AMINOPROPYLMORPHOLINE (APM)

Aminopropylmorpholine (APM), also known by its IUPAC name N-(3-Aminopropyl)morpholine, is a synthetic organic compound that contains both an amine group and a morpholine ring within its molecular structure, making it a bifunctional molecule that can participate in a wide range of chemical reactions.
Aminopropylmorpholine (APM)s structure consists of a morpholine ring—a six-membered heterocycle containing both nitrogen and oxygen atoms—attached to a three-carbon propyl chain that ends with a primary amine group (-NH₂).
Aminopropylmorpholine (APM) possesses a specific functional group that allows it to be recognized and internalized by lysosomes. 

CAS Number: 123-00-2
Molecular Formula: C7H16N2O
Molecular Weight: 144.21
EINECS Number: 204-590-2

Synonyms: 123-00-2, N-(3-Aminopropyl)morpholine, 3-Morpholinopropylamine, 3-morpholinopropan-1-amine, 4-MORPHOLINEPROPANAMINE, N-Aminopropylmorpholine, 4-(3-Aminopropyl)morpholine, 3-(morpholin-4-yl)propan-1-amine, 1-Amino-3-morpholinopropane, 4-Morpholinepropylamine, Morpholine, 4-(3-aminopropyl)-, (3-Aminopropyl)morpholine, 3-(4-Morpholinyl)-1-propanamine, 4-Aminopropylmorpholine, Morpholine, N-aminopropyl-, Morpholine, 4-aminopropyl-, 3-Morpholinopropanamine, gamma-Morpholinopropylamine, Aminopropylmorpholine, N-(3-Aminopropyl)morfolin, NSC 1081, .gamma.-Morpholinopropylamine, CHEBI:86554, N-(3-Aminopropyl)morfolin [Czech], EINECS 204-590-2, 3-(4-Morpholinyl)propylamine, 4-(3-aminopropyl)-morpholine, BRN 0105104, DTXSID4041521, AI3-52553, NSC-1081, 9A09425QD6, 1-morpholino-3-aminopropane, DTXCID2021521, 4-27-00-00411 (Beilstein Handbook Reference), 3-(N-MORPHOLINO)-1-AMINOPROPANE, 4-[3-Aminopropyl]morpholine, 3-(4-morpholinyl)propanamine, 4-(gamma-Aminopropyl)morpholine, 3-(MORPHOLINO)-N-PROPYLAMINE, 3-AMINO-1-(MORPHOLINO)PROPANE, Morpholine, 4-(3-aminopropyl)-(8CI), 204-590-2, InChI=1/C7H16N2O/c8-2-1-3-9-4-6-10-7-5-9/h1-8H, 3-morpholin-4-ylpropan-1-amine, 3-Morpholin-4-yl-propylamine, N-(3-aminopropyl)-morpholine, MFCD00006184, 3-morpholin-4-ylpropylamine, N-(3-aminopropyl) morpholine, CHEMBL158697, Morpholine, N-(3-aminopropyl)-, 4-(.gamma.-Aminopropyl)morpholine, 3-aminopropyl morpholine, UNII-9A09425QD6, NSC1081, N-(3-Aminopropyl)morpholine (AMP), NAPM, 3-aminopropylmorpholine, 3-morpholinylpropylamine, 3-morpholino-propylamine, N-(aminopropyl)morpholine, (3-morpholinopropyl)amine, 4-(aminopropyl)morpholine, bmse000971, bmse000981, 3-Morpholino-1-propylamine, 4-(3Aminopropyl)morpholine, N-(3-aminopropyl)morpholin, 3-morpholino-propan-1-amine, Oprea1_150673, SCHEMBL19922, WLN: T6N DOTJ A3Z, 3-morpholin-4-yl propylamine, MLS000556422, SCHEMBL948828, 3-morpholine-4-yl-propylamine, 4-(3-aminopropyl) morpholine, 3-Morpholinopropylamine, 98%, 4-(3-Aninopropyl)-morpholine, (3-morpholin-4-ylpropyl)amine, 3-(4-morpholinyl)-propanamine, 3-(morpholin-4-yl)propylamine, N-(gamma-aminopropyl)morpholine, SCHEMBL5345777, 3-Morpholinopropylamine, Liquid, SCHEMBL27687298, [3-(4-morpholinyl)propyl]amine, 3-(morpholin-4-yl)-propylamine, 3-(N-morpholinyl)-1-propylamine, 3-(4-morpholinyl)-1-propylamine, 3-(4-Morpholinyl)propan-1-amine, 3-morpholin-4-yl-propan-1-amine, HMS2384K03, 3-(4-morpholinyl)-1-aminopropane, 3-(4-morpholinyl)-propan-1-amine, STR02269, Tox21_302076, BDBM50607380, SBB028271, STK802951, 3-(4-Morpholinyl)-1-propanamine #, AKOS000119857, FD10554, NCGC00246332-01, NCGC00255491-01, CAS-123-00-2, FM160673, SMR000147739, A0409, CS-0008472, NS00019770, ST45255352, EN300-19625, Q27159240, F2187-2240, Z104474506, FC1F27D2-1429-41AC-9F03-C277D41006FA, Aminopropylmorpholine, gamma-Morpholinopropylamine, Morpholine, 4-(3-aminopropyl)-, Morpholine, 4-aminopropyl-, Morpholine, N-aminopropyl-, N-(3-Aminopropyl)morfolin, NAPM, N-AMINOPROPYL-MORPHLINE

