Chem Explorers

The Versatile Applications of Allylamine: From Polymers to Pharmaceuticals

Allylamine: A Liquid and Stable Organic Compound

Allylamine is an organic compound with a chemical formula of C3H7NH2. It belongs to the class of alkene amines, which have an amino group (-NH2) attached to a carbon-carbon double bond (-C=C-).

Allylamine is a colorless to pale yellow liquid with a pungent odor. It is used in the production of various chemicals and as a building block for pharmaceuticals and agrochemicals.

In this article, we will explore allylamine identification, production, properties, and applications.

Allylamine Identification

CAS Number, ChemSpider, UNII, and ChEMBL

The Chemical Abstracts Service (CAS) number for allylamine is 107-11-9. It is used as an identifier in scientific databases and regulatory documents.

ChemSpider is a free chemical structure database that provides information on chemical properties, spectra, and patents. The ChemSpider ID for allylamine is 7515.

The Unique Ingredient Identifier (UNII) is a non-proprietary identifier for substances used in FDA drug labeling and other databases. The UNII for allylamine is 9EE14LG6LP.

The Chemical Biology and Drug Discovery Database (ChEMBL) is a resource for medicinal chemistry research. The ChEMBL ID for allylamine is CHEMBL511490.

Producing Allylamine and Chemical Formula

Allylamine can be synthesized in several ways, including the reaction of allyl chloride with ammonia, the reduction of allylamines, and the dehydrohalogenation of allyl halides. The most commonly used method involves the reaction of allyl chloride with an aqueous solution of ammonia and copper(I) as a catalyst.

The reaction produces allylamine and ammonium chloride as a byproduct. The chemical formula for allylamine is C3H7NH2.

It consists of three carbon atoms, seven hydrogen atoms, and one nitrogen atom. The carbon-carbon double bond and the amino group are attached to the second carbon atom from the end of the molecule, which is also known as the allylic position.

The allylic position imparts reactivity to the molecule, making it useful in a variety of applications.

Allylamine Properties

Physical and Chemical Properties

Allylamine is a flammable liquid with a boiling point of 55-56°C and a melting point of -70°C. It has a density of 0.854 g/cm3 and a refractive index of 1.429.

Allylamine is miscible with water and most organic solvents. It is a basic compound, with a pKa of 10.6, and forms salts with acids.

Allylamine is highly reactive due to the presence of the carbon-carbon double bond and the amino group. It can undergo various chemical reactions, including addition, substitution, and oxidation.

Toxicity and Safety

Allylamine is a corrosive and irritant substance that can cause severe burns and respiratory problems. It is toxic when ingested, inhaled, or absorbed through the skin.

Acute exposure to low concentrations can cause eye, throat, and lung irritation, while high concentrations can lead to pulmonary edema and chemical burns. Direct contact with allylamine should be avoided, and personal protective equipment should be worn when handling the substance.

Applications of Allylamine

Production of Polymers

Allylamine is used in the production of various polymers, such as polyallylamine, polyallylamine hydrochloride, and polyallylamine sulfate. These polymers have applications in water treatment, paper production, and drug delivery.

Polyallylamine hydrochloride, for example, is used as a flocculant in wastewater treatment and as a component in drug formulations.

Pharmaceuticals and Agrochemicals

Allylamine is a versatile building block for pharmaceuticals and agrochemicals. It is used in the synthesis of various drugs, such as antihistamines, antifungals, and anticancer agents.

Allylamine derivatives have been shown to possess antitumor, antiviral, and anti-inflammatory activities. Allylamine is also used to produce agrochemicals, such as herbicides and insecticides.

Surface Modification

Allylamine is used in surface modification techniques to modify the physical and chemical properties of substrates. For example, allylamine can be used to functionalize nanomaterials, such as gold nanoparticles, to improve their dispersion and stability in biological fluids.

Allylamine-coated substrates have also been shown to have antimicrobial properties, which can be useful in medical and environmental applications.

