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Dimethylethanolamine

Dimethylethanolamine (DMAE), also known as 2-(dimethylamino)ethanol, is a versatile organic compound with the chemical formula C₄H₁₁NO and a molecular weight of 89.14 g/mol.^[1] It appears as a clear, colorless liquid with a strong amine-like or fishy odor, exhibiting a boiling point of 134–136 °C, a melting point of -70 °C, a flash point of 105 °F (41 °C), and a density of 0.886 g/cm³ at 20 °C; it is fully miscible with water and many organic solvents.^[1]^[2] As a beta-amino alcohol, DMAE serves as a key building block in chemical synthesis, bridging the properties of alcohols and amines, and is produced industrially by the reaction of ethylene oxide with dimethylamine under controlled pressure and temperature conditions.^[3] DMAE finds widespread industrial applications, particularly as a curing agent and catalyst in the production of polyurethane foams (both flexible and rigid), epoxy resins, and amino resins, as well as in the formulation of water-based paints, lacquers, surface coatings, and ion-exchange resins.^[3] It acts as a chemical intermediate for synthesizing pharmaceuticals, dyestuffs, textiles, emulsifiers, corrosion inhibitors (including in steel-reinforced concrete), and flocculants for wastewater treatment.^[2]^[4] In consumer products, DMAE is incorporated into cosmetics and skincare formulations as a buffering agent and skin-firming ingredient (often as the bitartrate salt at concentrations up to 3%), and it has been explored for cognitive-enhancing supplements due to its natural occurrence in foods like fish.^[3] Additionally, it is approved by the FDA for use as a secondary direct food additive in processes like beet and cane sugar clarification.^[5] Despite its utility, DMAE is classified as a flammable liquid (Category 3), corrosive to skin and eyes (Category 1), and acutely toxic if inhaled or swallowed (Categories 3/4), with vapors heavier than air that may travel to ignition sources and flash back.^[1]^[6] It reacts violently with strong oxidizers, acids, acid chlorides, and isocyanates, potentially generating toxic nitrogen oxides during combustion.^[2] Exposure can cause severe irritation or burns to mucous membranes, respiratory tract, and skin; chronic effects may include asthma-like allergies or nervous system impacts, with no established occupational exposure limits but recommendations for ventilation and personal protective equipment in handling.^[1]^[2] Toxicity data indicate an oral LD50 of 1,182 mg/kg in rats and potential absorption through the skin.^[1]

Chemistry

Structure and nomenclature

Dimethylethanolamine has the chemical formula C₄H₁₁NO, commonly represented as (CH₃)₂NCH₂CH₂OH.^[7] Its IUPAC name is 2-(dimethylamino)ethanol. Common synonyms include deanol, DMEA, N,N-dimethylaminoethanol, and N,N-dimethylethanolamine. This compound is classified as an amino alcohol, characterized by a tertiary amine functional group (-N(CH₃)₂) and a primary alcohol functional group (-CH₂OH) separated by an ethylene (-CH₂CH₂-) bridge. The linear arrangement of these groups imparts bifunctional reactivity while maintaining a simple, non-branched carbon skeleton.^[7] The molecular weight of dimethylethanolamine is 89.14 g/mol.^[7] As an achiral molecule lacking a stereogenic center, it exhibits no optical isomers.

Physical and chemical properties

Dimethylethanolamine is a colorless, viscous liquid at room temperature, exhibiting a characteristic fishy or amine-like odor. It has a boiling point of 134–136 °C and a melting point of −59 °C, remaining liquid over a wide temperature range under ambient conditions.^[1]^[8] The density is 0.886 g/cm³ at 20 °C, making it less dense than water.^[1] The compound is miscible with water, ethanol, ether, acetone, and benzene, reflecting its amphiphilic nature due to the polar hydroxyl and amine groups. In aqueous solutions at 100 g/L, it produces a pH of 10.5–11, consistent with its basic character.^[1] Chemically, dimethylethanolamine functions as a weak base owing to its tertiary amine group, with the pKa of the conjugate acid being 9.26 at 25 °C.^[9] The alcohol group is weakly acidic, with a pKa of approximately 15.6. It exhibits nucleophilic behavior at both the nitrogen and oxygen atoms, readily forming salts with acids and esters under appropriate conditions.^[10] The compound reacts vigorously with strong oxidizing agents, potentially leading to oxidation of the alcohol to an aldehyde or carboxylic acid, and it is stable under normal storage but incompatible with acids and isocyanates.^[1]

