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

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

6. Nomenclature
Heterocyclic Amines *

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

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 ( BC)
Socrates ( 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, carcinogens present 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: 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

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