Conclusion

In this article, we have discussed allylamine identification, production, properties, and applications. Allylamine is a liquid and stable organic compound with a variety of applications in the chemical, pharmaceutical, and environmental industries.

As with any chemical substance, proper handling and safety measures should be observed when dealing with allylamine.

Physical and Chemical Properties of Allylamine

Allylamine is a colorless to pale yellow liquid with a pungent odor. It is soluble in water, ethanol, and ether.

Allylamine has a molar mass of 57.09 g/mol, a specific gravity of 0.854, a melting point of -70°C, and a boiling point of 55-56°C. It has a density of 0.848 g/mL and a vapor pressure of 151 mmHg at 25°C.

The chemical structure of allylamine consists of three carbon atoms, seven hydrogen atoms, and one nitrogen atom, arranged in a linear fashion. The nitrogen atom is attached to one of the carbon atoms via a single bond, while the other carbon atom is attached to the nitrogen atom via a double bond.

This configuration creates a reactive allylic position that makes allylamine chemically versatile.

Allylamine Reactions

Polymerization and Poly(Allylamine Hydrochloride)

Allylamine undergoes polymerization reactions to form various polymeric materials. One example is poly(allylamine hydrochloride) (PAH), which is synthesized by the polymerization of allylamine with hydrochloric acid (HCl) as a counterion.

PAH is a cationic polyelectrolyte that has applications in various fields such as biomedical engineering and water treatment. In biomedical engineering, PAH is used as a coating material for drug delivery, gene therapy, and tissue engineering.

In water treatment, PAH is used as a flocculant to remove suspended particles and pollutants from wastewater. The properties of PAH can be tailored by adjusting the polymerization conditions, such as the pH, temperature, and initiator concentration.

Cell Encapsulation

Another application of allylamine polymerization is in cell encapsulation. Cell encapsulation is a technique that involves enclosing living cells within a polymer matrix.

The polymer matrix protects the cells from the immune system of the host and allows the controlled release of therapeutic substances. Allylamine can be polymerized with other monomers, such as acrylamide and N,N’-methylenebisacrylamide, to form hydrogels that can encapsulate cells.

These hydrogels provide a three-dimensional environment for the cells to grow and function. The properties of the hydrogels, such as the stiffness, porosity, and swelling behavior, can be tailored to suit the specific needs of the application.

Isomerization to Produce Aldimine

Allylamine can undergo isomerization reactions to produce aldimines. Aldimines are a class of organic compounds that contain a carbon-nitrogen double bond (C=N) and a carbon-oxygen double bond (C=O).

The isomerization reaction involves the migration of a hydrogen atom from the allylic position to the nitrogen atom, resulting in the formation of an aldimine. Aldimines have applications in organic synthesis and materials science.

For example, aldimines can be used as intermediates in the synthesis of pharmaceuticals, agrochemicals, and polymers. Aldimines can also be incorporated into polymers to introduce specific properties, such as self-healing and stimuli-responsiveness.

Conclusion

Allylamine is a versatile compound with a range of physical and chemical properties that make it useful in many applications. Allylamine can be polymerized to form materials with specific properties, such as cationic polyelectrolytes and hydrogels for cell encapsulation.

Allylamine can also undergo isomerization reactions to produce aldimines, which have applications in organic synthesis and materials science. Proper handling and safety measures should be observed when dealing with allylamine, as it is a corrosive and toxic substance.

Applications of Allylamine

Industrial Uses as a Chemical Solvent

Allylamine is used as an industrial chemical solvent in various processes, such as polymerization, chlorination of hydrocarbons, and extraction of metals from ores. It is also used as a co-monomer in the production of resins, plastics, and elastomers.

Allylamine’s solubility and reactivity make it a versatile solvent in many applications. For example, allylamine is used as a solvent for catalysts in the production of polyurethane foams, as a swelling agent for pressure-sensitive adhesives, and as a stabilizer for emulsions.

