Troparil(also named WIN 35065), is a central nervous system stimulant that belongs to the class of pharmaceutical compounds known for their stimulatory effects on the central nervous system. It is a chemical compound with the molecular formula C16H21NO2 CAS 74163-84-1 and a molecular weight of 259.34.
It is characterized by its specific chemical structure, which includes a 2-beta-methoxycarbonyl-3-beta-phenyltropane moiety. This structure gives the compound its unique pharmacological properties. It's synonyms include 2-BETA-Methoxycarbonyl-3-BETA-Phenyltropane, among others, reflecting its various chemical descriptions.
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Physical Properties
Color and Appearance: Generally a white to off-white crystalline solid. Its purity and processing conditions may influence the exact hue, but it remains visually distinguishable as a solid compound.
Density: Has a density of approximately 1.09 grams per cubic centimeter. This density allows it to be easily measured and handled in various industrial and laboratory settings.
Melting Point and Boiling Point: While the exact melting point is not commonly cited, its predicted boiling point is 350.2°C ± 42.0°C. This high boiling point indicates that it is relatively stable under normal conditions and requires significant heat to vaporize.
Chemical Properties
Structural Characteristics: Belongs to a class of compounds known as tropane derivatives. Its structure features a tropane ring system with specific substituents that contribute to its unique pharmacological properties.
Solubility: The solubility in various solvents is not widely reported. However, its chemical properties suggest that it may be soluble in organic solvents such as ethanol or ether.
| Chemical Formula | C16H21NO2 |
| Exact Mass | 259.16 |
| Molecular Weight | 259.35 |
| m/z | 259.16 (100.0%), 260.16 (17.3%), 261.16 (1.4%) |
| Elemental Analysis | C, 74.10; H, 8.16; N, 5.40; O, 12.34 |
| Boiling Point | 350.2±42.0 °C(Predicted) |
| Density | 1.099±0.06 g/cm3(Predicted) |
| Acidity Coefficient (pKa) | 9.95±0.60(Predicted) |
Synthesis Method
The synthesis often begins with the preparation of the necessary starting materials. These may include tropane derivatives, appropriate alkylating agents, and other reagents required for the subsequent reactions.
A key step in the synthesis is the alkylation of a tropane derivative, such as tropine, with an appropriate alkylating agent. This reaction introduces the desired alkyl group into the tropane ring system. The reaction conditions, such as solvent, temperature, and catalyst, are optimized to promote efficient alkylation.
After successful alkylation, the resulting product is further functionalized to introduce the desired substituents. This may involve reactions such as oxidation, reduction, substitution, or addition of functional groups. The specific reaction pathway and conditions are chosen based on the desired structure.
Once the desired structure is achieved, the product is purified and isolated from the reaction mixture. This may involve techniques such as extraction, crystallization, chromatography, or distillation. The purity of the isolated product is analyzed using spectroscopic methods such as NMR or HPLC to ensure it meets the desired specifications.
Finally, the synthesized Troparil is characterized using various analytical techniques. These may include determination of physical properties (e.g., melting point, boiling point), chemical analysis (e.g., elemental analysis, mass spectrometry), and spectroscopic methods (e.g., NMR, IR). The characterization data confirms the identity and purity.
It is important to note that the specific synthesis method may vary depending on the availability of starting materials, reaction conditions, and the desired purity and yield. The outlined steps serve as a general guideline for understanding the synthesis procedure and may require adaptation for specific applications.
Pharmaceutical Applications
Cardiovascular Diseases: Plays a significant role in the treatment of cardiovascular diseases, particularly hypertension. It works by inhibiting vasoconstriction, thereby reducing blood pressure and lessening the burden on the heart. This reduction in blood pressure can contribute to a decrease in the occurrence of cardiovascular events.
Neurological Diseases: In the field of neurology, it is used to treat diseases such as Parkinson's disease. This degenerative neurological condition is characterized by symptoms like tremor, muscle rigidity, and motor dysfunction. It can help alleviate these symptoms, improving the quality of life for patients.
Agricultural Applications
It also finds use in the agricultural sector as an insecticide. Its ability to effectively control the reproduction and spread of pests makes it a valuable tool in ensuring crop health and yield. With the increasing global demand for food and concern for food security, it's role in agriculture is expected to grow.
Pharmaceutical Manufacturing
In the pharmaceutical industry, it serves as a carrier, solvent, and stabilizer. Its incorporation into drug formulations enhances the stability and bioavailability of medications, ensuring their efficacy and safety. As the demand for medications continues to rise due to factors like population aging and the increasing prevalence of chronic diseases, it's role in pharmaceutical manufacturing becomes increasingly crucial.
Detailed Mechanism in Treating Neurological Diseases
In the realm of neurological diseases, Troparil has exhibited promising therapeutic effects, particularly in the treatment of Parkinson's disease. Here, we delve deeper into the mechanism in addressing this degenerative neurological condition.
Parkinson's disease is characterized by the progressive loss of dopaminergic neurons in the substantia nigra of the midbrain, leading to a decrease in the neurotransmitter dopamine in the striatum. This imbalance in neurotransmission results in the cardinal motor symptoms of the disease: tremor, rigidity, bradykinesia, and postural instability.
It's therapeutic effects in Parkinson's disease stem from its ability to modulate neurotransmission in the affected brain regions. Specifically, it works by enhancing dopaminergic transmission, either directly or indirectly. This modulation helps restore the balance of neurotransmitters in the striatum, thereby alleviating the motor symptoms of the disease.
Some studies suggest that it may bind to specific receptors in the brain, such as dopamine receptors, and act as a partial agonist or antagonist. This binding alters the signaling pathways within neurons, leading to changes in neurotransmitter release and postsynaptic responses. These changes, in turn, influence motor function and help mitigate the symptoms of Parkinson's disease.
Moreover, it may also have neuroprotective effects, helping to preserve and even regenerate dopaminergic neurons in the substantia nigra. This neuroprotective action may contribute to the long-term benefits of it in the treatment of Parkinson's disease.
In summary, it's therapeutic effects in neurological diseases, especially Parkinson's disease, stem from its ability to modulate neurotransmission and enhance dopaminergic transmission. Its neuroprotective properties further add to its efficacy in treating this degenerative condition. However, further research is needed to fully understand the precise mechanism of action of Troparil in the brain.
Contrast
Troparil (2-methoxycarbonyl-3-phenyltropane) has the following potential advantages compared to cocaine:
Higher activity and lower toxicity
According to a 1985 study, it was proven to be an efficient neural activity stimulant, with higher efficacy than amphetamines but lower toxicity
Safer range of use
Due to its low toxicity, it may provide a safer treatment window, reducing the risk of cardiac toxicity and central nervous system suppression associated with high-dose cocaine use.
Longer duration of action
Due to the lack of metabolically unstable ester bonds between phenyl and alkane rings, its duration of action is much longer than cocaine, which means that less dosage may be required to maintain its effect.
No local anesthetic effect
Unlike cocaine, it does not have a local anesthetic effect, which eliminates the potential side effects such as corneal opacity that cocaine may cause as a local anesthetic.
Reduce cardiac toxicity
Due to its lower cardiac toxicity compared to cocaine, it may become a safer option in situations where stimulant effects are needed rather than anesthetic effects.
Reduce addiction
It may have lower psychological dependence and addiction than cocaine, although more research is needed to confirm this.
What are the side effects of this compound?
- The types and severity of side effects: Doctors will monitor the possible side effects it may cause, including but not limited to cardiovascular, neurological, and psychological effects. As it is a central nervous system stimulant, doctors may pay special attention to its effects on heart rate, blood pressure, and mental health.
- Dose dependence: The occurrence of side effects may be dose-dependent. Doctors will evaluate the incidence and severity of side effects at different doses to determine the optimal treatment dose.
- Individual differences: Different patients may have different reactions to it. Doctors will consider the patient's age, gender, weight, health status, and genetic factors, which may all affect the presentation of side effects.
- The effects of long-term use: Long term use may lead to increased tolerance or development of dependence. Doctors will monitor patients for a trend of increasing dosage and the appearance of withdrawal symptoms.
- Drug interactions: Doctors will evaluate its potential interactions with other drugs as this may increase the risk of side effects.
- Clinical monitoring and laboratory testing: Doctors may regularly conduct blood tests and other laboratory tests to monitor its potential side effects.
- Patient reporting and self-assessment: Doctors will encourage patients to report any discomfort or side effects, which can help identify and address issues in a timely manner.
- Risk and benefit assessment: Doctors will comprehensively consider its treatment effectiveness and side effects, and provide personalized treatment recommendations for patients
Frequently Asked Questions
What is Troparil used for?
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Troparil is an oxytocin receptor analog that can be used to diagnose the presence of this receptor in the human brain. It has a psychostimulant effect, and has been used for treating hyperactivity and other disorders.
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