amines & amides dr. michael p. gillespie. introduction amines and amides contain nitrogen....

Amines & Amides

Dr. Michael P. Gillespie

Introduction

• Amines and Amides contain nitrogen.

• Nitrogen is an important component in the structure of the nucleic acids DNA and RNA.

• Amines are characterized by the presence of an amino group (-NH2).

• Histamine contributes to the inflammatory response.

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Introduction

• Amides are the products of a reaction between an amine and a carboxylic acid derivative.

• Amino acids are the subunits from which proteins are built. They are characterized by both an amino group and a carboxyl group.

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Amines: Structure & Properties

• Amines are a family of compounds that are contain an amino group or substituted amino group.

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Amines

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Medically Important Amines

• Amphetamines, such as benzedrine and methedrine, stimulate the central nervous system. They elevate blood pressure and pulse rate and are often used to treat fatigue.

• Medically, they have been used to treat depression and epilepsy.

• Amphetamines decrease the appetite and have been prescribed as diet pills.

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Medically Important Amines

• Many of the medical amines are analgesics (pain relievers) or anesthetics (pain blockers).

• Novacaine is used as a local anesthetic.

• Demerol is a very strong pain reliever.

• Ephedrine is used as a decongestant.

• Sulfa drugs used to fight bacterial infections are made from amines.

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Methamphetamine

• Methamphetamine is an addictive drug known by many names such as “speed”, “crystal”, “crank”, “ice”, and “glass”.

• Ephedrine, which is used as a nasal decongestant, can be used as the starting material for methamphetamine.

• Methamphetamine can be smoked, taken orally, snorted, or injected depending upon the form of the drug.

• It stimulates the release of dopamine and norepinephrine into regions of the brain that control feelings of pleasure.

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Methamphetamine

• Symptoms of long-term abuse include addiction, anxiety, violent behavior, confusion, psychotic symptoms of paranoia, hallucinations, and delusions.

• In severe cases paranoia results in homicidal and / or suicidal feelings.

• Elevated heart rate and blood pressure can lead to strokes.

• In severe cases, cardiovascular collapse and death result.

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Heterocyclic Amines

• Heterocyclic amines are cyclic compounds that have at least one nitrogen atom in the ring structure.

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Amides: Structure & Properties

• Amides are formed in a reaction between a carboxylic acid derivative and an amine.

• The amine bond is the bond between the carbonyl carbon of the acyl group and the nitrogen of the amine.

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Amides

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Medically Important Amides

• Barbiturates (“downers”) are derived from amides and are used as sedatives.

• Acetaminophen is an amide.

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Neurotransmitters

• Neurotransmitters are chemicals that carry signals from a nerve cell to a target cell.

• The signals can be inhibitory or excitatory and they are all nitrogen containing compounds.

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Catecholamines

• The catecholamines include dopamine, norepinephrine, and epinephrine.

• Too little dopamine produces Parkinson’s disease.

• Too much dopamine is associated with schizophrenia.

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Serotonin

• A deficiency of serotonin is associated with depression and eating disorders.

• Serotonin is also involved in pain perception, regulation of body temperature, and sleep.

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Histamine

• Histamine contributes to allergy symptoms.

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γ-Aminobutyric Acid & Glycine

• γ-Aminobutyric Acid (GABA) & Glycine are inhibitory neurotransmitters.

• It is believed that GABA is involved in control of aggressive behaviors.

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Acetylcholine

• Acetylcholine is a neurotransmitter that functions at the neuromuscular junction.

• It carries signals from the nerve to the muscle.

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Nitric Oxide & Glutamate

• Nitric oxide and glutamate function in a positive feedback loop.

• They are thought o be involved in learning and the formation of memories.

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