Heterocylic amines

Page 1: Introduction to Heterocyclic Amines

• Definition: A heterocyclic amine is a cyclic organic compound that contains a ring of five or six atoms, with one or two of those atoms being nitrogen.

• Example: The aroma of black pepper is attributed to the presence of piperidine, which is a type of heterocyclic amine.

Page 2: Heterocyclic Amines - Five-Atom Rings

• Types of Five-Atom Rings:

  • Pyrrolidine:

    • Structure: Contains four carbon atoms and one nitrogen atom.

    • Bonds: All single bonds.

  • Pyrrole:

    • Structure: A five-atom ring that includes one nitrogen atom and two double bonds.

  • Imidazole:

    • Contains two nitrogen atoms within the five-atom structure.

Page 3: Heterocyclic Amines - Six-Atom Rings

• Types of Six-Atom Rings:

  • Piperidine:

    • Responsible for the pungent aroma and taste associated with black pepper.

    • Composed of six atoms including one nitrogen atom.

  • Purine and Pyrimidine:

    • Essential components found in DNA and RNA.

    • Structure: Purine comprises a combination of a six-atom pyrimidine and a five-atom imidazole ring.

Page 4: Alkaloids - Amines in Plants

• Definition of Alkaloids: Physiologically active compounds produced by plants containing heterocyclic amines.

• Applications:

  • Used in anesthetics, antidepressants, and stimulants.

  • Many alkaloids are habit-forming.

  • Nicotine:

    • An alkaloid stimulant that increases adrenaline levels, heart rate, and blood pressure.

    • Addictive due to its activation of pleasure centers in the brain.

Page 5: Caffeine - Another Important Alkaloid

• Source: Found in coffee beans, tea, chocolate, and soft drinks.

• Effects:

  • Central nervous system stimulant.

  • Increases alertness but may lead to insomnia.

Page 6: Other Alkaloids - Morphine and Codeine

• Morphine and Codeine:

  • Obtained from the oriental poppy plant.

  • Commonly used as painkillers and included in cough syrups.

Page 7: Heroin and OxyContin - Modified Alkaloids

• Heroin:

  • Derived from a chemical modification of morphine.

  • Not used medically due to its strong addictive qualities.

• OxyContin (oxycodone):

  • Prescription drug used for severe pain relief.

  • Chemical structure is similar to that of heroin.

Page 8: Learning Check on Heterocyclic Amines

• Activity: Identify the heterocyclic amines from a provided list labeled A, B, C, and D.

Page 9: Solution to Learning Check

• Identification Results:

  • A, B, and C qualify as heterocyclic amines, while D does not.