Aminopropylmorpholine (APM)s unique structure allows it to act as a building block in the development of more complex molecules, particularly in medicinal chemistry where it can contribute to the design of novel drug candidates.
Aminopropylmorpholine (APM) is a versatile intermediate widely used in the chemical, pharmaceutical, and industrial manufacturing sectors. 
Aminopropylmorpholine (APM) functions effectively as a corrosion inhibitor, a neutralizing agent, and a chemical building block in the synthesis of more complex molecules. 

This property has been exploited by researchers to deliver various cargos, such as drugs, imaging probes, and nanoparticles, specifically to lysosomes. 
By delivering the cargo directly to lysosomes, researchers can achieve higher concentrations at the target site compared to untargeted delivery methods, potentially leading to improved therapeutic effects.

Targeting specific organelles like lysosomes can minimize the exposure of healthy cells to the cargo, potentially reducing side effects associated with systemic delivery.
Aminopropylmorpholine (APM) is a versatile compound widely utilized in various industrial and research applications. 
This amine derivative features a morpholine ring, which enhances its solubility and reactivity, making it an excellent candidate for use in the synthesis of pharmaceuticals, agrochemicals, and specialty chemicals. 

For instance, in water treatment processes, Aminopropylmorpholine (APM) is commonly used to prevent corrosion in boilers and pipelines, where its basicity and molecular size help it interact with metal surfaces and form protective films that reduce damage from acidic conditions.
Aminopropylmorpholine (APM) may discolor when exposed to air. 
Aminopropylmorpholine (APM) is also hygroscopic and will pick up moisture. 

If either of these two characteristics is not acceptable in the intended use of the product, it will be necessary to pad the storage tank.
Aminopropylmorpholine (APM) and its derivatives are useful as corrosion inhibitors. 
The reaction of Aminopropylmorpholine (APM) with d-butyrolactone gives an amber liquid useful as a corrosion inhibitor in lubricating oils and hydraulic uids. 

Organic salts of Aminopropylmorpholine (APM) are good corrosion inhibitors, sludge preventers, and color stabilizers in fuel oil. 
Aminopropylmorpholine (APM) itself is an eective corrosion inhibitor for steel in both synthetic and petroleum oil lubricants.
A copolymer of acrylic acid and methyl acrylate, reacted with Aminopropylmorpholine (APM) and the successive reaction products converted to the amide and quaternized with allyl r-toluene-sulfonate, produces a durable antistatic agent for textile nishes. 

Melt-spun lamentary material, especially nylon yarn, with improved dyeability and
adhesion properties is prepared by treatment in the undrawn state with Aminopropylmorpholine (APM).
Nonionic surface-active agents are prepared by reacting fatty acids, naphthenic acids, or rosin acids with Aminopropylmorpholine (APM), then adding alkylene oxides.

