Bioorganic Chemistry Amines Chapte 16

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

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

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

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

Nomenclature Heterocyclic Amines *

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

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

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

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

Reaction of Amines Amines are BASES! ?

Reaction of Amines Amines are BASES!

Nomenclature Nomenclature

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

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

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

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

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

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

Alkaloid Example Atropine Plants: Dilate pupils of eyes 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

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

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

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