Eutropoflavin
[CAS# 1205548-00-0]

Identification

• Classification: Natural product >> Flavonoids
• Name: Eutropoflavin
• Synonyms: 2-[4-(dimethylamino)phenyl]-7,8-dihydroxychromen-4-one
• Molecular Formula: C₁₇H₁₅NO₄
• Molecular Weight: 297.31
• CAS Registry Number: 1205548-00-0
• SMILES: CN(C)C1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C(=C(C=C3)O)O

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.695, Calc.^*
• Boiling Point: 535.1±50.0 ºC (760 mmHg), Calc.^*
• Flash Point: 277.4±30.1 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Discovory and Applicatios

Eutropoflavin, also known as 7,8-dihydroxyflavone (C15H10O4), is a synthetic flavonoid derivative that has garnered significant interest due to its unique neuroprotective properties. Structurally related to natural flavonoids, eutropoflavin is a potent and selective agonist of the TrkB (tropomyosin receptor kinase B) receptor, which is critical in mediating the effects of brain-derived neurotrophic factor (BDNF). This interaction underpins eutropoflavin's potential in treating a range of neurological disorders.

The discovery of eutropoflavin arose from efforts to identify small-molecule mimics of BDNF. BDNF plays a central role in neural survival, plasticity, and growth, but its therapeutic application is limited due to poor pharmacokinetic properties and challenges in crossing the blood-brain barrier. Researchers synthesized eutropoflavin to address these issues, resulting in a compound that effectively activates TrkB receptors, mimicking BDNF’s beneficial effects while offering better stability and bioavailability.

Eutropoflavin's neuroprotective properties have been extensively studied in preclinical models. It has demonstrated efficacy in preventing neuronal death and promoting synaptic plasticity, which are critical processes for learning and memory. These properties make it a promising candidate for treating neurodegenerative diseases such as Alzheimer's, Parkinson's, and Huntington's diseases. In animal models of Alzheimer's disease, eutropoflavin has been shown to reduce amyloid-beta plaque formation, improve cognitive function, and mitigate synaptic loss. Similarly, in Parkinson's disease models, the compound has protected dopaminergic neurons and alleviated motor dysfunction.

Beyond neurodegeneration, eutropoflavin has potential applications in treating psychiatric disorders. Preclinical studies suggest its efficacy in alleviating symptoms of depression and anxiety by modulating neuroplasticity and enhancing BDNF signaling. Its rapid onset of action compared to traditional antidepressants offers an additional advantage, making it a subject of interest for further clinical research.

Eutropoflavin's ability to facilitate neural regeneration has also been explored in the context of traumatic brain injury and spinal cord injury. By activating TrkB receptors, it promotes axonal outgrowth, reduces neuroinflammation, and improves functional recovery in animal models. These findings highlight its potential as a therapeutic agent for central nervous system injuries.

In addition to its neuroprotective effects, eutropoflavin has shown promise in peripheral applications. Research indicates that it may aid in cardiac and metabolic health by enhancing BDNF signaling in non-neuronal tissues. For instance, studies suggest a potential role in mitigating diabetic complications and improving cardiac function in heart failure.

Despite its promising preclinical results, the translation of eutropoflavin into clinical use faces challenges. Its pharmacokinetics, long-term safety, and efficacy in humans require comprehensive evaluation through clinical trials. However, its specific mechanism of action and diverse therapeutic potential continue to drive interest in its development.

Eutropoflavin represents a significant advance in neurotherapeutics, offering a novel approach to addressing unmet medical needs in neurological and psychiatric disorders. Its role as a TrkB agonist bridges a critical gap in translating the benefits of neurotrophic factors into viable therapies, making it a focal point for future research in neuroscience and beyond.