Biochemistry 10 GENERAL PRINCIPLES

Prepared and presented by Marc Imhotep Cray, M.D.

Basic Medical Sciences & CK Teacher

Amines and Amides

Reference resources: Organic chemistry-Wikipedia BiochemistryWikipedia Amine Wikipedia Amide - Wikipedia

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Summary

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Classification of Amines. Amines are organic derivatives of ammonia in which one or more of the ammonia hydrogens are replaced by alkyl or aromatic groups. Amines are classified as primary, secondary, or tertiary depending upon the number of groups (one, two, or three) attached to the nitrogen. Nomenclature of Amines. Common names are given to simple amines by adding the ending amine to the names of the alkyl groups attached to the nitrogen. In lUPAC names, the -NH2 group is treated as a chain substituent and given the name amino. Aromatic amines are named as derivatives of aniline. Physical Properties of Amines. Primary and secondary amines have boiling points slightly lower than those of corresponding alcohols. Tertiary amines have boiling points similar to those of alkanes. Low molecular weight amines are soluble in water.

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Chemical Properties of Amines. Amines are weak bases. They react with water to liberate hydroxide ions, and they react with acids to form salts. Amines react with acid chlorides and acid anhydrides to form amides. Biologically Important Amines. Four neurotransmitters are acetycholine, norepinephrine, dopamine, and serotonin. Epinephrine is also known as the "fight or flight" hormone. The amphetamines have structures similar to that of epinephrine. Alkaloids are nitrogen-containing compounds isolated from plants. They exhibit a variety of physiological effects on the body. Examples of alkaloids include nicotine, caffeine, quinine, atropine, morphine, and codeine.
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Amide Nomenclature. Amides are named by changing the -ic acid or -oic acid ending of the carboxylic acid portion of the compound to -amide. Groups attached to the nitrogen of the amide are denoted by a capital N that precedes the name of the attached group. Physical Properties of Amides. Low molecular weight amides are soluble in water due to the formation of hydrogen bonds. Unsubstituted amides have higher melting and boiling points than comparable substituted amides. Chemical Properties of Amides. Amides undergo hydrolysis in acidic conditions to yield a carboxylic acid and an amine salt. Hydrolysis under basic conditions produces a carboxylate salt and an amine.

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Formative Assessment

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An alkaloid used as to suppress a cough is: morphine atropine methadone codeine methadone

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codeine

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When added to water, soluble amines will: alter the solution's color lower solution pH raise solution pH cause water to polymerize

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raise solution pH

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Thank you for your attention

The end

Further Study: Biochemistry and Cell Biology College of Saint Benedict and Saint John's University - Biochemistry Online Indiana University - Medical Biochemistry Page MIT - Biology Hypertextbook NLM - Biochemistry NLM - Molecular Cell Biology University of Utah - NetBiochem

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