(+)-Muscarine Iodide

Base Information

• Chemical Name: (+)-Muscarine Iodide
• CAS No.: 2209-02-1
• Molecular Formula: C9H20INO2
• Molecular Weight: 301.168
• European Community (EC) Number: 692-679-0
• DSSTox Substance ID: DTXSID90944722
• ChEMBL ID: CHEMBL292911
• Mol file: 2209-02-1.mol

Synonyms:(+)-Muscarine Iodide;24570-49-8;DL-Muscarine iodide;Muscarine (iodide);2209-02-1;[(2S,4R,5S)-4-hydroxy-5-methyloxolan-2-yl]methyl-trimethylazanium;iodide;2-Furanmethanaminium, tetrahydro-4-hydroxy-N,N,N,5-tetramethyl-, iodide, (2S-(2alpha,4beta,5alpha))-;Muscarine, iodide;(+-)-Muscarine iodide;CHEMBL292911;Muscarine (alkaloid), iodide, (+-)-;2,5-anhydro-1,4,6-trideoxy-6-(trimethylammonio)-d-ribo-hexitol iodide;(+)-Muscarine iodide;L-(+)-Muscarine iodide;L-Muscarine iodide;DTXSID90944722;2,5-Anhydro-1,4,6-trideoxy-6-(trimethylammonio)-D-ribohexitol Iodide;AKOS024457412;HY-107654;CS-0029057;2,5-Anhydro-1,3,6-trideoxy-1-(trimethylazaniumyl)hexitol iodide;1-((2S,4R,5S)-4-Hydroxy-5-methyltetrahydrofuran-2-yl)-N,N,N-trimethylmethanaminium iodide

Chemical Property of (+)-Muscarine Iodide

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: g/cm³
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 301.05388
• Heavy Atom Count: 13
• Complexity: 153

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(CC(O1)C[N+](C)(C)C)O.[I-]
• Isomeric SMILES: C[C@H]1[C@@H](C[C@H](O1)C[N+](C)(C)C)O.[I-]

Technology Process of (+)-Muscarine Iodide

There total 22 articles about (+)-Muscarine Iodide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 60.0%

(2S,3R,5S)-5-Iodomethyl-2-methyl-tetrahydro-furan-3-ol (85316-65-0) + trimethylamine (75-50-3) → (+/-)-muscarine iodide (2209-02-1)

Guidance literature:

In ethanol; at 80 ℃; for 6h; in autoclave;

DOI:10.1016/S0040-4039(00)85595-1

Reference yield:

(3R,5S,6S)-3,5-Bis-benzyloxymethoxy-6-methyl-tetrahydro-pyran-2-ol (74282-54-5) → (+/-)-muscarine iodide (2209-02-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 90 percent / CrO₃*2C₅H₅N / CH₂Cl₂

2: 97 percent / benzene / 3 h / 25 °C

3: 93 percent / Et₃N / CH₂Cl₂

4: 81 percent / H₂ / 10percent Pd/C / various solvent(s)

5: LiAlH₄ / diethyl ether / 1 h / Heating

With lithium aluminium tetrahydride; hydrogen; dipyridine chromium trioxide; triethylamine; palladium on activated charcoal; In diethyl ether; dichloromethane; benzene;

DOI:10.1021/jo01304a056

Reference yield:

(3S,5R,6R)-3,5-Bis-benzyloxymethoxy-6-methyl-tetrahydro-pyran-2-one (74282-55-6,74298-00-3) → (+/-)-muscarine iodide (2209-02-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 97 percent / benzene / 3 h / 25 °C

2: 93 percent / Et₃N / CH₂Cl₂

3: 81 percent / H₂ / 10percent Pd/C / various solvent(s)

4: LiAlH₄ / diethyl ether / 1 h / Heating

With lithium aluminium tetrahydride; hydrogen; triethylamine; palladium on activated charcoal; In diethyl ether; dichloromethane; benzene;

DOI:10.1021/jo01304a056

upstream raw materials:

(+/-)-normuscarine

(2S,3R,5S)-5-Iodomethyl-2-methyl-tetrahydro-furan-3-ol

dimethyl amine

methyl iodide

Downstream raw materials:

(+/-)-Muscarine chloride

[(2R)-(4c-hydroxy-5t-methyl-(2rH)-tetrahydro-furfuryl)-trimethyl-ammonium; di-O-p-toluoyl-D_g-hydrogentartrate