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Bioorganic Chemistry Amines

Bioorganic Chemistry Amines. Chapte 16. Amines. Amine Nomenclature Amines are derivatives of Ammonia, NH 3 Classified as 1 o , 2 o , and 3 o amines. (Count R groups on Nitrogen.). IUPAC Nomenclature. Amines are named by naming the “ R ” groups And adding “ amine ” as a suffix. 3.

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Bioorganic Chemistry Amines

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  1. Bioorganic ChemistryAmines Chapte 16

  2. Amines • Amine Nomenclature • Amines are derivatives of Ammonia, NH3 • Classified as 1o, 2o, and 3o amines (Count R groups on Nitrogen.)

  3. IUPAC Nomenclature Amines are named by naming the “R” groups And adding “amine” as a suffix

  4. 3 Nomenclature • Aromatic amines • Aniline is parent • Substitution on N is named as a“N-alkyl” or “N,N-dialkyl” aniline

  5. 2 Nomenclature • Nomenclature • Use a “N” to locate alkyl groups • More complicated amines are use “amino” to name the N group as a substituent

  6. * * Nomenclature • Heterocyclic Amines

  7. A Little Organic Fun • http://www.youtube.com/watch?v=mAjrnZ-znkY • http://www.youtube.com/watch?v=HPGE_GJkLJA

  8. Physical Properties • Amine Physical Properties • Boiling points slightly lower than alcohols • Hydrogen bonding • occurs with 1o and 2o amines • not possible with 3o amines • Water solubility is similar to same MW alcohols

  9. Physical Properties • Amine Physical Properties • Strong odors • simple amine have an odor similar to ammonia • resemble the odor of raw fish • some diamines have especially bad odors

  10. Reaction of Amines • Amines are BASES! • React with acids and accept a proton (H+) to Form alkyl ammonium salts

  11. Reaction of Amines • Amines are BASES! ?

  12. Reaction of Amines • Amines are BASES!

  13. Nomenclature • Nomenclature

  14. Quaternary Ammonium Salts • Four alkyl groups on N • only with ammonium salts • NOT made by acidifying an amine

  15. So……. Tell me about some Way Cool far out Amines………….. From Yahoo Images

  16. Alkaloids • Nitrogen containing compounds found in roots, bark, leaves, berries, or fruit. • Thousands have been extracted (in containers or by chewing) and used to produce physiological effects in humans and animals • Some are deadly poisons, some cure diseases and some are addictive drugs

  17. Alkaloid Example • Coniine • Simple alkaloid • Very poisonous • Hemlock plant • Socrates (469-399 BC) • Socrates (469-399 BC) was found guilty • of corrupting the minds of the youth • of Athens and sentenced to death • by drinking a mixture containing • poison hemlock. Hemlock From Yahoo Images

  18. Alkaloid Example • Nicotine • Found in smoking, chewing • Stimulant in small doses • Habit forming • Tars, CO, carcinogenspresent in smoke How do you know how much Nicotine is in a smoke? From Yahoo Images

  19. Alkaloid Example • Caffeine • Stimulating action • Found in: • coffee • tea (black, green) • colas • No-Doz • chocolate (theobromine) From Yahoo Images

  20. Alkaloid Example • Atropine • Plants: • henbane • Belladonna- (deadly nightshade) • Dilate pupils of eyes • “used by Cleopatra and Roman Women to Enlarge the pupils to Look more attractive From Yahoo Images

  21. Alkaloid Example • Morphine • Found in Opium Poppy • Simular compounds include Codeine, Heroin, Demerol, Methadone • Valuable pain killer • Troubled drug for abuse From Yahoo Images

  22. Other Alkaloid Example • Quinine • Cinchona bark • Used to treat Malaria • Strychnine • Nux Vomica • rat poison • Reserpine • Indian Snake Root • lowers bp Indian Snake Root from Yahoo Images

  23. Amphetamines • Amphetamines • Synthetic amines • Powerful stimulants CNS • reduce fatigue • raise glucose blood level • control mild depression • reduce hyperactivity in children • appetite depressant

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