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 -
Bis(hydroxymethyl)urea is a commercially useful hemiaminal -
An unusual example of an isolable, acyclic hemiaminal: the adduct of ammonia and hexafluoroacetone -
Hemiaminal ether derived from an aldehyde -
Hemiaminal ether derived from a ketone -
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1-Aminoalcohols
1-Aminoalcohols are better known as hemiaminals. Methanolamine is the simplest member.
2-Aminoalcohols
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.[2]
Sphingosine is a naturally occuring 2-aminoethanol.
Preparation
Ethylene oxide and related epoxides add to amines:[2] C2H4O + R−NH2 → RNHC2H4OH<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
- ^ Smith, Michael B.; March, Jerry (2007), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (6th ed.), New York: Wiley-Interscience, ISBN 978-0-471-72091-1
- ^ a b Matthias Frauenkron; Johann-Peter Melder; Günther Ruider; Roland Rossbacher; Hartmut Höke (2002). "Ethanolamines and Propanolamines". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_001. ISBN 3527306730.
External links
- Amino+Alcohols at the U.S. National Library of Medicine Medical Subject Headings (MeSH)
