- Related Topics:
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- Chemistry LibreTexts - Amines and Heterocycles (Oct. 16, 2026)
amine
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What is an amine?
An amine is a nitrogen-containing organic compound derived from ammonia (NH3). Amines are classified as primary, secondary, or tertiary, depending on how many hydrogen atoms in ammonia have been replaced by organic groups.
They can be aliphatic, with only aliphatic groups attached, or aromatic, with one or more aryl groups attached. Amines can be open-chain or cyclic, where the nitrogen is part of a ring.
Industrially, amines are used in the production of synthetic resins and fibers, dyes, and pharmaceuticals. They are also utilized as corrosion inhibitors, antioxidants, and developers in photography. Amines are found in living tissue and are produced synthetically.
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How are amines different from other chemical compounds?
Amines are a family of nitrogen-containing organic compounds derived from ammonia (NH3). They are classified as primary (RNH2), secondary (R2NH), or tertiary (R3N), depending on how many hydrogen atoms in ammonia are replaced by organic groups.
Other differences:
* Molecular Shape An amine molecule has a somewhat flattened triangular pyramid shape, with the nitrogen atom at the apex.
* Basicity Aliphatic amines are stronger bases than ammonia, while aromatic amines are weaker.
* Occurrence Amines occur naturally from the putrefaction of protein material, and are present in living tissue. Large quantities of aliphatic amines are made synthetically.
* Uses Amines have many direct uses, such as corrosion inhibitors, antioxidants, and developers in photography. They are also required as part of the syntheses of other products.Created from Britannica articles using AI. AI can make mistakes, so verify using Britannica articles. -
What are the main types of amines?
Amines are organic compounds derived from ammonia (NH3). They are classified based on the number of hydrogen atoms in ammonia that have been replaced by organic groups.
The main types of amines are:
* Primary Amines Represented as RNH2, where one hydrogen atom of ammonia is replaced by an organic group.
* Secondary Amines Represented as R2NH, where two hydrogen atoms are replaced by organic groups.
* Tertiary Amines Represented as R3N, where three hydrogen atoms are replaced by organic groups.
* Quaternary Ammonium Compounds Represented as R4N+X−, these are obtained by replacing all four hydrogen atoms of the ammonium ion (NH4+), and they are associated with an anion.Amines can also be classified as aliphatic (having only aliphatic groups attached) or aromatic (having one or more aryl groups attached). Additionally, they can be open-chain or cyclic, where the nitrogen is part of a ring.
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How are amines commonly formed in nature?
Amines, nitrogen-containing organic compounds derived from ammonia (NH3), form naturally through various processes.
Aliphatic amines arise from protein putrefaction and are found in living tissues like histamine. Methylamines exist in some plants, while polyfunctional amines manifest as alkaloids in plants such as nicotine and morphine.
Nitrogen fixation by microorganisms converts nitrogen to ammonia, nitrites, and nitrates. Symbiotic bacteria like Rhizobium in legumes convert free nitrogen to ammonia within root nodules, which the host plant uses for its development.
During the decomposition of living matter, microorganisms facilitate ammonification, yielding ammonia (NH3) and ammonium (NH4+).
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What are some important uses of amines in everyday life?
Amines have several important uses in everyday life. They can act as corrosion inhibitors in boilers and lubricating oils and as antioxidants for rubber and roofing asphalt. Amines are also useful as stabilizers for cellulose nitrate explosives and protectants against damage from gamma radiation.
Additionally, amines are used as developers in photography, flotation agents in mining, anticling and waterproofing agents for textiles, and fabric softeners. Some polyfunctional amines are valuable pharmaceuticals, such as ephedrine and epinephrine (adrenaline), and anesthetics, such as novocaine. Amines are also critical in synthesizing many products, including analgesics, antihistamines, insect repellents, synthetic fibers, and dyes.
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How do amines affect living organisms or the environment?
Amines, nitrogen-containing organic compounds derived from ammonia (NH3), play significant roles in living organisms and the environment.
Environmental Impact
- Nitrogen Cycle Amines are essential to the nitrogen cycle, where microorganisms convert nitrogen into usable forms for plants and animals.
- Pollution Amines can be corrosive to some metals and plastics and should be stored in glass or steel containers. They can also burn in the air, producing carbon dioxide, water, and nitrogen oxides.
Effects on Living Organisms
- Natural Occurrence Amines like alkaloids, catecholamine neurotransmitters, and histamine occur naturally in plants and animal tissues.
- Toxicity While many aliphatic amines are harmless, smaller amines in high concentrations can irritate the skin and mucous membranes. Aromatic amines, like aniline, can be poisonous, damaging blood hemoglobin and potentially causing cancer with prolonged exposure.
- Uses Amines are used as pharmaceuticals, such as ephedrine and epinephrine, and anesthetics, such as novocaine.
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amine, any member of a family of nitrogen-containing organic compounds that is derived, either in principle or in practice, from ammonia (NH3).
Naturally occurring amines include the alkaloids, which are present in certain plants; the catecholamine neurotransmitters (i.e., dopamine, epinephrine, and norepinephrine); and a local chemical mediator, histamine, that occurs in most animal tissues.
Aniline, ethanolamines, and several other amines are major industrial commodities used in making rubber, dyes, pharmaceuticals, and synthetic resins and fibres and for a host of other applications. Most of the numerous methods for the preparation of amines may be broadly divided into two groups: (1) chemical reduction (replacement of oxygen with hydrogen atoms in the molecule) of members of several other classes of organic nitrogen compounds and (2) reactions of ammonia or amines with organic compounds.
