Slaframine

Base Information

• Chemical Name: Slaframine
• CAS No.: 20084-93-9
• Molecular Formula: C₁₀H₁₈N₂O₂
• Molecular Weight: 198.265
• UNII: 51H2386GWI
• DSSTox Substance ID: DTXSID50942108
• Nikkaji Number: J15.531D
• Wikipedia: Slaframine
• Wikidata: Q1277175
• Mol file: 20084-93-9.mol

Synonyms:(1S,6S,8aS)-1-acetoxy-6-aminooctahydroindolizine;slaframine;slaframine citrate salt (1:2)

Chemical Property of Slaframine

Chemical Property:

• Vapor Pressure: 0.00425mmHg at 25°C
• Boiling Point: 278.5°Cat760mmHg
• Flash Point: 122.2°C
• PSA: 55.56000
• Density: 1.15g/cm³
• LogP: 0.75170
• XLogP3: 0
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 198.136827821
• Heavy Atom Count: 14
• Complexity: 232

Purity/Quality:

97% ^*data from raw suppliers

(-)-Slaframine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1CCN2C1CCC(C2)N
• Isomeric SMILES: CC(=O)O[C@H]1CCN2[C@H]1CC[C@@H](C2)N
• General Description: Slaframine, also known by various synonyms such as (-)-slaframine and 1-Indolizinol derivatives, is a fungal metabolite produced by *Rhizoctonia leguminicola*. It is notable for causing excessive salivation (slobber syndrome) in ruminants when ingested via contaminated forage. Beyond its toxicological effects, slaframine has demonstrated pharmacological potential, particularly in addressing cholinergic dysfunctions and symptoms related to cystic fibrosis due to its ability to stimulate salivary and secretory responses.

Technology Process of Slaframine

There total 114 articles about Slaframine 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: 95.0%

(1S,6S,8aS)-6-(benzyloxycarbonylamino)octahydroindolizin-1-yl acetate (153379-66-9) → (-)-slaframine (20084-93-9,25357-19-1,30591-15-2,83602-26-0,114817-63-9,132486-20-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; acetic acid; at 20 ℃; for 1h;

DOI:10.1016/0040-4039(93)88117-2

Reference yield: 79.0%

(1S,6S,8aS)-1-acetoxy-6-<(tert-butoxycarbonyl)amino>-1,2,3,5,6,7,8,8a-octahydroindolizine (146955-18-2) → (1S,6S,8aS)-1-acetoxy-6-aminooctahydroindolizidine (20084-93-9)

Guidance literature:

With trimethylsilyl iodide; In chloroform-d1; at 20 ℃; for 0.166667h;

DOI:10.1055/s-2002-28505

Reference yield: 78.0%

(1S,6S,8aS)-octahydro-1-acetoxy-6-indolizine (132317-05-6) → (1S,6S,8aS)-1-acetoxy-6-aminooctahydroindolizidine (20084-93-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; at 23 ℃; for 4h; under 760 Torr;

DOI:10.1021/jo00006a002

upstream raw materials:

(1S,6R,8aS)-1-acetoxy-6-<(tert-butoxycarbonyl)amino>-1,2,3,5,6,7,8,8a-octahydroindolizine

(R)-2-Benzyloxycarbonylamino-1-(tert-butyldimethylsilyloxy)-3-phenylsulfonylpropane

(1S,6S,8aS)-6-(benzyloxycarbonylamino)octahydroindolizin-1-yl acetate

Methyl (2R,3S)-1-(tert-butoxycarbonyl)-3-hydroxypyrrolidine-2-carboxylate

Downstream raw materials:

(1S,6S,8aS)-6-(benzyloxycarbonylamino)octahydroindolizin-1-yl acetate

Refernces

Enantiopure N-Acyldihydropyridones as Synthetic Intermediates: Asymmetric Synthesis of (-)-Slaframine

10.1021/ol991083v

The research focuses on the asymmetric synthesis of (?)-slaframine and its N-acetyl derivative, employing an enantiopure dihydropyridone as a key chiral building block. Slaframine is a metabolite produced by the fungus Rhizoctonia leguminicola, which has been noted for inducing excessive salivation in ruminants upon consumption of contaminated forage. Beyond its role as a mycotoxin, slaframine has shown potential as a drug candidate for treating symptoms associated with cystic fibrosis and diseases arising from cholinergic dysfunctions.