Chemistry:Alkanolamine

Short description: Organic compounds with hydroxyl and amino groups on an alkane backbone

In organic chemistry, alkanolamines (amino alcohols) are organic compounds that contain both hydroxyl (–OH) and amino (–NH
2, –NHR, and –NR
2) functional groups on an alkane backbone. Most alkanolamines are colorless.

• 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.

2-Aminoalcohols

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

C
2H
4O + R–NH
2 → RNHC
2H
4OH

Simple alkanolamines are used as solvents, synthetic intermediates, and high-boiling bases.

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)

External links

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