Medical Uses as Antifungal and Antibiotic Medicine

Allylamine has medical uses as an antifungal and antibiotic agent. Allylamines inhibit the biosynthesis of sterols in fungi and bacteria, leading to cell membrane damage and growth inhibition.

The most commonly used allylamine in medicine is terbinafine, which is used to treat fungal infections of the skin, nails, and hair. Terbinafine is available in various forms, such as creams, gels, and tablets.

Another allylamine used in medicine is Naftifine, which is used to treat athlete’s foot and jock itch.

Allylamine Material Safety Data Sheet (MSDS)

Toxicology and First Aid Measures

Allylamine is a corrosive and toxic substance that can cause severe burns and respiratory problems. Exposure to allylamine can cause irritation to the skin, eyes, and respiratory system.

It can also cause pulmonary edema and chemical burns. Inhalation of allylamine vapors can cause coughs, difficulty breathing, and shortness of breath.

Ingestion of allylamine can cause abdominal pain, nausea, and vomiting. In case of exposure to allylamine, the following first aid measures should be taken:

  • Skin contact: Immediately remove contaminated clothing and rinse skin with plenty of water for at least 15 minutes. Seek medical attention if irritation or blistering occurs.
  • Eye contact: Rinse eyes with water for at least 15 minutes, lifting the eyelids occasionally. Seek medical attention if irritation persists.
  • Inhalation: Move to an area with fresh air. If breathing is difficult, give oxygen. Seek medical attention if symptoms persist.
  • Ingestion: Do not induce vomiting. Give milk or water to drink. Seek medical attention immediately.

Personal Safety Measures, Storage Instructions, Fire Fighting Measures, and Accidental Release Measures

Personal safety measures should be observed when handling allylamine.

Protective clothing, gloves, and goggles should be worn to prevent contact with the skin, eyes, and respiratory system. Allylamine should be stored in a cool, dry, and well-ventilated area away from heat, sparks, and flames.

Containers of allylamine should be properly labeled with hazard warnings and kept tightly closed. In case of a fire involving allylamine, water, dry chemical powder, or carbon dioxide should be used as extinguishing agents.

Allylamine can produce toxic fumes when heated or burned, so firefighters should wear self-contained breathing apparatus. In the event of an accidental release of allylamine, the following measures should be taken:

  • Evacuate the area and restrict access to the spill site.
  • Wear protective clothing and equipment.
  • Contain the spill with absorbent materials, such as sand or vermiculite.
  • Transfer the spill to containers for proper disposal.
  • Decontaminate the area with soap and water.

Conclusion

Allylamine has numerous industrial and medical applications, making it a valuable compound in various fields. It is used as a chemical solvent and co-monomer in industrial processes and as an antifungal and antibiotic agent in medicine.

However, it is also a toxic and corrosive substance that requires proper handling and safety measures. Material safety data sheets provide guidelines for the safe handling and disposal of allylamine.

Allylamine Brand Names and Suppliers

Allylamine, specifically in the form of terbinafine, is widely used in the pharmaceutical industry to treat fungal infections of the skin, nails, and hair. It is available under various brand names as skin creams and pills, offering patients a choice of treatment options.

Additionally, allylamine is distributed by worldwide suppliers, ensuring the availability of these medications to patients in different countries.

Brand Names for Skin Creams and Pills

Terbinafine, which is an allylamine antifungal medication, is marketed under different brand names worldwide. Some of the commonly recognized brand names include:

  1. Lamisil: Lamisil is one of the most well-known brand names for terbinafine. It offers a range of products, including creams, sprays, and tablets. Lamisil products are available in many countries and are easily accessible to patients seeking relief from fungal infections.
  2. Terbinex: Terbinex is another brand that offers terbinafine-based creams and ointments. It is known for its effectiveness in treating various dermatological conditions caused by fungal infections.
  3. Terbisil: Terbisil is a brand name that offers terbinafine in cream and spray formulations. It is widely available in pharmacies and provides effective relief for patients suffering from fungal infections.
  4. Sebifin: Sebifin is a brand name that offers terbinafine in oral tablet form. It is used to treat fungal infections of the skin and nails. Sebifin tablets are an effective option for patients who prefer oral medication for their condition.

