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Analgesia

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Amine

Definition

• Amine molecules have the general formula of R_3-xNH_x where R is a hydrocarbon group and 0 < x < 3. Put another way, amines are derivatives of ammonia, NH₃, in which one or more hydrogen atoms have been replaced by hydrocarbon groups. Specific examples of amines are shown in the next section.

• An amino group refers to an NH₂ sub-unit within a molecule. See additional information below.

Additional Info

Amines are part of the basic building blocks of life, amino acids, and are widely found in Nature. Because of their chemical reactivity, high availability, and ease of handling, they have widespread use in materials that we use every day.

The nitrogen atom in an amine molecule has a lone pair of electrons which makes most amines act as weak bases. Therefore, most amines react readily with acids, and solutions of amines have pH's greater than 7 (alkaline, basic).

Many amines are volatile and have distinctive, nasty, pungent odors; keep reading!

Some amines and types of amines that merit additional discussion are:

1. Ammonia, NH₃

   Ammonia is the simplest possible amine. The molecule has a trigonal pyramidal structure as shown below. The lone pair of electrons points up from the top of this pyramid; if this lone pair were an atom we could call the shape tetrahedral:

   Ammonia has a boiling point of -33 degrees C and is therefore a gas at room temperature. Although ammonia is a weak base, it is corrosive and can cause severe lung damage or death when inhaled in large concentrations. Solutions of ammonia in water are called aqueous ammonia. A solution of 28-29% of ammonia in water is sometimes called ammonium hydroxide and given the chemical formula NH4OH (such molecules do not actually exist, but this is an old chemist's habit that refuses to die). 10% solutions of ammonia in water are used as "smelling salts". Household ammonia solutions are typically more dilute. Mixing household ammonia and chlorine bleach is exceedingly dangerous and produces a toxic and carcinogenic mixture of chloramine, NH2Cl, and hydrazine, N2H4 (not, as many believe, chlorine gas, Cl2).

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2. Primary amines, RNH₂

   Primary amines are derivatives of ammonia in which one hydrogen has been replaced by a hydrocarbon unit. Some common primary amines (and 3 different ways of naming them) are shown here:

   

   Aniline, shown above, is an example of an industrially important aromatic amine.

3. Secondary amines, R₂NH

   Secondary amines are derivatives of ammonia in which two hydrogens have been replaced by hydrocarbon units. These two units can be the same or different:

   

   Secondary amines are usually less reactive than primary amines because the hydrocarbon groups are larger than a hydrogen atom. This extra bulk reduces the ability of an incoming reactant molecule to interact with the nitrogen atom.

4. Tertiary amines, R₃N

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   Tertiary atoms have three hydrocarbon substituents which may be the same or different. Some examples include: Trimethylamine is a gas with a strongly fish-like odor. In fact, together with other amines, trimethylamine is responsible for the smell of rotting fish. To avoid confusion in naming amines, the substituents (groups) that are attached to the nitrogen atom are given the prefixes N and N'. For example, N,N'-dimethylaniline and 2,6-dimethylaniline are tertiary and primary amines, respectively:

   

5. Quaternary ammonium compounds, R₄NX

   Amines can react with acids and other chemical groups to form quaternary ammonium salts. For example, reaction of ammonia, NH3, with hydrogen chloride, HCl, gives the salt, ammonium chloride, NH4Cl which consists of ammonium cations, NH4+, and chlorine anions, Cl-. Another example is tetramethylammonium bromide, shown on the right.

   Because quaternary ammonium salts are ionic species, they are good electrolytes. Such salts are often used in detergents and other cleaning agents. Quaternary amine salts may produce acidic, basic or neutral solutions depending on the nature of the R groups and the anion (negatively charged ion).

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MSDS Relevance

Amines are incompatible with many substances, particularly acids. Read and follow the warnings/instructions on your MSDS.

Many amines are poisonous by inhalation, ingestion or skin absorption. Always use the proper proper personal protective equipment (PPE) mentioned on the MSDS such as gloves, goggles and aprons. Reducing your use of amines in the workplace, or utilizing fume hoods may help reduce hazards.

Many amines are somewhat soluble in water (and most ammonium salts are), so be sure that any aqueous wastes you dispose of down the drain meet the appropriate EPA guidelines.

Further Reading

• Official IUPAC naming rules for primary as well as secondary and tertiary amines courtesy of ACD Labs.
• Powerpoint slides covering amines by E.V. Blackburn at the U of Alberta.
• Chemistry of Amines, part of the Virtual Textbook of Organic Chemistry by William Reusch, Michigan State U.
• The Facts About Amine-Induced Visual Disturbances, Halovision, Blue Haze or Glaucopsia at Air Products.

See also: base, pH.

Additional definitions from Google and Onelook.

Disclaimer: The information contained herein is believed to be true and accurate, however ILPI makes no guarantees concerning the veracity of any statement. Use of any information on this page is at the reader's own risk. ILPI strongly encourages the reader to consult the appropriate local, state and federal agencies concerning the matters discussed herein.