Production

Synthesis methods

Dimethylethanolamine was first synthesized in the early 20th century through the reaction of ethylene oxide with dimethylamine, marking an early application of epoxide ring-opening chemistry in organic synthesis.^[11] The primary laboratory method for producing dimethylethanolamine involves the nucleophilic addition of dimethylamine to ethylene oxide, yielding the desired product via ring-opening of the epoxide.

(\ce{CH3})_2\ce{NH} + \ce{C2H4O} \rightarrow (\ce{CH3})_2\ce{NCH2CH2OH}

This reaction proceeds under equimolar stoichiometry, with excess dimethylamine often employed to minimize side reactions.^[4]^[12] Alternative synthetic routes include the substitution reaction of 2-chloroethanol with dimethylamine, which generates the product along with hydrochloric acid as a byproduct. This method requires careful control to avoid elimination side reactions. Another approach utilizes reductive amination of glycolaldehyde with dimethylamine, typically employing hydrogen gas and a metal catalyst such as nickel or ruthenium to facilitate imine reduction, offering a bio-based pathway from sugar-derived feedstocks.^[13]^[14] These syntheses are generally conducted in aqueous or alcoholic solvents at moderate temperatures ranging from 50 to 100 °C, with pressures up to several atmospheres to maintain reactants in the liquid phase. Yield optimization involves adjusting the amine-to-epoxide ratio (typically 3:1 to 6:1 molar excess of dimethylamine) to suppress side products such as bis-substituted amines like N,N,N-trimethylethylenediamine from over-alkylation or polymerized ethylene oxide oligomers.^[15]^[16]^[14]

Commercial manufacturing

Dimethylethanolamine (DMEA) is commercially produced through a continuous reaction of dimethylamine and ethylene oxide in pressurized reactors, typically operating under elevated temperatures and pressures to achieve high yields.^[15] The process involves feeding anhydrous dimethylamine and ethylene oxide into successive mixing reactors, followed by displacement under controlled conditions to form the product.^[15] Purification is accomplished via distillation, often with acid treatment to remove impurities and recover DMEA as a high-purity distillate fraction.^[17] Global production is estimated at approximately 250,000 tonnes per year as of the 2020s, with historical U.S. output reported at 22,700–45,400 tonnes in 1998; as of 2024–2025 market reports indicate sustained or growing volumes driven by demand in polyurethane and coatings sectors.^[18]^[4]^[19] Major producers as of 2024 include BASF, Dow Chemical Company, Huntsman Corporation, Eastman Chemical Company, and Mitsubishi Gas Chemical, with additional manufacturing by companies such as Jintan Dingsheng Chemical in Asia.^[19] Cost factors in DMEA manufacturing are influenced by raw material sourcing, as dimethylamine is derived from the catalytic reaction of methanol and ammonia, while ethylene oxide is produced via petrochemical routes; fluctuations in these inputs, along with energy demands for high-pressure reactions and waste management from byproducts like water and unreacted amines, significantly affect overall economics.^[20]^[21] Quality control emphasizes achieving purity levels exceeding 99%, with strict limits on impurities such as water (maximum 0.2 wt%), dimethylamine, and side products like methyldiethanolamine or dimethyldiglycolamine (collectively under 0.7 wt%).^[22] Recent developments include shifts toward greener processes, such as the integration of bio-based ethylene oxide derived from renewable ethanol via dehydration and epoxidation, enabling reduced carbon footprints in production post-2020.^[23] Innovations like electrochemical oxidation of ethylene for ethylene oxide synthesis further support sustainable manufacturing by minimizing energy use and emissions.^[24]

