Alkanolamine

In organic chemistry, alkanolamines (amino alcohols) are organic compounds that contain both hydroxyl (−OH) and amino (−NH₂, −NHR, and −NR₂) functional groups on an alkane backbone. Most alkanolamines are colorless.^[1]

• Alkanolamines
• Methanolamine, from the reaction of ammonia with formaldehyde
• Ethanolamine
• 2-amino-2-methyl-1-propanol is a precursor to oxazolines
• valinol is derived from the amino acid valine
• Sphingosine is a component of some cell membrane.

1-Aminoalcohols

1-Aminoalcohols are better known as hemiaminals. Methanolamine is the simplest member. 1-Aminoalcohols tend to be labile, readily converting to more highly condensed derivatives or hydrolyzing to the amine and carbonyl.

2-Aminoalcohols

2-Aminoalcohols are an important class of organic compounds that are often generated by the reaction of amines with epoxides:

C₂H₄O + R−NH₂ → RNHC₂H₄OH

Simple alkanolamines are used as solvents, synthetic intermediates, and high-boiling bases.^[1]

Hydrogenation or hydride reduction of amino acids gives the corresponding 2-aminoalcohols. Examples include prolinol (from proline), valinol (from valine), tyrosinol (from tyrosine).

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.

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)

References

External links

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