Soil conditioners can be prepared from Aminopropylmorpholine (APM) by conversion to substituted ammonium ions.
Treatment of clay soils with such compounds renders them permeable to uids and makes them stable toward disruption by either mechanical or chemical forces.
A cross-linked, weakly basic, anion-exchange resin can be made by reaction of Aminopropylmorpholine (APM) with a polymer made from an acrylic or methacrylic ester.

Reaction products of disubstituted Aminopropylmorpholine (APM) with an alkylene oxide are used as catalysts in the manufacture of polyurethanes which have no amine odor, even immediately after formation of the urethane.
Tertiary amine derivatives prepared by cyclocondensation of Aminopropylmorpholine (APM) with formaldehyde catalyzed the polymerization of toluene diisocyanate isomer mixtures to give an isocyanurate polymer and diol-toluene diisocyanate mixtures to give polyurethanes.
Pharmaceuticals useful as antiamebic agents, antihypertensives, inammation inhibitors, tranquilizers, and antithrombics are prepared from Aminopropylmorpholine (APM).

Aminopropylmorpholine (APM) is not typically used directly on skin or in cosmetics, its chemical stability, water solubility, and reactivity make it a valuable compound in the design of functional materials that require both hydrophilic and basic properties.
Aminopropylmorpholine (APM), also known as N-(3-aminopropyl)morpholine, is an organic compound characterized by its morpholine structure, which includes both an amine and an ether functional group. 

Aminopropylmorpholine (APM), among others are the key companies which presently operating in the global 3-Morpholinopropylamine (APM, CAS 123-00-2) market is predicted to develop during the forecast duration for leading the highest market growth, registering the great value of market share, obtaining the competitive edge, keep maintaining the governing position, leading the highest market growth and generating the highest percentage of revenue by improving the qualitative and quantitative measures of such, establishing the several research and development programs, employing the young and active personnel, decreasing the associated prices of such, spreading the awareness connected to the applications and advantages of 3-morpholinopropylamine, increasing the features and benefits of 3-morpholinopropylamine, analysing the strategies and policies of government as well as contenders and implementing the policies of profit making and strategies of expansion.

Melting point: −15 °C (lit.)
Boiling point: 224 °C (lit.)
Density: 0.987 g/mL at 25 °C (lit.)
Vapor density: 4.97
Vapor pressure: 11.5 Pa at 20 °C
Refractive index: n²⁰/D 1.4761 (lit.)
Flash point: 210 °F
Storage temperature: Keep in dark place, inert atmosphere, room temperature
Solubility: 1000 g/L
pKa: 10.30 ± 0.10 (Predicted)
Form: Liquid
Color: Colorless to almost colorless
pH: 12 (in H₂O at 20 °C)
Water solubility: Soluble
Sensitive: Air sensitive
BRN: 105104
LogP: −1.076 at 20 °C and pH 10.81–11.03
Surface tension: 70.3 mN/m at 1 g/L and 20 °C
Dissociation constant (Ka): 10.08

Aminopropylmorpholine (APM) is often used as a synthetic intermediate—that is, a starting material or stepping stone in the production of active pharmaceutical ingredients (APIs), pesticide molecules, or other biologically active compounds.
Aminopropylmorpholine (APM)s polar nature and flexible structure allow it to be incorporated into a wide range of chemical scaffolds, contributing to the development of new therapeutic agents or formulations.

Aminopropylmorpholine (APM) is also utilized in the formulation of specialty surfactants, textile chemicals, lubricants, and epoxy curing agents, where its reactive amine group can bind with acids, epoxides, or other active compounds to modify surface properties or improve adhesion. 
Aminopropylmorpholine (APM) plays a critical role in resin and polymer chemistry, where it helps to modify polymer backbones or improve cross-linking efficiency, resulting in enhanced mechanical strength, chemical resistance, or durability of coatings and adhesives.

Aminopropylmorpholine (APM) serves as a valuable ligand in coordination chemistry and catalysis, facilitating reactions that require specific molecular interactions. 
Its ability to form stable complexes with metal ions can be leveraged in various catalytic processes, enhancing reaction efficiency and selectivity. 
Researchers and industry professionals benefit from its multifunctional properties, which not only streamline synthetic pathways but also improve overall product yields. 

