Unifiram

Base Information

• Chemical Name: Unifiram
• CAS No.: 272786-64-8
• Molecular Formula: C13H15FN2O3S
• Molecular Weight: 298.33300
• UNII: N4024LN29G
• DSSTox Substance ID: DTXSID00432024
• Nikkaji Number: J1.333.634B
• Wikipedia: Unifiram
• Wikidata: Q6590512
• ChEMBL ID: CHEMBL140717
• Mol file: 272786-64-8.mol

Synonyms:DM 232;DM-232;unifiram

Chemical Property of Unifiram

Chemical Property:

• Boiling Point: 479.5±55.0 °C(Predicted)
• PKA: -0.82±0.20(Predicted)
• PSA: 66.07000
• Density: 1.47±0.1 g/cm3(Predicted)
• LogP: 1.77760
• Storage Temp.: 2-8°C
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 298.07874168
• Heavy Atom Count: 20
• Complexity: 482

Purity/Quality:

99%, ^*data from raw suppliers

UNIFIRAM 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)N2C1CN(CC2)S(=O)(=O)C3=CC=C(C=C3)F
• Description: Unifiram (DM-232) is structurally similar to Sunifiram, and is a highly potent AMPAkine-line compound with effective cognition-enhancing and anti-amnesiac effects in animal models. Although sometimes grouped with racetam compounds, Unifiram is technically not a racetam due to the broken pyrrolidone backbone.Animal research has shown that Unifiram has a significantly greater Nootropic potency than Piracetam or Phenylpiracetam. Unifiram is shares structural similarities to Sunifiram. Animal models show similar modes of action for both compounds – increased cognitive performance and anti-amnesiac effects through interactions with the glutamatergic system and particularly through AMPA-receptor activation.
• Uses: Unifiram is a highly potent AMPAkine-like nootropic with antiamnesic and cognition-enhancing effects in animal studies at up to three orders of magnitude higher potency than piracetam.

Technology Process of Unifiram

There total 3 articles about Unifiram 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:

1,4-dibenzyl-2-piperazinecarboxaldehyde (54969-29-8) → Unifiram (272786-64-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaH / 1,2-dimethoxy-ethane / 1 h

1.2: 60 percent / 1,2-dimethoxy-ethane / 1 h / 20 °C

2.1: 72 percent / H₂ / Pd/C / ethanol / 8 h / 2585.81 Torr

3.1: Et₃N / acetonitrile / 2 h / 20 °C

With hydrogen; sodium hydride; triethylamine; palladium on activated charcoal; In 1,2-dimethoxyethane; ethanol; acetonitrile; 1.1: Metallation / 1.2: Substitution / 2.1: Catalytic hydrogenation / 3.1: sulfonylation;

DOI:10.1021/jm991170t

Reference yield:

methyl 1,4-dibenzyl-2-piperazin-3-acrylate → Unifiram (272786-64-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / H₂ / Pd/C / ethanol / 8 h / 2585.81 Torr

2: Et₃N / acetonitrile / 2 h / 20 °C

With hydrogen; triethylamine; palladium on activated charcoal; In ethanol; acetonitrile; 1: Catalytic hydrogenation / 2: sulfonylation;

DOI:10.1021/jm991170t

Reference yield:

4-Fluorobenzenesulfonyl chloride (349-88-2) + 2,3,4,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazin-6-one (117810-52-3) → Unifiram (272786-64-8)

Guidance literature:

With triethylamine; In acetonitrile; at 20 ℃; for 2h;

DOI:10.1021/jm991170t

upstream raw materials:

4-Fluorobenzenesulfonyl chloride

2,3,4,7,8,8a-hexahydro-1H-pyrrolo[1,2-a]pyrazin-6-one

1,4-dibenzyl-2-piperazinecarboxaldehyde

Refernces