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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 Ethylmethylamine . General Structure/Formula:.

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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 Ethylmethylamine

  3. General Structure/Formula: Amines are built around a central nitrogen with a lone pair of electrons, and have hydrocarbons of various types attached to the nitrogen.

  4. Reaction Properties/Synthesis: The easiest way to form amines is through reductive reactions involving hydrogen. These reactions are made even easier by using nickel as a catalyst.

  5. Reaction Properties/Synthesis: Preparing amines by process of alkalisation with alcohols is the most industrial significant way to create them from ammonia. ROH + NH3 → RNH2 + H2O These reactions require catalysts, specialized apparatus, and additional purification measures since the selectivity can be problematic. The same amines can be prepared by treatment of Haloalkanes with ammonia and amines: RX + 2 R'NH2 → RR'NH + [RR'NH2]XSuch reactions, which are most useful for alkyl iodides and bromides, are rarely employed because the degree of alkylation is difficult to control

  6. 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:

  7. 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:

  8. Uses: Medical Ethylmethylphenylpiperidinecarboxylate (Demerol) Structural Formula: Diacetylmorphine Structural Formula: Methylmorphine Structural Formula:

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

  10. Uses: Medical Histamines are amine chemicals released into the body that act as neurotransmitters. When released in high quantities, they may cause severe organ failure. The only known method of stopping histamines from completely shutting a person’s organs down is to inject them with adrenaline; a chemical that counteracts the histamines effects and destroys them. There is, however, a medication used to stop more amines from being produced to further antagonize the person’s organs.

  11. 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.

  12. Uses: Dyes

  13. 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.

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

  15. 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:

  16. Uses: 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:

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