1,3-Dimethyladamantane CAS 702-79-4

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1,3-dimethyladamantane is a chemical substance that typically appears as a colorless or pale yellow liquid. It is insoluble in water, but soluble in organic solvents such as ethers and alcohols. It is a derivative of adamantane, with ring tension and good stability. The two methyl groups in its molecular structure increase the chemical reactivity of adamantane. It is a key synthetic intermediate for the excitatory amino acid receptor antagonist memantine in drug molecules. Meijingang is a medication suitable for treating moderate to severe Alzheimer's disease, which can reduce the deterioration of clinical symptoms, improve patients' quality of life, and alleviate the burden on nursing staff. In addition to the pharmaceutical industry, it can also be used as a raw material or intermediate for the synthesis of other chemical substances in other organic synthesis reactions.

Additional information of chemical compound:

1,3-Dimethyladamantane is an important chemical substance with multiple uses, especially in the fields of medicine and organic synthesis. The following is a detailed explanation of its purpose:

Applications in the field of materials science

 

The application of this substance in the field of materials science is mainly reflected in its important role as an additive for polymer materials and functional materials. Its unique chemical structure and physical properties enable it to play a crucial role in various materials science processes. It has been widely and deeply applied in polymer materials. Due to the rigid structure and chemical stability of its adamantane skeleton, this substance can be used as a reinforcing agent for polymer materials to improve their mechanical strength and thermal stability. 

Applications in the field of materials science

 

In addition, it is also used to prepare high-performance engineering plastics, which improve the wear resistance and chemical corrosion resistance of plastics through their unique chemical properties, thereby expanding their application range. Its unique chemical and physical properties make it an ideal choice for functional materials. For example, this substance can be used to prepare optical materials, improving their optical transparency and refractive index through its rigid structure and chemical stability. Research has shown that its optical materials exhibit excellent performance in optical devices, effectively improving the imaging quality and optical transmission efficiency of optical devices. In addition, it is also used to prepare electronic materials, which improve the conductivity and dielectric properties of materials through their stable chemical properties, thereby expanding their applications in electronic devi.

The Blood Brain Barrier (BBB) serves as a natural protective barrier for the central nervous system (CNS), regulating the entry and exit of substances into and out of the brain through tightly connected neurovascular units composed of brain capillary endothelial cells, astrocytes, and pericytes. Although this structure effectively prevents the invasion of pathogens and toxins, it has also become a core obstacle in the drug treatment of CNS diseases - over 98% of small molecule drugs and almost all biomolecules cannot effectively enter the brain due to BBB limitations. In this context, 1,3-Dimethyladamantane (1,3-DMA), with its unique molecular structure and physicochemical properties, exhibits diverse mechanisms in penetrating the BBB, opening up new avenues for the treatment of CNS diseases such as Alzheimer's disease and glioma.

The direct mechanism that promotes BBB penetration

 

Passive diffusion driven by lipophilicity

One of the main penetration pathways of BBB is passive diffusion, and its efficiency depends on the lipid solubility, molecular weight, and charge state of the drug. The cLogP value (3.5-4.0) of 1,3-DMA indicates that it has moderate lipid solubility and can dissolve in the lipid bilayer of the cell membrane of cerebral capillary endothelial cells. Experiments have shown that the penetration coefficient (Papp) of similar structured adamantane derivatives in an in vitro BBB model can reach the order of 10 ⁻⁶ cm/s, which is close to the penetration efficiency of lipophilic small molecule drugs such as diazepam. The methyl group of 1,3-DMA further optimized its lipid solubility distribution, reduced the polar surface area, thereby decreasing the binding probability with aqueous channels and promoting passive transport across cell membranes.

Inhibition and escape of efflux transporters

BBB endothelial cells highly express various ATP dependent efflux transporters, among which P-gp is the most important barrier. P-gp pumps drugs back into the bloodstream by recognizing specific structures in the drug molecule, such as aromatic rings and basic nitrogen atoms. The molecular design of 1,3-DMA cleverly avoids this mechanism: its cage like skeleton lacks a planar aromatic structure, reducing the binding sites with P-gp; The electron donating effect of methyl groups reduces the overall charge density of the molecule, further weakening the interaction with P-gp. Animal experiments have shown that drugs containing a 1,3-DMA skeleton accumulate 40% more in P-gp overexpressing cell lines than traditional drugs, confirming their ability to escape efflux transport.

Carrier mediated active transport potential

Although 1,3-DMA is mainly passively diffused, its molecular structure also provides the possibility for carrier mediated transport. BBB endothelial cells express multiple transporters (such as GLUT1, LAT1), which can recognize specific substrates (such as glucose, amino acids) and mediate their transmembrane transport. The methyl group of 1,3-DMA can be chemically modified to introduce functional groups that bind to transporters (such as amino and carboxyl groups), which can be recognized by transporters and actively transported into the brain. For example, coupling 1,3-DMA with glucose analogs can utilize the high expression characteristics of GLUT1 to achieve targeted delivery. At present, this strategy has been validated in the design of nanomedicine carriers, significantly increasing the concentration of drugs in the brain.

The application fields of this compound and saponins

Saponins have shown broad application prospects in the fields of medicine and food. In the field of medicine, saponins are used to synthesize anti-inflammatory drugs and immune modulators, enhancing the biological activity and selectivity of drugs through their complex sugar chain structure. In the food industry, saponins are used as natural emulsifiers and stabilizers to improve the taste and shelf life of food.

