Alkanolamine

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.

2-Aminoalcohols

Chemical structure of ethanolamine, a simple amino alcohol

Key members: ethanolamine, dimethylethanolamine, [[N-Methylethanolamine|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.

1-Aminoalcohols

1-Aminoalcohols are better known as hemiaminals. Methanolamine is the simplest member.

1,3-, 1,4-, and 1,5- amino alcohols

• Heptaminol, a cardiac stimulant
• Propanolamines

Natural products

Most proteins and peptides contain both alcohols and amino groups. Two amino acids are alkanolamines, formally speaking: serine and hydroxyproline.

• Veratridine and veratrine
• Tropane alkaloids such as atropine
• hormones and neurotransmitters epinephrine (adrenaline) and norepinephrine (noradrenaline)

2-Amino alcohols from amino acids

In principle, each amino acid can be hydrogenated to the corresponding 2-aminoalcohol. Examples include prolinol (from proline) and valinol (from valine). Some example for EO ethylene oxide and PO propylene oxide reaction that eventually yield aminoalcohol:

C₂H₄O + R−NH₂ → RNHC₂H₄OH

C₃H₆O + R−NH₂ → RNHC₃H₆OH

See also

• Alcohol
• Amine

External links

• Amino+Alcohols at the U.S. National Library of Medicine Medical Subject Headings (MeSH)