(+)-Muscarine Iodide

Base Information

• Chemical Name: (+)-Muscarine Iodide
• CAS No.: 24570-49-8
• Molecular Formula: C9H20 N O2 . I
• Molecular Weight: 301.168
• European Community (EC) Number: 692-679-0
• DSSTox Substance ID: DTXSID90944722
• ChEMBL ID: CHEMBL292911
• Mol file: 24570-49-8.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:

• PSA: 29.46000
• LogP: -2.76510
• 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:

98%Min ^*data from raw suppliers

(+)-MuscarineIodide ^*data from reagent 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-]
• Uses: A cholinergic receptor involved in the production of gastric acid

Technology Process of (+)-Muscarine Iodide

There total 62 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: 96.0%

(-)-(2S,4R,5S)-2-(Iodomethyl)-4-hydroxy-5-methyltetrahydrofuran (103664-41-1) + trimethylamine (75-50-3) → (+)-muscarine iodide (24570-49-8)

Guidance literature:

In ethanol; at 80 ℃; for 2h;

DOI:10.1002/jlac.198719870103

Reference yield:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) → (+)-muscarine iodide (24570-49-8)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 86 percent / Et₃N; DMAP / CH₂Cl₂ / 3 h / 0 - 20 °C

2.1: 95 percent / DIBAL / CH₂Cl₂ / 2 h / -78 °C

3.1: 77 percent / mesyl chloride; triethylamine / CH₂Cl₂ / 2.5 h / -20 - 40 °C

4.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 - 0 °C

4.2: 85 percent / TMEDA / tetrahydrofuran / 12 h / 20 °C

5.1: ThxBH₂ / tetrahydrofuran / 16 h / 0 °C

5.2: 59 percent / aq. NaOH; aq. H₂O₂ / 6 h / 20 °C

6.1: 93 percent / TBAF / tetrahydrofuran / 2 h / 0 - 20 °C

7.1: 74 percent / triphenylphosphine; iodine; imidazole / toluene / 3 h / 70 °C

8.1: 92 percent / ethanol / 3 h / Heating

With 1H-imidazole; dmap; tetrabutyl ammonium fluoride; iodine; tert.-butyl lithium; diisobutylaluminium hydride; methanesulfonyl chloride; triethylamine; triphenylphosphine; In tetrahydrofuran; ethanol; dichloromethane; toluene;

DOI:10.1016/j.tetlet.2007.03.014

Reference yield:

2,5-anhydro-3-O-methanesulfonyl-L-idose ethylene acetal (218449-02-6) → (+)-muscarine iodide (24570-49-8)

Guidance literature:

Multi-step reaction with 13 steps

1: 87 percent / toluene-4-sulfonic acid / 24 h / 20 °C

2: 76 percent / Bu₄NF / acetonitrile / 48 h / Heating

3: 94 percent / H₂ / PtO₂ / ethanol / 24 h / 20 °C

4: 79 percent / CF₃COOH / methanol / 0.5 h / 20 °C

5: 80 percent / pyridine / 144 h / -28 °C

6: 90 percent / LiAlH₄ / tetrahydrofuran / 4 h / Heating

7: 80 percent / pyridine / 48 h / 20 °C

8: 66 percent / dimethylformamide / 24 h / 100 °C

9: 0.7 g / trifluoroacetic acid; aq. HCl / 24 h / 4 °C

10: NaBH₄ / methanol / 2 h / 20 °C

11: 84 percent / imidazole; Ph₃P; iodine / toluene / 3 h / Heating

12: 83 percent / K₂CO₃ / methanol; tetrahydrofuran / 1.5 h / 20 °C

13: 93 percent / ethanol / 3 h / 80 °C

With pyridine; 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; hydrogen; iodine; potassium carbonate; toluene-4-sulfonic acid; triphenylphosphine; trifluoroacetic acid; platinum(IV) oxide; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide; toluene; acetonitrile; 1: cyclocondensation / 2: Elimination / 3: Catalytic hydrogenation / 4: Hydrolysis / 5: Tosylation / 6: Reduction / 7: Tosylation / 8: Substitution / 9: Oxidation / 10: Reduction / 11: Substitution / 12: Hydrolysis / 13: Addition;

DOI:10.1016/S0040-4020(00)00482-8

upstream raw materials:

(-)-(2S,4R,5S)-2-(Iodomethyl)-4-hydroxy-5-methyltetrahydrofuran

dimethyl amine

methyl iodide

(-)-normuscarine

Downstream raw materials:

(+)-muscarine chloride

L-(+)-muscarine tetraphenylborate