Alkanolamines are chemical compounds that contain both hydroxyl (-OH) and amino (-NH2, -NHR, and -NR2) functional groups on an alkane backbone. The term alkanolamine is a broad class term that is sometimes used as a subclassification.
1-Aminoalcohols are better known as hemiaminals. Methanolamine is the simplest member.
Key members: ethanolamine, dimethylethanolamine, N-methylethanolamine, Aminomethyl propanol
Two popular drugs, often called alkanolamine beta blockers, are members of this structural class: propranolol, pindolol. Isoetarine is yet another medicinally useful derivative of ethanolamine.
2-Aminoalcohols are an important class of organic compounds that are often generated often by the reaction of amines with epoxides. Simple alkanolamines are used as solvents, synthetic intermediates, and high-boiling bases.
Ethylene oxide and related epoxides add to amines:
- C2H4O + R−NH2 → RNHC2H4OH
Hydrogenation of amino acids gives the corresponding 2-aminoalcohols. Examples include prolinol (from proline) and valinol (from valine).
1,3-, 1,4-, and 1,5-amino alcohols
Most proteins and peptides contain both alcohols and amino groups. Two amino acids are alkanolamines, formally speaking: serine and hydroxyproline.