Applications

Industrial uses

Dimethylethanolamine (DMEA) serves as a key catalyst in the production of polyurethane foams, both flexible and rigid varieties. It accelerates the reaction between polyols and isocyanates, promoting both the blowing (gas-forming) and gelling (polymerization) processes to enhance foam rise, structure, and curing efficiency. Typical dosages range from 0.5 to 2% by weight of the polyol component, allowing for balanced reaction control and improved foam properties such as density and thermal insulation.^[25] In the paints and coatings industry, DMEA functions as an emulsifier, dispersant, and pH adjuster in water-based formulations. Its water solubility aids in neutralizing acidic resins, stabilizing emulsions, and improving pigment dispersion, which results in better paint flow, reduced settling, and enhanced film formation. This role is particularly valuable for acrylic and epoxy-based coatings, where DMEA contributes to viscosity control and overall product performance.^[26]^[27] DMEA is widely employed in water treatment as a corrosion inhibitor and neutralizing agent in boiler systems and cooling waters. It buffers pH levels to counteract acidic components, preventing scale formation and metal degradation in industrial equipment. It is also approved by the FDA as a secondary direct food additive for use in clarifying beet and cane sugar.^[5] Global annual demand for DMEA is estimated at around 100,000–110,000 tons.^[4] Additional industrial applications include its use as an additive in fabric softeners for textiles, where it imparts softness and reduces static cling during finishing processes; as a curing agent and stabilizer in adhesives, enhancing cross-linking, shear strength (up to 40% improvement), and heat resistance (up to 30% higher); and as a solvent or viscosity modifier in inks to optimize printing characteristics. Polyurethane-related uses account for approximately 25%–30% of DMEA consumption, with paints and coatings representing the largest segment at 35%–40%, with global market growth projected at approximately 5.5%–7% CAGR from 2024 to 2032 (as of 2025 reports), supported by recent capacity expansions such as BASF's new plant in 2024.^[28]^[29]^[30]^[31]^[32]

Pharmaceutical and medical uses

Dimethylethanolamine, also known as deanol, was introduced in the 1950s as a prescription medication under the brand name Deaner by Riker Laboratories for treating behavioral and learning disorders in children, particularly attention deficit-hyperactivity disorder (ADHD) and cognitive impairments.^[33] Marketed as a nootropic, it was claimed to enhance brain function by serving as a precursor to acetylcholine, a neurotransmitter involved in memory and attention.^[34] Promotional efforts by pharmaceutical companies highlighted its potential for improving focus and reducing hyperactivity, leading to widespread use through the 1960s and 1970s.^[4] Clinical studies in the 1970s, however, increasingly questioned its efficacy, with trials showing limited or no benefits compared to placebo or standard treatments like methylphenidate.^[35] For example, a double-blind study in children with minimal brain dysfunction found deanol produced no significant improvements in behavior or cognition, contributing to a decline in its medical acceptance.^[36] In 1983, the U.S. Food and Drug Administration (FDA) withdrew approval for Deaner, citing insufficient evidence of therapeutic effectiveness from post-marketing studies.^[37] Historical oral dosages typically ranged from 300 to 600 mg per day, administered in tablet form.^[38] As a pharmaceutical intermediate, dimethylethanolamine is utilized in the synthesis of various active pharmaceutical ingredients, including antibiotics, antihistamines, analgesics, and certain anticholinergics such as procyclidine.^[39] Its role in these processes involves providing a dimethylamino functional group essential for drug molecule assembly.^[40] Currently, deanol is no longer approved as a prescription drug in FDA-regulated markets but remains available as a dietary supplement in some regions, though with regulatory scrutiny due to prior efficacy concerns.^[33] Its medical applications are now largely limited to topical formulations in cosmetics, where it is employed for potential skin-firming effects at concentrations typically below 5%.^[41] In pharmaceutical manufacturing, it continues to be used exclusively as a synthetic precursor rather than a direct therapeutic agent.^[26]

