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Amines

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.

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Amines

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

  2. Naming: Naming of amines follows the rule of naming Alkalines, where the alkyl groups are named first followed by “amine”. Ex: Methylamine Butylamine *It is only possible to name extremely simple amines in this manor*

  3. 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.

  4. 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.

  5. 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 + NH3 → RNH2 + H2O

  6. 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

  7. 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:

  8. 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. Methylmorphinan Structural Formula: Methyloxazapentacyclooctadecatetraenediol Structural Formula: Levorphanol Morphine

  9. Uses: Medical Ethylmethylphenylpiperidinecarboxylate (Demerol) Structural Formula: Diacetylmorphine Structural Formula: Methylmorphine Structural Formula: Heroin Codeine

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

  11. 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:

  12. 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:

  13. Toxic Products Putrescine (diaminobutane) is a foul smelling chemical related to cadaverine that is produced by the breakdown of amino acids in living and dead organisms. It is extremely toxic when taken in large doses, and if found in semen. • Structural Formula:

  14. Toxic Products Cadaverine (pentanediamine) is produced by the breakdown of proteins in tissues of living organisms. Cadaverine produces the distinctive odours of urine and semen, and can help detect complications and defects in lysine metabolism. Structural Formula:

  15. Toxic Products • Skatole (methylindole) is a white crystalline compound produced by tryptophan in the digestive track of mammals. It is toxic, but occurs naturally in feces. Skatole, in low concentrations, produces a flowery smell used in perfumes, and is used as flavouring. It is an additive in cigarettes, and produces pulmonary edema in some mammals. • Structural Formula:

  16. 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.

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

  18. 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:

  19. Toxic Products Strychnine is used as a pesticide for killing small animals such as mice or squirrels. Strychnidin (Strychnine) Structural Formula: 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. Propylpiperidine (Coniine) Structural Formula:

  20. Amines in Forensics • Fluorescein: • Used to detect blood stains at a crime scene • Aids in tracking blood cells during medical health exams • Turns bright purple in water, made useful as a signal during WWII • Nausea, vomiting, hives, cardiac arrest, and sudden death due to anaphylactic shock are results of taking fluorescein topically, orally, or intravenously. • Structural Formula:

  21. Amines in Forensics • Ninhydrin: • Used to detect ammonia, primary amines, and secondary amines • Turns deep purple in color when reacting with other amines • Most commonly used to detect fingerprints • Reacts with amines of lysine residues in peptides and proteins that are rubbed off in fingerprints • Works well on porous surfaces such a paper • Structural Formula:

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