With its broad applicability, N-(3-Aminopropyl)morpholine stands out as a crucial component in advancing chemical research and development.
A colorless liquid with a faint, fishlike odor. Burns, but requires some effort to ignite. 
Produces toxic oxides of nitrogen during combustion.

Aminopropylmorpholine (APM) behaves as an amine. Amines are chemical bases. 
They neutralize acids to form salts plus water. 
These acid-base reactions are exothermic the amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base.

Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. 
Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.
Huntsman offers a wide range of electronic grade amines for applications in semiconductor formulated cleaning, etching, and stripping. 

This range of primary to quaternary amines offers formulators flexibility to tailor structure and performance to their needs. 
Several studies have demonstrated the successful application of 4-APM for lysosome-targeted delivery in various contexts, including.
Researchers have conjugated 4-APM to different therapeutic drugs to target specific lysosomal storage diseases, such as Gaucher disease and Niemann-Pick disease C.

Aminopropylmorpholine (APM) has been incorporated into fluorescent probes to visualize lysosomal activity and function in living cells.
Researchers have utilized Aminopropylmorpholine (APM) to deliver nanoparticles loaded with therapeutic agents or imaging probes to lysosomes.

Uses:
Aminopropylmorpholine (APM) is catalytic agent, petrochemical additive. 
Aminopropylmorpholine (APM) is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuffs.
One of the primary industrial uses of Aminopropyl Morpholine (APM) is as an effective corrosion inhibitor, especially in boiler water treatment systems, closed-loop cooling circuits, and steam distribution lines. 

Thanks to its basic amine group and polar morpholine ring, Aminopropylmorpholine (APM) can neutralize acidic byproducts such as carbonic acid (H₂CO₃) in steam condensate systems, thereby reducing the risk of metal corrosion and pipe degradation. 
Aminopropylmorpholine (APM) adsorbs onto metal surfaces and forms a protective molecular film, which acts as a barrier against moisture, oxygen, and corrosive ions, improving the operational lifespan of heat exchangers, pumps, and condensers.

Aminopropylmorpholine (APM) serves as a versatile chemical intermediate in the synthesis of various fine chemicals, pharmaceuticals, and agrochemicals, where it acts as a precursor or chain extender in the construction of more complex molecules. 
The reactive primary amine group on the propyl chain allows it to easily undergo acylation, alkylation, or condensation reactions, making it a useful building block in the development of active pharmaceutical ingredients (APIs) or pesticide formulations. 
For example, it may be used to create intermediates for antifungal agents, corrosion-resistant coatings, or even surface-active compounds.

In the field of polymer and coating chemistry, Aminopropylmorpholine (APM) is used as a curing agent or crosslinker for epoxy resins and polyurethane systems, where it improves the mechanical properties and chemical resistance of the final material. 
When used in these formulations, Aminopropylmorpholine (APM) helps to enhance flexibility, adhesion, and impact strength, which is especially important in applications such as industrial floor coatings, adhesives, and protective paints. Because of its small molecular size and high reactivity, Aminopropylmorpholine (APM) can penetrate polymer matrices and form dense cross-linked networks, leading to materials with superior durability and solvent resistance.

Aminopropylmorpholine (APM) is also used in the manufacture of specialty surfactants, particularly in textile finishing, leather processing, and cleaning agents, where its hydrophilic amine and morpholine functionalities allow it to act as a pH regulator, emulsifier, or dispersant. 
In textile chemicals, Aminopropylmorpholine (APM) can help modify the surface tension or absorbency of fibers, improving the performance of fabric softeners, dye carriers, or finishing agents.
Aminopropylmorpholine (APM)s ability to balance pH and interact with both hydrophilic and lipophilic substances makes it useful in cleaning formulations that require gentle yet effective cleaning power.