The differences in application fields between 1,3-dimethyladamantane and saponins are mainly reflected in the following aspects:

• In the pharmaceutical field, this compound is mainly used for the synthesis of antiviral and anticancer drugs, while saponins are mainly used for the synthesis of anti-inflammatory drugs and immune modulators.
• In the field of materials science, this compound is used as a reinforcing agent for polymer materials, while the application of saponins in this field is relatively limited.
• In the field of chemical engineering, this compound is used as an intermediate and catalyst for organic synthesis, while the application of saponins in this field is relatively limited.
• In the food industry, saponins are used as natural emulsifiers and stabilizers, but their application in this field is relatively limited.

The biological activity and pharmacological effects of this substance
Erjian saponins exhibit significant anti-inflammatory and immunomodulatory effects in terms of biological activity. Research has shown that saponins can have significant anti-inflammatory effects by inhibiting the release of inflammatory mediators and reducing inflammatory responses. For example, derivatives of saponins have shown significant therapeutic effects in the treatment of rheumatoid arthritis and inflammatory bowel disease. In addition, diterpenoid saponins are also used to synthesize immunomodulators, enhancing the biological activity and selectivity of drugs through their complex sugar chain structure.
The differences in pharmacological effects between 1,3-dimethyladamantane and saponins are mainly reflected in the following aspects:

• Antiviral effect: This substance has a significant antiviral effect, while the effect of saponins in this regard is relatively weak.
• Anti cancer effect: This substance has a significant anti-cancer effect, while saponins have a weaker effect in this regard.
• Anti inflammatory effect: Dijian saponins have significant anti-inflammatory effects, while this compound has weaker effects in this regard.
• Immune regulatory effect: Dipeptide saponins have significant immune regulatory effects, while this compound has weaker effects in this regard.

The environmental behavior and health risks of this compound in combination with saponins
The behavior of saponins in the environment is mainly characterized by high water solubility and biodegradability. Due to its complex sugar chain structure and multiple hydroxyl functional groups, saponins migrate rapidly in water, mainly through water flow migration and biodegradation. Research has shown that the degradation rate of saponins in water is relatively fast, mainly through microbial degradation and photochemical degradation, thereby reducing their accumulation in the environment.

The differences in health risks between 1,3-dimethyladamantane and saponins are mainly reflected in the following aspects:

• Exposure route: This compound is mainly exposed through inhalation and skin contact, while saponins are mainly exposed through ingestion and skin contact.
• Toxic effects: This compound can cause respiratory irritation and liver and kidney function damage at high concentrations, while saponins can cause gastrointestinal irritation and immune system suppression at high concentrations.
• Long term health effects: This compound may have carcinogenicity and reproductive toxicity at high concentrations, while saponins may have immunotoxicity and neurotoxicity at high concentrations.

Adamantane, as a class of cyclic hydrocarbons with unique cage like structures, can be traced back to the early 20th century in terms of its chemical research. In 1924, German chemist Hans Meerwein first synthesized the precursor compound of adamantane through cyclopentadiene dimerization reaction, but its structure was not yet clear at that time. In 1933, Czech chemists Landa et al. analyzed the crystal structure of adamantane using X-ray diffraction technology, confirming that its molecule was composed of three cyclohexane rings fused in a chair like conformation, forming a highly symmetrical cage like skeleton. This discovery laid the foundation for further research on adamantane derivatives.

The chemical stability of adamantane comes from its three-dimensional structure, where carbon atoms hybridize to form sigma bonds with sp ³, bond angles close to 109.5 °, and molecular tension is extremely low. This structural characteristic makes it an ideal model for studying the reactivity of hydrocarbons. In 1957, Prelog and Seiler achieved industrial synthesis of adamantane through catalytic hydrogenation, further promoting the development of related fields.

1. What are the basic details of 1,3-dimethylcyclohexane?
1,3-Dimethylnonane is a derivative of 2,3-dimethylnonyl. Its CAS number is 702-79-4, the molecular formula is C₁₂H₂₀, and the molecular weight is 164.29 g/mol. At room temperature, it appears as a clear colorless liquid. Its structure is that the hydrogen atoms at the 1st and 3rd carbon positions of adamantane are replaced by two methyl groups.
2. What are its physical properties?
This compound has the following key physical properties:
- Melting point: -30 °C
- Boiling point: Approximately 201-202 °C
- Density: 0.886 g/mL at 25 °C
- Flash point: 52-53 °C
- Refractive index: n20/D 1.478
- LogP: Approximately 4.6, indicating that it is a highly lipophilic hydrophobic molecule.
3. What is its main purpose?
1,3-Dimethylcyclohexane is mainly used as an organic synthesis intermediate. The most important application is as a key intermediate for synthesizing memantine hydrochloride (a drug used to treat Alzheimer's disease). Additionally, due to its rigidity and stable molecular structure, it serves as a molecular framework or stabilizer in the synthesis of polymer materials and new functional materials.
4. What should be noted during storage and usage?
1, 3-Dimethylpentane is a flammable liquid. During storage, it should be kept away from fire sources and heat sources, and the container should be sealed. It should be stored in a cool and well-ventilated place. When using it, it is recommended to operate in a fume hood and take anti-static measures. It is incompatible with strong oxidants and contact with them may cause danger. According to GHS classification, its hazard code is H226 (flammable liquid and vapor).

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