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Amines are classified as primary, secondary, or tertiary depending on whether one, two, or three of the hydrogen atoms of ammonia have been replaced by organic groups. In chemical notation these three classes are represented as RNH2, R2NH, and R3N, respectively. A fourth category consists of quaternary ammonium compounds, which are obtained by replacement of all four hydrogen atoms of the ammonium ion, NH4+; an anion is necessarily associated (R4N+X−). Amines are also classified as aliphatic, having only aliphatic groups attached, or aromatic, having one or more aryl groups attached. They may be open-chain, in which the nitrogen is not part of a ring, or cyclic, in which it is a member of a ring (generally aliphatic).
Nomenclature of amines
The older and most widely used system for naming amines is to identify each group that is attached to the nitrogen atom and then add the ending -amine, as in methylamine, CH3NH2; N-ethyl-N-propylamine (or ethyl(propyl)amine), CH3CH2NHCH2CH2CH3; and tributylamine, (CH3CH2CH2CH2)3N. Two or more groups cited are in alphabetical order; to clarify which groups are attached to nitrogen rather than to each other, Ns or internal parentheses are used. A few aromatic amines and most cyclic amines have trivial (nonsystematic) names (e.g., aniline, C6H5NH2), which may be used as a parent (basic structural unit) on which to specify any other groups attached, as in N,N-dimethylaniline.
An alternative method replaces the terminal -e of a hydrocarbon name by the suffix -amine to indicate the functional group ―NH2. With secondary and tertiary amines, the largest group is chosen as the parent, and the other groups are named as substituents. The names in this system for the previous examples are methanamine, N-ethylpropanamine, and N,N-dibutylbutanamine. Dimethylaniline is named N,N-dimethylbenzenamine. When another functional group of the compound has a higher priority than the amino group (―NH2, ―NHR, or ―NR2), the latter is named as a substituent, as in aminoacetic acid, NH2―CH2COOH, and 2-(dimethylamino)ethanol, (CH3)2N―CH2CH2OH. (The simple guidelines given here may not be adequate for more-complex structures.)
Properties of amines
Physical properties
Distinctive odours that are fishy to putrid characterize the lower-molecular-weight amines. They are gases at room temperature or are easily vaporized liquids. Aliphatic amines are less dense than water, having densities in the range 0.63 to 0.74 gram per cubic cm; aromatic amines are typically slightly heavier than water (e.g., the density of aniline is 1.02 grams per cubic cm). With increasing size, they become less volatile; the odour decreases and eventually becomes unnoticeable, although some diamines have offensive odours. For example, H2N(CH2)4NH2, called putrescine, and H2N(CH2)5NH2, called cadaverine, are foul-smelling compounds found in decaying flesh. Amines are colourless; aliphatic amines are transparent to ultraviolet light, but aromatic amines display strong absorption of certain wavelengths. Amines with fewer than six carbons mix with water in all proportions. The aliphatic amines are stronger bases than ammonia, and the aromatic ones are substantially weaker. The basicity is measured in terms of the pKb value, which is equal to −logKb, where Kb is the equilibrium constant for the reaction B + H3O+ ⇌ BH+ + H2O (B is the amine). Thus, a larger pKb value indicates greater strength as a base. For comparison, the pKb of ammonia is 4.75. Quaternary ammonium hydroxides are very strong bases, but the chlorides are not basic.
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| substituent group, R | RNH2 | R2NH | R3N | |||
|---|---|---|---|---|---|---|
| boiling point (°C) | pKb | boiling point (°C) | pKb | boiling point (°C) | pKb | |
| *Melting point −6.24 °C. | ||||||
| **Melting point 52.8 °C. | ||||||
| ***Melting point 127 °C. | ||||||
| CH3 | −6 | 3.38 | 7 | 3.36 | 3.5 | 4.24 |
| C2H5 | 16.5 | 3.37 | 55.5 | 3.02 | 89.4 | 3.35 |
| n-C4H9 | 77.8 | 3.41 | 161 | 2.75 | 214 | 3.11 |
| sec-C4H9 | 66 | 3.44 | 132 | 2.99 | ||
| tert-C4H9 | 45 | 3.55 | 95 | |||
| C6H5 | 184.4* | 4.59 | 302** | 0.85 | 365*** | <0 |
Most aliphatic amines are not highly toxic, and many are harmless, natural components of foods and pharmaceuticals. In high concentrations, however, the smaller amines are highly irritating to the skin and especially to the mucous membranes of the eyes, nose, throat, and lungs, to which they can cause acute damage upon prolonged exposure. Larger amines (12 or more carbon atoms) are usually less irritating. Aromatic amines are also irritants and can be absorbed through the skin. They may be dangerous poisons. Aniline, for example, destroys the hemoglobin of blood, and prolonged exposure has been linked with cancer. Amines can be corrosive to some metals and plastics; they should therefore be stored in glass or steel containers.
Molecular shape and configuration
An amine molecule has the shape of a somewhat flattened triangular pyramid, with the nitrogen atom at the apex. An unshared electron pair is localized above the nitrogen atom. In quaternary ammonium ions this region is occupied by a substituent, forming a nearly regular tetrahedron with the nitrogen atom at its centre.
Left-handed and right-handed forms (mirror-image configurations, known as optical isomers or enantiomers) are possible when all the substituents on the central nitrogen atom are different (i.e., the nitrogen is chiral). With amines, there is extremely rapid inversion in which the two configurations are interconverted. The process is like an umbrella turning inside out in the wind; the substituents move in one direction (“up”) and the nitrogen atom in the other (“down”). Quaternary ammonium ions do not undergo such equilibration short of conditions where they decompose; their optical isomers are indefinitely stable and isolable, and the physiological effects of the two enantiomers may be profoundly different.