Amines By: Cody Rees, Cassie Ritchie, and Courtney Smith

Naming: Naming of amines follows the rule of naming Alkalines, where the alkyl groups are named first followed by “amine”. Ex: Methylamine Butylamine

Naming: Amines are also classified into 3 groups according to the number of carbon atoms attached to the nitrogen. Primary amines have one carbon atom attached to the nitrogen atom, secondary amines have two carbon atoms attached to the nitrogen atom, and tertiary amines have three carbon atoms attached to the nitrogen atom.

General Structure/Formula: Amines are built around a central nitrogen with a lone pair of electrons, and have various types of hydrocarbons, or simply hydrogen, attached to the nitrogen. Each R represents either a hydrogen or a hydrocarbon.

Reaction Properties/Synthesis: Preparing amines by process of alkylation is the most industrially significant way to create them from ammonia. The easiest way to do so is through reductive reactions involving hydrogen. These reactions are made even easier by using nickel as a catalyst. General Formula: ROH + NH 3 → RNH 2 + H 2 O

Physical/Chemical Properties: Amines are only slightly polar, much less so than water Amines are basic The smaller the amine, the more soluble it is Solubility diminishes with an increasing number of carbon Smaller amines have smells similar to ammonia, while larger amines smell of fish and decay

Uses: Medical Many of the amines that are used in drugs are isolated from plants, also known as alkaloids. Some examples include nicotine, coniine, and strychnine. Nicotine may have a pleasant effect when taken in small quantities, but becomes extremely toxic when taken in large quantities. Methylpyrrolidinylpyridine (Nicotine) Structural Formula:

Uses: Medical Many opioide drugs are attached to an amine, which include morphine, codeine, levorphanol, heroin, and demerol. Each of these has a methyl group attached to the nitrogen atom. Methyloxazapentacyclooctadecatetraenediol Structural Formula: Methylmorphinan Structural Formula:

Uses: Medical Diacetylmorphine Structural Formula: Methylmorphine Structural Formula: Ethylmethylphenylpiperidinecarb oxylate (Demerol) Structural Formula:

Uses: Medical The popular painkiller Tylenol, also known as acetaminophen or paracetamol, is an amine. Its molecular name is N acetylparaaminophenol. Structural Formula:

Uses: Medical Histamines are amine chemicals released into the body that act as neurotransmitters. When released in high quantities, they may cause fatal organ failure. The only known method of stopping histamines from completely shutting a person’s organs down is to inject the person with adrenaline; a chemical that counteracts the histamines effects and destroys them. Histamine (imidazolylethanamine) Structural Formula:

Uses: Medical There is, however, a medication used to stop the body from producing more amines that, if left to develop, would continue to antagonize the person’s organs. This chemical is called an antihistamine, or histamine antagonist. Diphenhydramine Hydrochloride (antihistamine) Structural Formula:

Uses: Dyes

Uses: Toxic Products Heterocyclic amines(HCAs) and polycyclic aromatic hydrocarbons (PHAs) are chemicals that have been known to cause cancer in humans and animals alike. They are formed when muscle meat is cooked using high-temperature methods, such as in a frying pan or over an open flame. In some studies, rodents that have been fed a diet that included HCAs developed tumors of the breast, colon, liver, skin, lung, prostate, and other organs. Rodents fed a diet that included PHAs developed several varieties of cancer, including leukemia and malignant tumors of the gastrointestinal tract and lungs.

An example of a heterocyclic amine is Pyridinecarboxylic acid (Niacin). It is theorized that Niacin causes strokes in humans. Structural Formula: Uses: Toxic Products

An example of a polycyclic aromatic hydrocarbon is Benzopyrene. It is present in coal tar like that after a forest fire, in cigarette smoke, and in burnt foods such as coffee. It is considered extremely dangerous and carcinogenic because of its effects on DNA. When in contact with humans, it can intercalate into DNA, interfering with transcription. Structural Formula:

Uses: Toxic Products Coniine is an active ingredient in the poison hemlock, which is also knows as “devil’s porridge”. Instant collapse of the lungs and death are the resultant effects of eating hemlock. Strychnine is used as a pesticide for killing small animals such as mice or squirrels. Strychnidin (Strychnine) Structural Formula: Propylpiperidine (Coniine) Structural Formula: