Nortropinone Hydrochloride CAS 25602-68-0

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Nortropinone Hydrochloride is an important derivative of tropane-type alkaloids, characterized by its unique bicyclic nitrogen heterocyclic framework. As the structural nucleus of key pharmacophores in natural products such as atropine and cocaine, it holds a foundational position in drug chemistry and neuropharmacology research. The hydrochloride form of this compound significantly enhances its water solubility and crystallization stability, greatly facilitating laboratory operations and potential drug development processes.

The chemical information of it is shown in the following table:

Its pharmacological mechanism mainly stems from precise intervention in the central and peripheral cholinergic nervous systems, and can effectively block muscarinic acetylcholine receptors as a competitive antagonist, thereby being used in research to explore physiological and pathological processes such as smooth muscle spasm, glandular secretion, and advanced brain functions. Currently, it is not only an indispensable tool molecule for elucidating the structure-activity relationship of tropane-type compounds, but also an important starting material and structural template for designing and synthesizing new antispasmodics, anti-Parkinson's disease drugs, and central nervous system active lead compounds, continuously driving the innovation process in neuroscience and related therapeutic fields.

Nortropinone Hydrochloride (CAS number: 25602-68-0) is a biochemical reagent with a unique chemical structure, with the molecular formula C ₇ H ₁ ClNO and a molecular weight of 161.63. This compound has demonstrated extensive application value in the fields of life sciences, drug development, and chemical research. The following is a detailed description of its uses:

It can serve as a modifying component of the extracellular matrix, simulating specific physiological or pathological environments by regulating cell adhesion, proliferation, and differentiation processes. For example, in neuronal culture, this compound can induce synaptic plasticity changes in neurons, providing a model for studying the pathogenesis of neurodegenerative diseases such as Alzheimer's disease. In addition, the nitrogen atoms and carbonyl functional groups in its structure can undergo non covalent interactions with biomolecules such as proteins and nucleic acids, which are used to study intermolecular recognition and binding mechanisms.

 

Developing novel bioactive molecules as organic synthesis intermediates

It is a key intermediate for the synthesis of various bioactive derivatives. By modifying its nitrogen atom or carbon skeleton, different functional groups can be introduced to obtain compounds with anti-tumor, anti-inflammatory, or antibacterial activities.For example, research and development of anti-tumor drugs: compounds with tubulin inhibitory activity can be synthesized by introducing fluorine atoms or aromatic rings with it as the skeleton.

Applications in Neuroscience Research:

The chemical structure of this drug shares similarities with certain neurotransmitters such as acetylcholine, making it suitable for studying neural signaling mechanisms. In neuronal electrophysiological experiments, this compound competitively binds to nicotinic acetylcholine receptors and reveals the receptor-mediated ion channel opening pattern by recording membrane potential changes. In addition, its derivatives can also serve as fluorescent probes for real-time monitoring of calcium ion concentration dynamics in living cells, providing technical support for studying neuronal excitability.

Research on antiepileptic drugs: By introducing sulfur atoms or cyclopropane groups, the inhibitory effect of compounds on voltage-gated sodium channels can be enhanced, thereby reducing neuronal hyperexcitability. Animal experiments have shown that such derivatives can significantly reduce the frequency of epileptic seizures without significant cognitive impairment.

Potential in multi-target drug development:

With a deeper understanding of the complexity of diseases, the development of multi-target drugs has become a current hot topic. This due to its multiple modifiable sites in its structure, can simultaneously act on multiple disease-related targets.

For example, anti-tumor combination therapy: By coupling This medicine with paclitaxel, a bifunctional compound that targets both microtubule protein and epidermal growth factor receptor (EGFR) can be synthesized. This type of compound has shown synergistic killing effect on non-small cell lung cancer cell line A549 in vitro experiments, and can overcome the problem of single drug resistance.

Metabolic syndrome treatment:-By introducing peroxisome proliferator activated receptor (PPAR) agonist structural fragments, compounds that simultaneously regulate glucose and lipid metabolism and have anti-inflammatory effects can be obtained. Animal experiments have shown that such derivatives can significantly improve insulin sensitivity in obese mice and reduce serum levels of inflammatory factors. 

Application in drug delivery systems:

Nortropinone Hydrochloride can also be used to construct targeted drug delivery systems. By combining it with polymer materials such as polylactic acid hydroxyacetic acid copolymer (PLGA), nanoparticle carriers can be formed to achieve precise drug delivery.

For example, brain targeted delivery: By utilizing Nortropine Hydrochloride's ability to penetrate the blood-brain barrier, it can be modified onto the surface of nanoparticles to achieve efficient delivery of anti Alzheimer's disease drugs (such as donepezil) in the brain. Animal experiments have shown that such delivery systems can increase the concentration of drugs in brain tissue by more than 5 times and significantly improve cognitive dysfunction. Tumor targeted therapy: By coupling Nortropinone Hydrolide with folate molecules, a targeted delivery system for tumors with high expression of folate receptors (such as breast cancer and ovarian cancer) can be constructed. This type of system can achieve specific accumulation of drugs in tumor tissues and reduce toxicity to normal tissues.

Participate in synthetic reactions as a chemical reagent&Standardized application in scientific experiments: 

It has significant value in organic synthesis. The nitrogen atoms and carbonyl functional groups in its structure can participate in various reactions, such as nucleophilic substitution reactions: reacting with alcohol compounds to form ether derivatives, which are commonly used in drug synthesis to construct chiral centers.

Addition reaction: Reacts with Grignard reagent to produce alcohol compounds, which play a crucial role in the total synthesis of natural products. Redox reaction: Under the action of a catalyst, it can be reduced to demethylpyrrolidone or oxidized to the corresponding carboxylic acid derivatives, providing various pathways for structural modification.This is often used as a standard compound or reference substance for calibrating experimental instruments, validating experimental methods, or serving as an experimental control.

For example, high-performance liquid chromatography (HPLC) analysis: used as a retention time reference to determine the peak position of the target compound in the sample. Mass spectrometry (MS) analysis: used as a molecular weight standard to verify the calibration accuracy of mass spectrometers. Cell viability assay: used as a positive or negative control to evaluate the biological activity of other compounds.

Demonstrative role in chemistry education: 

The unique structure and properties of it make it an ideal case for chemistry education.

By guiding students to participate in experimental activities such as synthesis, property research, or application exploration, it can stimulate their interest in organic chemistry and medicinal chemistry.

For example, structural modification experiment: Students are required to synthesize derivatives of this through esterification or amidation reactions, and compare their changes in physical and chemical properties.

Biological activity screening experiment: Using cell culture techniques, students are allowed to evaluate the inhibitory effects of different derivatives on tumor cell proliferation, and develop their experimental design and data analysis abilities. 

Preparation of methyl ethyl ketone (Ketone A):

Add acetone (90 g) into the beaker, then add methyl acetate (80 mL), sulfuric acid (4 mL), and stir at high speed. Add aluminum oxide (35 g) again, keep stirring at a high speed to avoid agglomeration, and then continue stirring with a magnetic stirrer for 30 minutes. Alumina was filtered off, and 160 mL of glacial acetic acid was added to the filtered solution. The obtained methyl ethyl ketone (Ketone A) was dried and cooled in a nitrogen stream to obtain 70 g of white crystals with a yield of 82.5%.

Synthesis of 3,4,5-methoxybenzaldehyde (Vanillin B):

3,4,5-Trimethoxybenzoic acid (10 g) was added to formaldehyde (2 mL), sodium hydroxide solution (3.6 g NaOH in 8 mL H2O) was added, and stirred for 30 min. The solution was transferred to a reflux device, stirred under reflux for 2 h, then the mixed liquid was acidified, and HCl (6N, in ice water) was added to pH = 1.0, and a white precipitate formed. After separation, washing and filtration, 3,4,5-methoxybenzaldehyde (Vanillin B) was obtained with a yield of 86.3%.

Preparation of compound K and other intermediates:

Mix methyl ethyl ketone (Ketone A, 8.19 g), 3,4,5-methoxybenzaldehyde (Vanillin B, 15 g) and butanone (25 mL), add chromium oxide (VI ) (6.8 g). The mixture was warmed from the ice bath to room temperature, and the reaction time was 2h. After the reaction mixture was uniformly mixed with water (75 mL) and formaldehyde (25 mL), sodium hydroxide (3.7 g) and hydrochloric acid Cl (6N, in ice water) were successively added until pH = 5.5, and a powdery white precipitate (compound K ). The precipitate was washed and dried to give 98% purity in 62% yield. Compound K (2.13g) and aldehyde (2.47g) were mixed, and ethanol (50 mL) was added, and sodium persulfite (Na2SO3, 1.29 g) was added to reduce the aldehyde, and the reaction time was 0.5h. Acetic acid (1.8 g) was added to remove impurities to give pink crystals (intermediate).

Preparation of Nortropinone Hydrochloride:

The obtained intermediate product, acetic acid (3 mL) and 10% HCl (10 mL) were mixed for a reaction time of 2 hours, filtered, extracted and dried to obtain it with a yield of 78%.

Overall, the synthesis of this is divided into four steps, the preparation of compound K and other intermediates is more complicated, but the overall yield can reach a higher level.

In summary, it is not only a structurally distinctive tropane alkaloid derivative but also a pivotal bridge connecting natural product chemistry, receptor pharmacology, and innovative drug development. Its unique bicyclic nitrogen heterocyclic structure, excellent physicochemical properties, and clear cholinergic regulatory mechanism make it irreplaceable in both fundamental research and pharmaceutical exploration. As a core tool molecule and versatile synthetic precursor, it continues to support in-depth studies on cholinergic system functions and the pathogenesis of related diseases. Moving forward, this will remain a key scaffold for designing safer and more selective neuroactive agents, providing sustained theoretical and material support for the discovery of new therapies in spasmolysis, neurodegenerative disorders, and central nervous system diseases.

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