10-Methoxy-1,6-dimethylergoline-8beta-methanol

Base Information

• Chemical Name: 10-Methoxy-1,6-dimethylergoline-8beta-methanol
• CAS No.: 35155-28-3
• Molecular Formula: C18H24 N2 O2
• Molecular Weight: 300.401
• European Community (EC) Number: 252-405-9
• DSSTox Substance ID: DTXSID30956602
• Nikkaji Number: J127.326D
• Mol file: 35155-28-3.mol

Synonyms:1-methyl-10-methoxy-9,10-dihydrolysergol;1-methyl-10alpha-methoxy-9,10-dihydrolysergol;1-MMDL

Chemical Property of 10-Methoxy-1,6-dimethylergoline-8beta-methanol

Chemical Property:

• Vapor Pressure: 0Pa at 20℃
• Boiling Point: 459.8°Cat760mmHg
• PKA: 14.86±0.10(Predicted)
• Flash Point: 231.9°C
• PSA: 37.63000
• Density: 1.27g/cm³
• LogP: 1.82660
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: 446mg/L at 20℃
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 300.183778013
• Heavy Atom Count: 22
• Complexity: 431

Purity/Quality:

99.9% ^*data from raw suppliers

10α-Methoxy-1-methyl-9,10-dihydrolysergol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CN1CC(CC2(C1CC3=CN(C4=CC=CC2=C34)C)OC)CO
• Isomeric SMILES: CN1C[C@@H](C[C@]2([C@H]1CC3=CN(C4=CC=CC2=C34)C)OC)CO
• Uses: 10α-Methoxy-1-methyl-9,10-dihydrolysergol is a nicergoline (N394550) metabolite that has been shown to have antioxidant activity, preventing glutathione (GSH) depletion and lipid peroxidation; thus it has shown potential as treatment of neuroleptic-induced side effects.

Technology Process of 10-Methoxy-1,6-dimethylergoline-8beta-methanol

There total 9 articles about 10-Methoxy-1,6-dimethylergoline-8beta-methanol 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: 91.0%

nicergoline (27848-84-6,28057-46-7,58001-19-7,58001-20-0,58001-21-1,140387-88-8) → 5-bromo-3-pyridinecarboxylic acid (20826-04-4) + 1-Methyl-10alpha-methoxy-9,10-dihydrolysergol (35155-28-3)

Guidance literature:

With potassium hydroxide; In methanol; Heating;

DOI:10.1002/jps.2600840916

Reference yield: 68.9%

trimethylsulfoxonium iodide (1774-47-6) + 10alpha-methoxy-9,10-dihydrolysergol (35121-60-9) → 1-Methyl-10alpha-methoxy-9,10-dihydrolysergol (35155-28-3)

Guidance literature:

With potassium hydroxide; In dimethyl sulfoxide; at 10 - 40 ℃; for 1.5h;

Reference yield:

10alpha-methoxy-9,10-dihydrolysergol (35121-60-9) + methyl iodide (74-88-4) → 1-Methyl-10alpha-methoxy-9,10-dihydrolysergol (35155-28-3)

Guidance literature:

10alpha-methoxy-9,10-dihydrolysergol; With potassium hydroxide; In N,N-dimethyl acetamide; at 20 ℃; for 1h;

methyl iodide; In N,N-dimethyl acetamide; at 10 - 15 ℃; for 3h; Temperature; Solvent; Reagent/catalyst;

upstream raw materials:

nicergoline

lysergol

trimethylsulfoxonium iodide

10alpha-methoxy-9,10-dihydrolysergol

Downstream raw materials:

nicergoline

Refernces

• 1、 -. "Improved preparation method of nicergoline (by machine translation)". . . Retrieved 2020/05/30.
• 2、 -. "Synthetic method of nicergoline". . . Retrieved 2020/05/30.