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2-Dimethylaminoethanol

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2-Dimethylaminoethanol Basic information

Product Name:
2-Dimethylaminoethanol
CAS:
108-01-0
MF:
C4H11NO
MW:
89.14
EINECS:
203-542-8
Mol File:
108-01-0.mol
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2-Dimethylaminoethanol Chemical Properties

Melting point:
−70 °C(lit.)
Boiling point:
134-136 °C(lit.)
Density 
0.886 g/mL at 20 °C(lit.)
vapor pressure 
100 mm Hg ( 55 °C)
refractive index 
n20/D 1.4294(lit.)
Flash point:
105 °F
storage temp. 
Flammables area
solubility 
alcohol: miscible(lit.)
form 
Liquid
pka
pK1:9.26(+1) (25°C)
color 
Clear colorless to pale yellow
PH
10.5-11 (100g/l, H2O, 20℃)
explosive limit
1.4-12.2%(V)
Water Solubility 
miscible
FreezingPoint 
-59.0℃
Sensitive 
Hygroscopic
Merck 
14,2843
BRN 
1209235
Stability:
Stable. Flammable. Incompatible with oxidizing agents, copper, copper alloys, zinc, acids, galvanised iron. Hygroscopic.
InChIKey
UEEJHVSXFDXPFK-UHFFFAOYSA-N
CAS DataBase Reference
108-01-0(CAS DataBase Reference)
NIST Chemistry Reference
Ethanol, 2-(dimethylamino)-(108-01-0)
EPA Substance Registry System
Dimethylaminoethanol (108-01-0)
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Safety Information

Hazard Codes 
C
Risk Statements 
10-20/21/22-34
Safety Statements 
25-26-36/37/39-45
RIDADR 
UN 2051 8/PG 2
WGK Germany 
1
RTECS 
KK6125000
Autoignition Temperature
245 °C
TSCA 
Yes
HazardClass 
8
PackingGroup 
II
HS Code 
29221980
Hazardous Substances Data
108-01-0(Hazardous Substances Data)
Toxicity
LD50 orally in Rabbit: 2130 mg/kg LD50 dermal Rabbit 1220 mg/kg

MSDS

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2-Dimethylaminoethanol Usage And Synthesis

Chemical Properties

Colourless liquid

Uses

dimethyl MEA (DMAE) is also known as dimethylaminoethanol. Studies indicate skin-firming properties, and an ability to reduce the appearance of fine lines and wrinkles as well as dark circles under the eyes. It is considered anti-aging, and antiinflammatory, and has exhibited free-radical scavenging activity.

Production Methods

Synthesis of dimethylaminoethanol can be accomplished from equimolar amounts of ethylene oxide and dimethylamine (HSDB 1988).

Definition

ChEBI: A tertiary amine that is ethanolamine having two N-methyl substituents.

General Description

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 combustion. Used to make other chemicals.

Air & Water Reactions

Flammable. Partially soluble in water and less dense than water.

Reactivity Profile

DIMETHYLAMINOETHANOL is an aminoalcohol. 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. N,N-Dimethylethanolamine may react vigorously with oxidizing materials.

Health Hazard

Inhalation of the vapor or mist can cause irritation to the upper respiratory tract. Asthmatic symptoms have been reported. Extremely irritating; may cause permanent eye injury. Corrosive; will cause severe skin damage with burns and blistering. Ingestion may cause damage to the mucous membranes and gastrointestinal tract.

Health Hazard

Dimethylaminoethanol is classified as a mild skin irritant and a severe eye irritant (HSDB 1988). Doses as high as 1200 mg daily produce no serious side effects and a single dose of 2500 mg taken in a suicide attempt had no adverse effects (Gosselin et al 1976). Reported side effects for the acetamidobenzoate salt of dimethylaminoethanol include occipital headache, constipation, muscle tenseness, restlessness, increased irritability, insomnia, pruritus, skin rash, postural hypotension, and weight loss (HSDB 1988). Under laboratory conditions, asthmatic responses resulted after exposure to a 2% dimethylaminoethanol solution to a spray painter who earlier was exposed to a similar concentration of dimethylaminoethanol via a particular paint (Vallieres et al 1977). Serious cholinergic side effects were reported in a 37 yr-old woman with tardive dyskinesia who had been taking dimethylaminoethanol (Nesse and Carroll 1976). After chronic treatment (5 months) with dimethylaminoethanol, marked sialism, bronchospasm, and parkinson rigidity was observed in an 89 yr-old male with a 50 yr history of chronic paranoid schizophrenia and symptoms of tardive dyskinesia (Mathew et al 1976). Dimethylaminoethanol appears to have a relatively low order of toxicity (HSDB 1988). Upon chronic administration in humans, plasma choline concentrations were found to be increased (Ceder et al 1978). No reports were found in the literature regarding carcinogenic or mutagenic potential.

Industrial uses

Dimethylaminoethanol is used as a chemical intermediate for antihistamines and local anesthetics; as a catalyst for curing epoxy resins and polyurethanes; and as a pH control agent for boiler water treatment. However, dimethylaminoethanol in the salt form, (i.e. dimethylaminoethanol acetamidobenzoate) is primarily utilized therapeutically as an antidepressant (HSDB 1988).

Safety Profile

Moderately toxic by ingestion, inhalation, skin contact, intraperitoneal, and subcutaneous routes. A skin and severe eye irritant. Used medically as a central nervous system stimulant. Flammable liquid when exposed to heat or flame; can react vigorously with oxidzing materials. Ignites spontaneously in contact with cellulose nitrate of high surface area. To fight fire, use alcohol foam, foam, CO2, dry chemical. When heated to decomposition it emits toxic fumes of NOx

Metabolism

When administered orally, dimethylaminoethanol acetamidobenzoate (the therapeutic salt formulation) has been shown to cross the blood-brain barrier (HSDB 1988). Two other studies have examined the pharmacokinetics of dimethylaminoethanol in rats (Dormand et al 1975) and healthy adults (Bismut et al 1986).
It has been postulated that dimethylaminoethanol undergoes endogenous methylation (LaDu et al 1971). After intravenous treatment of mice with [14C]-labeled dimethylaminoethanol in the brain, dimethylaminoethanol yielded phosphoryldimethylaminoethanol and phosphatidyldimethylaminoethanol. Acid-soluble and lipid cholines derived from dimethylaminoethanol also were found in brain (Miyazaki et al 1976). While examining the pharmacokinetics of the maleate acid of [14C]-dimethylaminoethanol in rats, Dormand et al (1975) observed that dimethylaminoethanol was metabolized in the phospholipid cycle and produced metabolites such as phosphoryldimethylaminoethanolamine, and glycerophosphatidylcholine. In kainic-acid lesioned rats, dimethylaminoethanol was converted to a substance which cross-reacted in the radioenzymatic assay for acetylcholine (London et al 1978). Ansell and Spanner (1979) demonstrated that [14C]-dimethylaminoethanol rapidly disappeared from brain; after 0.5, 1, and 7 h, only 30, 27, and 16% of the administered radioactivity, respectively, remained in the brain after intracerebral injection. They also showed that brain levels of phosphodimethylaminoethanol increased to a maximum at 1-2 h and decreased afterwards, whereas concentrations of phosphatidylethanolamine increased continuously throughout the 7 h observation period. This study further found that after i.p. injections of labeled dimethylaminoethanol, the brain content of phosphatidylethanolamine increased through the 7 h period and the levels were 10-40 fold higher than those of phosphodimethylaminoethanol.

Purification Methods

Dry the amine with anhydrous K2CO3 or KOH, and fractionally distil it. [Beilstein 4 IV 1424.]

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