Biological effects and safety

Pharmacological profile

Dimethylethanolamine (DMAE), also known as deanol, is proposed to exert its pharmacological effects primarily through its role as a precursor to choline and acetylcholine, thereby potentially enhancing cholinergic neurotransmission in the brain at low doses.^[42] This mechanism involves DMAE crossing the blood-brain barrier more readily than choline itself, where it may be methylated to support acetylcholine synthesis and contribute to phosphatidylcholine production via intermediate phosphatidyldimethylethanolamine pathways.^[43] Additionally, DMAE functions as a weak cholinergic agonist, influencing neuronal excitability and potentially altering muscle contraction by mimicking acetylcholine effects.^[44] DMAE is rapidly absorbed following oral administration, with studies in rodents showing 21–44% retention in tissues within 24 hours, indicating efficient uptake and distribution to the liver and brain.^[43] Once absorbed, it undergoes hepatic metabolism, primarily forming the N-oxide metabolite and N,N-dimethylglycine, with a substantial portion (up to 33% in humans) excreted unchanged in urine.^[45] The elimination half-life exceeds 30 hours after dermal exposure, though plasma kinetics suggest shorter clearance times in systemic circulation.^[4] Early research from the 1960s to 1980s, including studies by Ban and Lehmann, reported mixed results on DMAE's impact on mood and cognition, with some evidence of improved alertness and attention in hyperkinetic children but inconsistent benefits for overall psychiatric symptoms.^[46] Animal studies have demonstrated that DMAE elevates brain levels of the compound itself and choline, yet findings on behavioral outcomes, such as memory enhancement in radial arm maze tasks, lack consistency across models, showing no reliable improvements in scopolamine-induced deficits or other cognitive measures.^[47] Modern reviews and analyses from the 2010s, evaluating nootropic applications, conclude a lack of robust efficacy for cognitive or mood enhancement due to methodological limitations in prior trials and insufficient high-quality evidence. Reviews as of 2022 continue to find insufficient high-quality evidence supporting DMAE's efficacy for cognitive enhancement.^[47] Regarding interactions, DMAE may exhibit synergy with choline supplements by augmenting precursor availability for acetylcholine synthesis, potentially amplifying nootropic effects in combination therapies.^[34] However, it is contraindicated with monoamine oxidase inhibitors (MAOIs), as co-administration can provoke adverse reactions including insomnia, headache, tremor, or hypomania through enhanced neurotransmitter activity.

Toxicity and health risks

Dimethylethanolamine (DMAE) exhibits acute toxicity primarily through its corrosive and irritant properties. It causes severe skin burns, eye damage, and respiratory irritation upon contact or inhalation, with symptoms including redness, pain, blistering, coughing, and potential pulmonary edema. The oral LD50 in rats is 1,182 mg/kg, indicating moderate acute oral toxicity, while the dermal LD50 in rabbits is 1.37 g/kg.^[1]^[48] Chronic exposure to high doses of DMAE may lead to neurotoxic effects, including overstimulation of the nervous system. Reports from supplement use associate it with insomnia, muscle tension, headaches, and sporadic hyperactivity, potentially linked to enhanced cholinergic or catecholaminergic activity at elevated levels.^[49]^[50] No specific OSHA PEL has been established for DMAE. NIOSH recommends a REL of 1 ppm (10 mg/m³) as an 8-hour TWA and 2 ppm (21 mg/m³) STEL. Inhalation above these levels can exacerbate respiratory symptoms such as coughing and delayed pulmonary edema.^[4] DMAE has not been evaluated or classified by IARC with regard to its carcinogenicity to humans. Reproductive toxicity studies, including prenatal developmental assessments in rats, show no significant adverse effects on reproduction or fetal development at doses up to 1,000 mg/kg/day, with only equivocal evidence of minor skeletal variations.^[51]^[52] For first aid, immediate flushing with water for at least 15 minutes is recommended for skin or eye exposure to minimize burns and damage; seek medical attention promptly. In cases of ingestion, do not induce vomiting; provide supportive care including monitoring for respiratory distress and gastrointestinal effects under professional supervision.^[53]^[54]

