(2S,4R,5S)-Muscarine

Base Information

• Chemical Name: (2S,4R,5S)-Muscarine
• CAS No.: 300-54-9
• Molecular Formula: C9H20 N O2
• Molecular Weight: 174.30
• DSSTox Substance ID: DTXSID101018055
• Nikkaji Number: J1.552.969E
• ChEMBL ID: CHEMBL404094
• Mol file: 300-54-9.mol

Synonyms:(2S,4R,5S)-Muscarine;(4-hydroxy-5-methyloxolan-2-yl)methyl-trimethylazanium;Muscarine II;CHEMBL404094;SCHEMBL17428402;DTXSID101018055;2,5-Anhydro-1,3,6-trideoxy-1-(trimethylazaniumyl)hexitol;Trimethyl(tetrahydro-4-hydroxy-5-methylfurfuryl)-Ammonium;Tetrahydro-4-hydroxy-N,N,N,5-tetramethyl-2-furanmethanaminium;7619-12-7

Chemical Property of (2S,4R,5S)-Muscarine

Chemical Property:

• Refractive Index: 1.4090 (estimate)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 29.46000
• Density: g/cm³
• LogP: 0.23090
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 174.149403881
• Heavy Atom Count: 12
• Complexity: 153

Purity/Quality:

99% ^*data from raw suppliers

MUSCARINE 95.00% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(CC(O1)C[N+](C)(C)C)O
• Uses: Cosmetics and perfumery (fixative), fragrances,mothproofing agent.

Refernces

3-Hydroxymuscarines from L-rhamnose

10.1016/S0040-4020(01)90162-0

The research focuses on the synthesis of muscarine analogues, specifically the epimeric 3-hydroxymuscarines (5 and 9), from L-rhamnose. The purpose of this study is to explore the potential of these analogues in providing insights into selective interactions with muscarinic receptors, which could lead to the development of chemotherapeutically useful compounds as specific muscarinic agonists or antagonists. The key chemicals involved include L-rhamnose as the starting material, various reagents such as triflic anhydride, lithium aluminum hydride, and tosyl chloride, and protecting groups like tert-butyldiphenylsilyl chloride. The synthesis involves multiple steps, including oxidation, esterification, reduction, and selective protection and deprotection of hydroxyl groups. The study concludes that L-rhamnose is a valuable precursor for the synthesis of muscarine and its analogues, and the tetrahydrofuran intermediate (7) is highly divergent for the synthesis of muscarine derivatives with functional groups at the C-3 position. The biological properties of these hydroxymuscarines and other analogues will be reported elsewhere.