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CAS 300-54-9

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Muscarine

Description:
Muscarine is a naturally occurring alkaloid primarily found in certain mushrooms, notably those of the genus Amanita, such as Amanita muscaria. It is a quaternary ammonium compound, characterized by its ability to mimic the action of the neurotransmitter acetylcholine at muscarinic acetylcholine receptors. Muscarine is known for its potent parasympathomimetic effects, which can lead to symptoms such as salivation, lacrimation, urination, diarrhea, gastrointestinal distress, and bradycardia when ingested. The compound is soluble in water and exhibits a positive charge at physiological pH, which influences its interaction with biological systems. Due to its toxicological profile, muscarine is considered a poison, and its effects can be severe, necessitating medical attention in cases of mushroom poisoning. Its chemical structure includes a bicyclic framework and a hydroxyl group, contributing to its biological activity. Understanding muscarine's properties is crucial for both toxicology and pharmacology, as it provides insights into cholinergic signaling pathways.
Formula:C9H20NO2
InChI:InChI=1S/C9H20NO2/c1-7-9(11)5-8(12-7)6-10(2,3)4/h7-9,11H,5-6H2,1-4H3/q+1/t7-,8-,9+/m0/s1
InChI key:InChIKey=UQOFGTXDASPNLL-XHNCKOQMSA-N
SMILES:C([N+](C)(C)C)[C@@H]1C[C@@H](O)[C@H](C)O1
Synonyms:
  • (+)-(2S,4R,5S)-Muscarine
  • (2S-(2alpha,4beta,5alpha))-(Tetrahydro-4-hydroxy-5-methylfurfuryl)trimethylammonium
  • 2,5-Anhydro-1,4,6-trideoxy-6-(trimethylammonio)-<span class="text-smallcaps">D</span>-ribo-hexitol
  • 2,5-anhydro-1,4,6-trideoxy-6-(trimethylammonio)-D-ribo-hexitol
  • 2-Furanmethanaminium, tetrahydro-4-hydroxy-N,N,N,5-tetramethyl-, (2S-(2alpha,4beta,5alpha))-
  • 2-Furanmethanaminium, tetrahydro-4-hydroxy-N,N,N,5-tetramethyl-, [2S-(2α,4β,5α)]-
  • <span class="text-smallcaps">D</span>-ribo-Hexitol, 2,5-anhydro-1,4,6-trideoxy-6-(trimethylammonio)-
  • <span class="text-smallcaps">L</span>-(+)-Muscarine
  • Ammonium, trimethyl(tetrahydro-4-hydroxy-5-methylfurfuryl)-
  • D-ribo-Hexitol, 2,5-anhydro-1,4,6-trideoxy-6-(trimethyl)ammonio)-
  • See more synonyms
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