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]

2-Aminoalcohols

Chemical structure of ethanolamine, a simple amino alcohol

2-Aminoalcohols are an important class of organic compounds that contain both an amine and an alcohol functional groups. They are generated often by the reaction of amines with epoxides. Such compounds find a variety of industrial applications. Simple alkanolamines are used as solvents, synthetic intermediates, and high-boiling bases.^[2]

Common amino alcohols

Beta blockers

A subclass of beta blockers is often called alkanolamine beta blockers. Typical examples are:

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 ^[3]^{[circular reference]}

C3H6O + R-NH2 --> RNHC3H6OH^[4]^{[circular reference]}

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
^ "Ethanolamines and Propanolamines". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. 2002. doi:10.1002/14356007.a10_001. {{cite encyclopedia}}: Cite uses deprecated parameter |authors= (help)
^ Ethylene oxide
^ Propylene oxide

External links

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

Template:Amino alcohols

[1] 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

[Ullmann-2] "Ethanolamines and Propanolamines". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. 2002. doi:10.1002/14356007.a10_001. {{cite encyclopedia}}: Cite uses deprecated parameter |authors= (help)

[3] Ethylene oxide

[4] Propylene oxide

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