Ethanolamine

Ethanolamine

Names
Preferred IUPAC name 2-Aminoethan-1-ol
Other names 2-Aminoethanol 2-Amino-1-ethanol Ethanolamine (not recommended) Monoethanolamine β-Aminoethanol β-hydroxyethylamine β-Aminoethyl alcohol Glycinol Olamine MEA Ethylolamine 2-Hydroxyethylamine
Identifiers
CAS Number	141-43-5 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:16000 Y
ChEMBL	ChEMBL104943 Y
ChemSpider	13835336 Y
DrugBank	DB03994 Y
ECHA InfoCard	100.004.986
EC Number	205-483-3
KEGG	D05074 Y
PubChem	700
RTECS number	KJ5775000
UNII	5KV86114PT Y
InChI InChI=1S/C2H7NO/c3-1-2-4/h4H,1-3H2 Y Key: HZAXFHJVJLSVMW-UHFFFAOYSA-N Y InChI=1/C2H7NO/c3-1-2-4/h4H,1-3H2 Key: HZAXFHJVJLSVMW-UHFFFAOYAD
SMILES C(CO)N
Properties
Chemical formula	C2H7NO
Molar mass	61.08 g·mol−1
Appearance	Viscous colourless liquid
Odor	unpleasant ammonia-like odour
Density	1.012 g/cm3
Melting point	10.3 °C (50.5 °F; 283.4 K)
Boiling point	170 °C (338 °F; 443 K)
Solubility in water	Miscible
Vapor pressure	64 Pa (20 °C)
Acidity (pKa)	9.50
Refractive index (nD)	1.4539 (20 °C)
Hazards
Safety data sheet	JT Baker
R-phrases	R20, R34, R36/37/38
S-phrases	S26, S27, S36/37, S39, S45
NFPA 704	2 3 0
Flash point	85 °C (185 °F; 358 K) (closed cup)
Autoignition temperature	410 °C (770 °F; 683 K)
Explosive limits	5.5 - 17%
Lethal dose or concentration (LD, LC):
LD50 (median dose)	3320 mg/kg (rat, oral) 620 mg/kg (guinea pig, oral) 2050 mg/kg (rat, oral) 1475 mg/kg (mouse, oral) 1000 mg/kg (rabbit, oral) 700 mg/kg (mouse, oral) 1720-1970 mg/kg (rat, oral)
US health exposure limits (NIOSH):
PEL (Permissible)	TWA 3 ppm (6 mg/m3)
REL (Recommended)	TWA 3 ppm (8 mg/m3) ST 6 ppm (15 mg/m3)
IDLH (Immediate danger)	30 ppm
Related compounds
Related compounds	N-Methylethanolamine diethanolamine triethanolamine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Ethanolamine, also called 2-aminoethanol or monoethanolamine (often abbreviated as ETA or MEA), is an organic chemical compound with the formula HOCH₂CH₂NH₂. The molecule is both a primary amine and a primary alcohol (due to a hydroxyl group). Ethanolamine is a colorless, viscous liquid with an odor reminiscent to that of ammonia. Its derivatives are widespread in nature, e.g., lipids.

The ethanolamines comprise a group of amino alcohols. A class of antihistamines is identified as ethanolamines, which includes carbinoxamine, clemastine, dimenhydrinate, diphenhydramine, and doxylamine.

Monoethanolamine is produced by reacting ethylene oxide with aqueous ammonia; the reaction also produces diethanolamine and triethanolamine. The ratio of the products can be controlled by changing the stoichiometry of the reactants.

Note that this reaction is exothermic and that controls are needed to prevent a runaway reaction.

Ethanolamine is biosynthesized by decarboxylation of serine:

Ethanolamine is the second-most-abundant head group for phospholipids, substances found in biological membranes (particularly those of prokaryotes), e.g., phosphatidylethanolamine. It is also used in messenger molecules such as palmitoylethanolamide, which has an effect on CB1 receptors.