Basic information
- CAS
300-54-9- Standard SMILES
C[C@@H]1O[C@H](C[N+](C)(C)C)C[C@H]1O- InChIKey
UQOFGTXDASPNLL-XHNCKOQMSA-N- Molecular formula
- C9H20NO2+
- Average molar mass
- 174.26 g/mol
- Monoisotopic mass
- 174.14940388
Overview
Muscarine is a monosaccharide.
Names & identifiers
- Preferred name
- Muscarine
- IUPAC
- [(2S,4R,5S)-4-hydroxy-5-methyloxolan-2-yl]methyl-trimethylazanium
- English name
- (+/-)-MUSCARINE CHLORIDE
- Molecular formula
- C9H20NO2+
- Molecular weight
- 174.26
Names & synonyms
MUSCARINE300-54-9L-(+)-MuscarineMuscarinMuskarinMuscarine (alkaloid)Muscarine (the alkaloid)(+)-(2S,4R,5S)-Muscarine7T101UWZ5W2-Furanmethanaminium, tetrahydro-4-hydroxy-N,N,N,5-tetramethyl-, (2S-(2alpha,4beta,5alpha))-[(2S,4R,5S)-4-hydroxy-5-methyloxolan-2-yl]methyl-trimethylazanium{[(2S,4R,5S)-4-hydroxy-5-methyloxolan-2-yl]methyl}trimethylazanium
Show more names
dl-muscarine(+)-L-Muscarinemuscarine(thealkaloid)(+)-MUSCARINE CHLORIDE(+/-)-MUSCARINE CHLORIDEtrimethyl(tetrahydro-4-hydroxy-5-methylfurfuryl)-ammoniu[(2S)-4β-Hydroxy-5α-methyloxolane-2α-yl]methyltrimethylaminium
((2S,4R,5S)-4-hydroxy-5-methyloxolan-2-yl)methyl-trimethylazanium(((2S,4R,5S)-4-hydroxy-5-methyloxolan-2-yl)methyl)trimethylazanium((2S,4R,5S)-4-hydroxy-5-methyl-tetrahydrofuran-2-yl)methyl-trimethyl-ammonium[(2S,4R,5S)-4-hydroxy-5-methyl-tetrahydrofuran-2-yl]methyl-trimethyl-ammoniumRefChem:160182206-094-1(+)-MuscarineCHEMBL12587
Properties
Computed structural properties
- XLogP
- 0.1
- Topological polar surface area
- 29.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 2
- Heavy atoms
- 12
- Formal charge
- 1
- Complexity
- 153
Physicochemical properties
- Boiling point
- 305.25 °C · 305.25°C (rough estimate)
- Density
- 1.0117 · 1.0117 (rough estimate)
- refractive index
- 1.409 · 1.4090 (estimate)
- solubility
- Water (Easy)
- FDA UNII
- 7 T101UWZ5W · 7T101UWZ5W
- Hazard Codes
- Xn
- Risk Statements
- 22 · 22-36
- Safety Statements
- 26 · 26-36
- WGK Germany
- 3 · 3
- Toxicity
- 50 in · A toxic alkaloid of the mushroom Amanita muscaria and certain other fungi. Although useful as a pharmacological tool, muscarine has no clinical or pesticidal applications. The compound is a potent and selective mimic of acetylcholine at parasympathetic neuromuscular junctions and at central muscarinic acetylcholine receptors. Symptoms of poisoning are primarily those attributable to peripheral parasympathetic stimulation (i.e., miosis, vomiting, diarrhea, bradycardia, and cardiovascular collapse). The i.v. LD50 in mice is 0.23 mg/kg.
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
TreatmentThe specific antidote is atropine. (L1011)
Health EffectsIntoxication generally subsides within 2 hours. Death is rare, but may result from cardiac or respiratory failure in severe cases. (L1011)
Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity SummaryMuscarine is a competitive inhibitor. It mimics the action of the neurotransmitter acetylcholine at acetylcholine receptors. (L1011)
Signs and Symptoms
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. (L1011)
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Safety data
- wgk
- 3
- Toxicity
- A toxic alkaloid of the mushroom Amanita muscaria and certain other fungi. Although useful as a pharmacological tool, muscarine has no clinical or pesticidal applications. The compound is a potent and selective mimic of acetylcholine at parasympathetic neuromuscular junctions and at central muscarinic acetylcholine receptors. Symptoms of poisoning are primarily those attributable to peripheral parasympathetic stimulation (i.e., miosis, vomiting, diarrhea, bradycardia, and cardiovascular collapse). The i.v. LD50 in mice is 0.23 mg/kg.
- risk_code
- 22-36
- hazard_code
- Xn
- safety_code
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Drugs that mimic the effects of parasympathetic nervous system activity. Included here are drugs that directly stimulate muscarinic receptors and drugs that potentiate cholinergic activity, usually by slowing the breakdown of acetylcholine (CHOLINESTERASE INHIBITORS). Drugs that stimulate both sympathetic and parasympathetic postganglionic neurons (GANGLIONIC STIMULANTS) are not included here.
Drugs that bind to and activate muscarinic cholinergic receptors (RECEPTORS, MUSCARINIC). Muscarinic agonists are most commonly used when it is desirable to increase smooth muscle tone, especially in the GI tract, urinary bladder and the eye. They may also be used to reduce heart rate.
Uses & manufacturing
Uses
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. (L1011)
Applications
UsesCosmetics and perfumery (fixative), fragrances,mothproofing agent.
Suppliers7 total
上海安化生物技术有限公司021-61263375 18168859245
BOC Sciences1-631-485-4226; 16314854226 · [email protected]
青岛海智微元生物科技有限公司18317699790 18317699790 · [email protected]
上海陶术生物科技股份有限公司
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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