These are just a few examples of the brand names under which allylamine-based products are marketed. It is important to note that the availability and brand names may vary across different countries and regions.

Worldwide Suppliers

Allied with the rising demand for terbinafine-based products, there are several global suppliers that ensure the availability of these medications around the world. Some of the key suppliers include:

  1. Novartis: Novartis, a multinational pharmaceutical company headquartered in Switzerland, is a major supplier of terbinafine-based medications. Novartis markets its products under the brand name Lamisil and ensures wide distribution to pharmacies worldwide.
  2. Cipla: Cipla, an Indian multinational pharmaceutical and biotechnology company, is also a significant supplier of allylamine-based products. Cipla manufactures and markets terbinafine products under various brand names, providing accessibility in different regions.
  3. Mylan: Mylan, a global generic and specialty pharmaceutical company, offers terbinafine-based medications under different brand names. Mylan’s extensive distribution network ensures that patients have access to these products in various countries.
  4. Teva: Teva Pharmaceutical Industries, an Israeli multinational pharmaceutical company, is another important allylamine supplier. Teva manufactures and distributes terbinafine-based medications to cater to the needs of patients worldwide.

These are just a few examples of the worldwide suppliers of allylamine-based medications. The pharmaceutical industry is vast, and there are numerous companies involved in the production and distribution of these products. Local suppliers and generic alternatives also play a crucial role in providing cost-effective options to patients.

In conclusion, allylamine is widely used in the pharmaceutical industry for the treatment of fungal infections. Brand names such as Lamisil, Terbinex, Terbisil, and Sebifin offer patients a variety of options in the form of skin creams and pills.

Global suppliers, including Novartis, Cipla, Mylan, and Teva, ensure the availability of these medications worldwide. It is important to consult healthcare professionals and follow their guidance when choosing and using allylamine-based products.

In conclusion, allylamine, a liquid and stable organic compound, finds diverse applications in various industries and medical fields. Its identification, physical and chemical properties, reactions, and safety measures are important to understand.

Allylamine is used as a chemical solvent in industries and as an antifungal and antibiotic medicine in the medical field. Brand names like Lamisil, Terbinex, Terbisil, and Sebifin offer different forms of allylamine treatments, while global suppliers such as Novartis, Cipla, Mylan, and Teva ensure its availability.

Allylamine’s versatility and significance underscore its importance in both industrial and healthcare settings. It is essential to prioritize safety measures and closely follow medical guidance when using allylamine products.

FAQs:

  1. Q1: What are the industrial uses of allylamine? A1: Allylamine serves as a chemical solvent, co-monomer in resin production, and catalyst in polymerization reactions.
  2. Q2: How is allylamine used in medicine? A2: Allylamine, particularly in the form of terbinafine, is used as an antifungal and antibiotic medicine to treat various fungal infections of the skin, nails, and hair.
  3. Q3: Which brand names offer allylamine-based treatments? A3: Some commonly known brand names include Lamisil, Terbinex, Terbisil, and Sebifin, available in the form of creams, ointments, sprays, and tablets.
  4. Q4: Who are the worldwide suppliers of allylamine-based medications? A4: Global suppliers such as Novartis, Cipla, Mylan, and Teva ensure the distribution and availability of allylamine products across different regions.
  5. Q5: What precautions should be taken when handling allylamine? A5: Protective clothing, gloves, and goggles should be worn, and proper storage, fire-fighting, and accidental release measures should be followed due to the corrosive and toxic nature of allylamine.

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