Environmental and regulatory aspects

Environmental fate

Dimethylethanolamine (DMEA) demonstrates low persistence in the environment due to its ready biodegradability under aerobic conditions. In ready biodegradability tests conducted with activated sludge inoculum, DMEA achieved 67% degradation after 10 days and exceeded 60% of the theoretical oxygen demand within 14 days, confirming its rapid breakdown by sewage microorganisms following an initial adaptation period.^[55] The compound does not undergo significant hydrolysis at neutral pH typical of natural waters, as it lacks hydrolyzable functional groups, but its atmospheric half-life is short at approximately 4.6 hours, primarily through reaction with hydroxyl radicals.^[56] In soil and sediment, DMEA is not expected to persist owing to its high water solubility and low adsorption potential, with model predictions indicating quick dissipation through biodegradation rather than accumulation.^[55] DMEA has low bioaccumulation potential in organisms, attributed to its hydrophilic nature and measured octanol-water partition coefficient (log Kow) of -0.55.^[57] This negative log Kow value suggests minimal partitioning into lipids, resulting in low bioconcentration factors (BCF ≈ 3 L/kg wet weight) across aquatic species, and it is unlikely to biomagnify in food chains.^[57] Ecotoxicological assessments indicate moderate toxicity of DMEA to aquatic life, with effects observed at concentrations relevant to industrial releases. For fish, the 96-hour LC50 is 147 mg/L in golden orfe (Leuciscus idus), reflecting acute lethality through gill irritation and osmoregulatory disruption. Invertebrates such as Daphnia magna exhibit a 48-hour EC50 of 230 mg/L, while algae (Scenedesmus subspicatus) show growth inhibition with a 72-hour EC50 of 414 mg/L, primarily impacting photosynthesis and cell division at higher exposures. These values classify DMEA as harmful to aquatic organisms but not highly toxic, with no observed chronic effects at environmentally relevant levels below 1 mg/L. Primary release sources of DMEA to the environment include industrial effluents from polyurethane foam production, paint manufacturing, and water treatment processes, where it is used as a catalyst or neutralizer and enters wastewater streams.^[4] Regulatory information current as of 2023 per ECHA.^[58]

Regulations and handling

Dimethylethanolamine (DMEA) is classified as a hazardous substance under the European Union's Classification, Labelling and Packaging (CLP) Regulation, with harmonized classifications including Skin Corr. 1B (causes severe skin burns and eye damage), Eye Dam. 1, Acute Tox. 4 (harmful if swallowed, in contact with skin, or inhaled), and Flam. Liq. 3 (flammable liquid and vapor).^[58] It is registered under the REACH Regulation (EC) No 1907/2006, subjecting it to general obligations for manufacturers and importers, including safety data provision and risk assessments, though no specific entry restricts it under Annex XVII.^[58] In the United States, DMEA is listed on the Toxic Substances Control Act (TSCA) Inventory, requiring reporting for certain activities but imposing no outright bans on its use.^[59] Handling guidelines emphasize safe storage and use to mitigate its corrosive and flammable properties. DMEA should be stored in a cool, dry, well-ventilated area away from incompatible materials such as strong oxidizers, acids, and sources of ignition, using tightly sealed containers to prevent vapor buildup.^[60] Personal protective equipment (PPE), including chemical-resistant gloves, safety goggles, and protective clothing, is required during handling to avoid skin and eye contact.^[61] For spill response, non-combustible absorbent materials like sand or vermiculite should be used to contain and neutralize the liquid, followed by proper ventilation and disposal as hazardous waste in accordance with local regulations.^[60] Transportation of DMEA is regulated internationally under the United Nations (UN) system as UN 2051, classified as a Class 8 corrosive substance with a subsidiary Class 3 flammable liquid hazard, assigned to Packing Group II (medium danger).^[62] Proper labeling includes corrosive and flammable pictograms, along with hazard statements, and it must be packaged in approved corrosion-resistant containers to prevent leaks during shipment by road, rail, sea, or air.^[61] Regulatory variations exist across jurisdictions, particularly in consumer products. In the United States, DMEA was withdrawn from the market as a prescription drug in 1983 by the Food and Drug Administration (FDA) due to insufficient evidence of efficacy for conditions like attention deficit disorder, though it remains available as an unregulated dietary supplement without FDA approval for any health claims.^[33] In the European Union, under the Cosmetics Regulation (EC) No 1223/2009, DMEA is permitted in cosmetic products subject to general safety requirements and risk assessments due to its irritant potential.^[58] These considerations align with broader environmental aspects informed by its moderate persistence and toxicity to water organisms.^[58]

