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.^[1]

• Alkanolamines
• 

  methanolamine, an intermediate in the reaction of ammonia with formaldehyde

• 

  [[Ethanolamine] is a commercially useful

• 

  2-amino-2-methyl-1-propanol is a precursor to oxazolines

• 

  valinol is derived from the amino acid valine

• 

  Sphingosine is a component of somee cell membrane.

1-Aminoalcohols[]

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

2-Aminoalcohols[]

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.^[2]

Preparation[]

Ethylene oxide and related epoxides add to amines:^[2]

C
2H
4O + R−NH
2 → RNHC
2H
4OH<ref>

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[]

• 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 US National Library of Medicine Medical Subject Headings (MeSH)