174.26 g/mol
- IUPAC name
- [(2S,4R,5S)-4-hydroxy-5-methyloxolan-2-yl]methyl-trimethylazanium
- SMILES
- C[C@H]1[C@@H](C[C@H](O1)C[N+](C)(C)C)O
- InChIKey
- UQOFGTXDASPNLL-XHNCKOQMSA-N
- XLogP
- 0.1
- Polar surface area
- 29.5 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 1
via PubChem
Research
283,410 papers- The Bronchodilator and Anti-Inflammatory Effect of Long-Acting Muscarinic Antagonists in Asthma: An EAACI Position Paper.Allergy · 2025
- The Fatal Mushroom Neurotoxin Muscarine is Released from a Harmless Phosphorylated Precursor upon Cellular Injury.Angewandte Chemie (International ed. in English) · 2024
- Design, synthesis and preclinical evaluation of muscarine receptor antagonists via a scaffold-hopping approach.European journal of medicinal chemistry · 2023
- Endocannabinoids mediate muscarine-induced synaptic depression at the vertebrate neuromuscular junction.The European journal of neuroscience · 2007
- Muscarine enhances soluble amyloid precursor protein secretion in human neuroblastoma SH-SY5Y by a pathway dependent on protein kinase C(alpha), src-tyrosine kinase and extracellular signal-regulated kinase but not phospholipase C.Brain research. Molecular brain research · 2002
via PubMed
~9 min read
Encyclopedic overview
13 sectionsContents
- History
- Structure and reactivity
- Efficient synthesis of (+)-muscarine
- Other Syntheses
- Pharmacology
- Pharmacodynamics
- Metabolism
- Medical uses
- Efficacy
- Toxicology
- Antidote
- References
- External links
thumb|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 the genera Boletus, Hygrocybe, Lactarius and Russula. Trace concentrations of muscarine are also found in Amanita muscaria, though the pharmacologically more relevant compound from this mushroom is the gabaergic drug muscimol. A. muscaria fruitbodies contain a variable dose of muscarine, usually around 0.0003% of total fresh weight. This is very low and toxicity symptoms occur very rarely. Highly toxic Inocybe and Clitocybe species contain muscarine concentrations up to 1.6%.
Excerpted from Wikipedia’s “muscarine” article, available under the CC BY-SA 4.0 licence.