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### Summary of Dimethylethanolamine (Aldrich - 471453)
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Dimethylethanolamine (DMAE) was nominated by the NIEHS for toxicological characterization, including metabolism, reproductive and developmental toxicity, ...
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(1) The additive identified in paragraph (a)(1) of this section is used as a flocculent in the clarification of beet sugar juice and liquor or cane sugar ...
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A clear colorless liquid with a fishlike odor. Flash point 105°F. Less dense than water. Vapors heavier than air. Toxic oxides of nitrogen produced during ...
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Dissociation Constants (pK a ) of Eight Amines: Computations
... Dimethylethanolamine or with N, N-Diethylethanolamine at Temperatures of ... 9.52, 6.85, 9.09, 9.29, 6.66, 8.87, 9.07, 6.48, 8.65, 8.65, 6.14, 8.24. Bis(2 ...
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N,N-Dimethylethanolamine is chemically stable under normal storage conditions, reactive toward acids, and forms salts and esters easily. N,N- ...<|control11|><|separator|>
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Any organic or inorganic acid can be used to adjust pH prior to the distillation step in which the dimethylaminoethanol is recovered as a distillate fraction, ...
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Dimethylethanolamine (DMEA)
Impurities (water, dimethylamine, dimethylamineethoxyethanol, unidentified impurities), % wt max. 0,7. 4, including: – - water, % wt max, 0,2.Missing: purity specifications
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Soluble in water, alcohol, ether, acetone, and benzene. SPECIFICATIONS: -Appearance: Colourless liquid. -Odour: Amine-like. -Purity (by G.C.): 99.0%. -Density ...Missing: impurities | Show results with:impurities
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2 -dimethylaminoethanol lacks functional groups which will hydrolyze under environmental conditions. In addition, the substance is found to be readily ...
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Nothing is retrieved...<|control11|><|separator|>
[56]
Substance Information - ECHA
### Summary of Regulatory Status for 2-Dimethylaminoethanol (CAS: 108-01-0)
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Ethanol, 2-(dimethylamino)- - Substance Details - SRS | US EPA
Dimethylethanolamine, Reviewed. CAMEO Chemicals, 2-Dimethylaminoethanol ... TSCA INV SYN, Ethanol, 2-(dimethylamino)-, Unknown, Approved. Related Substances ...
[58]
[PDF] SAFETY DATA SHEET - Fisher Scientific
Nov 10, 2010 · This chemical is a flammable liquid and vapor, causes severe skin burns and eye damage, may cause respiratory irritation, and is toxic if ...
[59]
https://cdxapps.epa.gov/oms-substance-registry-services/substance-details/24802
[60]
UN/NA 2051 - CAMEO Chemicals - NOAA
UN/NA 2051. 8 - Corrosive 3 - Flammable liquid. CAMEO Chemicals has 1 chemical datasheet with response recommendations for this UN/NA number.Missing: Dimethylethanolamine | Show results with:Dimethylethanolamine
[61]
[PDF] Ethanol, 2-(dimethylamino)-: Human health tier II assessment
Jun 28, 2013 · The chemical has an exposure standard of 7.4 mg/m³ (2 ppm) time weighted average (TWA) and 22 mg/m³ (6 ppm) short-term exposure limit (STEL).