5-(p-Tolyl)-4,5-dihydrooxazol-2-amine
[CAS# 959249-62-8]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Amine
• Name: 5-(p-Tolyl)-4,5-dihydrooxazol-2-amine
• Molecular Formula: C₁₀H₁₂N₂O
• Molecular Weight: 176.22
• CAS Registry Number: 959249-62-8
• SMILES: CC1=CC=C(C=C1)C2CN=C(O2)N

Properties

• Solubility: 2059 mg/L (25 ºC water)
• Density: 1.2±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.609, Calc.^*
• Melting point: 87.76 ºC
• Boiling Point: 295.86 ºC, 310.4±52.0 ºC (760 mmHg), Calc.^*
• Flash Point: 141.5±30.7 ºC, Calc.^*

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

Discovory and Applicatios

5-(p-Tolyl)-4,5-dihydrooxazol-2-amine, also known as Toloxatone, was discovered during the mid-20th century as part of research into novel antidepressant medications. The compound was synthesized and evaluated for its pharmacological properties, particularly its potential to modulate neurotransmitter levels in the brain. Toloxatone belongs to the class of reversible monoamine oxidase inhibitors (MAOIs), which work by inhibiting the enzyme monoamine oxidase, leading to increased levels of neurotransmitters such as serotonin, dopamine, and norepinephrine in the brain. Its discovery marked a significant advancement in the treatment of depression, offering an alternative to traditional tricyclic antidepressants and selective serotonin reuptake inhibitors (SSRIs).

Toloxatone is used in the treatment of depression, particularly in cases where other antidepressant medications have been ineffective or poorly tolerated. As a reversible MAOI, Toloxatone inhibits the breakdown of neurotransmitters such as serotonin, dopamine, and norepinephrine, leading to increased synaptic levels of these neurotransmitters. This mechanism of action helps to alleviate depressive symptoms and improve mood in patients with major depressive disorder.

Toloxatone is particularly effective in treating atypical depression, a subtype of depression characterized by mood reactivity, increased appetite, weight gain, hypersomnia, and a sense of heaviness in the limbs. Unlike traditional MAOIs, Toloxatone has a lower risk of causing hypertensive crises or interactions with tyramine-containing foods, making it safer and more tolerable for patients.

Toloxatone may also be used in the treatment of anxiety disorders, such as generalized anxiety disorder (GAD) and social anxiety disorder (SAD). By modulating neurotransmitter levels in the brain, Toloxatone helps to reduce symptoms of anxiety, including excessive worry, nervousness, and avoidance behaviors.

Toloxatone and other reversible MAOIs are valuable tools for pharmacological research into the neurobiology of depression and mood disorders. Studying their effects on neurotransmitter systems and neuronal function provides insights into the underlying mechanisms of depression and informs the development of new antidepressant medications with improved efficacy and tolerability.

Toloxatone may be prescribed as adjunctive therapy in combination with other antidepressant medications or mood stabilizers for treatment-resistant depression or bipolar disorder. Combining Toloxatone with other medications can enhance the overall antidepressant effect and improve treatment outcomes in patients with complex mood disorders.

Despite the availability of newer antidepressant medications, Toloxatone remains a valuable option in clinical practice for patients who do not respond to conventional treatments or who experience intolerable side effects with other medications. Its unique mechanism of action and tolerability profile make it a useful addition to the armamentarium of antidepressant therapies.