Although not typically used directly in consumer-facing drugs, Aminopropylmorpholine (APM) is frequently used in drug discovery and medicinal chemistry as a building block for molecular scaffolds. 
Its flexible structure and high solubility in water make it suitable for introducing basic nitrogen atoms into lead compounds or enhancing bioavailability in drug candidates.
Aminopropylmorpholine (APM) may be incorporated into experimental compounds designed for antiviral, anticancer, or antimicrobial screening, especially where the presence of a basic side chain is needed to interact with biological targets or transport proteins.

Aminopropylmorpholine (APM) is occasionally used as an additive in plasticizers, lubricants, or antistatic agents, where its ionic character can help to discharge static electricity or prevent material breakdown caused by friction and oxidation. 
In these applications, it serves a protective role, either by interacting chemically with the surface of the material or by modifying the electrical properties of polymers used in electronic housings, packaging, or mechanical components.

In the field of gas treatment and environmental engineering, Aminopropylmorpholine (APM) is being explored as a solvent or additive in carbon dioxide (CO₂) capture systems, especially those based on amine scrubbing technologies. 
Due to the presence of both a primary amine group and a heterocyclic morpholine ring, APM has a strong affinity for acidic gases such as CO₂ and H₂S. 
This allows it to react reversibly with CO₂ to form carbamate intermediates, which can then be regenerated under heat in a cyclic absorption–desorption process. 

As such, Aminopropylmorpholine (APM) is considered a candidate for improving the efficiency, stability, and capacity of amine-based carbon capture systems in power plants and chemical industries seeking to reduce greenhouse gas emissions.
In organic chemistry laboratories, Aminopropylmorpholine (APM) can also be used as a nucleophilic reagent or ligand in specialized synthetic reactions, where its bifunctional nature allows it to act in both hydrogen bonding and base-catalyzed transformations. 
Aminopropylmorpholine (APM) can be employed in reductive aminations, alkylation reactions, or Schiff base formations, where the primary amine group reacts with carbonyl-containing substrates. 

In some catalytic systems, its nitrogen lone pairs can coordinate with metal centers, serving as a chelating ligand in transition-metal-catalyzed transformations or polymer-supported catalysts.
While Aminopropylmorpholine (APM) itself is not typically used directly in cosmetic products due to its amine reactivity and potential for skin sensitivity at high concentrations, it is often used during ingredient development as part of the synthetic route for producing functional emulsifiers, quaternary ammonium surfactants, or conditioning agents. 
These downstream compounds are found in shampoos, conditioners, and hair treatments, where the original morpholine derivative has been chemically modified into non-irritating and more stable cationic surfactants that improve wet combing, shine, and hair manageability.

Safety Profile:
A corrosive material. Moderately toxic by several routes. 
A severe skin and eye irritant. 
Can react with oxidizing materials. 

To fight fire, use alcohol foam, dry chemical. When heated to decomposition it emits toxic fumes of NOx,.
Aminopropylmorpholine (APM) is classified as a corrosive or irritating substance, particularly in its pure or concentrated form, and can cause significant skin and eye irritation or burns upon contact. 
The primary amine group and morpholine ring contribute to the compound’s basicity and reactivity, which allows it to penetrate biological tissues and disturb cellular membranes, resulting in redness, pain, and inflammation. 

Exposure to the eyes may lead to serious damage, including corneal injury, if not flushed immediately with water. 
Therefore, it is essential to wear protective goggles, gloves, and lab coats when handling this compound in laboratory or industrial environments.
Inhalation of vapors, mists, or aerosols containing Aminopropylmorpholine (APM) may cause irritation to the respiratory tract, especially in poorly ventilated areas. 

Symptoms of exposure may include coughing, throat discomfort, chest tightness, or shortness of breath. 
In high concentrations, it can lead to inflammation of the mucous membranes of the nose and throat. 
Due to its alkaline vapor nature, prolonged inhalation may damage the lining of the respiratory tract, so local exhaust ventilation or appropriate respiratory protection (e.g., a respirator) is recommended when handling the material in large quantities or enclosed systems.

TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. 
Contact with molten substance may cause severe burns to skin and eyes. 
Avoid any skin contact effects of contact or inhalation may be delayed. 

Fire may produce irritating, corrosive and/or toxic gases. 
Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.
Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. 

Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). 
Contact with metals may evolve flammable hydrogen gas, containers may explode when heated.