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Advanced Level Chemistry: Organic nitrogen compounds in nature and pharmaceutical products

Part 8. The chemistry of organic nitrogen (organonitrogen) compounds

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Part 8.9 Occurrence of organo-nitrogen compounds in nature & pharmaceutical products


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8.3.1 Pharmaceutical products - a few selected examples

8.3.2 Natural products - a few selected examples


8.3.1 Pharmaceutical products - a few selected examples

Drugs

equation reaction between 4-aminophenol and ethanoyl chloride to form 'Paracetamol', N-(4-hyroxyphenyl)ethanamide and hydrogen chloride

The industrial synthesis of the analgesic paracetamol in using ethanoic anhydride.

Paracetamol is an N-substituted amide.


An overlap of natural hormones and synthetic drugs.

A series of molecules, both natural and synthetic, all having a benzene ring and other functional groups are pointed out.

Apart from D, they all have one chiral carbon atom and exhibit R/S isomerism - mirror image optical isomers.

skeletal formula molecular structure amphetamine phenylephrine adrenaline dopamine noradrenaline tyrosine advanced level organic chemistry doc brown

A The amphetamine molecule has a primary amine group.

Amphetamine is a synthetic amine compound that acts as a central nervous system stimulant to combat drowsiness, chronic fatigue syndrome and narcolepsy.

B The phenylephrine molecule has one phenol group, secondary alcohol group and a secondary amine group.

Phenylephrine is a synthetic amine that is used in medicines as a decongestant to treat a stuffy nose and sinus congestion caused by the common cold, hay fever and other allergic conditions.

C The adrenaline molecule has two phenol groups, secondary alcohol group and a secondary amine group.

Adrenaline is naturally produced in the adrenal glands and functions as a hormone, but it is also used as a medication. It is involved in regulating visceral functions like breathing and is involved in the 'fight or flight' response when a animal feels endangered and stressed for some reason e.g. it increases heart rate.

D The dopamine molecule has two phenol groups and a primary amine group.

Dopamine is a type of neurotransmitter. Your body makes it, and your nervous system uses it to send messages between nerve cells. That's why it's sometimes called a chemical messenger. Dopamine plays a role in how we feel pleasure

E The noradrenaline molecule has two phenol groups, secondary alcohol group and a primary amine group.

A chemical released predominantly from the ends of sympathetic nerve fibres and acts to increase the force of skeletal muscle contraction and the rate and force of contraction of the heart.

F The tyrosine molecule has one phenol group, primary amine group and a carboxylic acid group.

L-tyrosine is one of the twenty amino acids that we need to build protein molecules.

It is also an essential component for the production of several important brain chemicals called neurotransmitters, including epinephrine, norepinephrine, and dopamine. Neurotransmitters help nerve cells communicate and influence mood. Tyrosine also helps produce melanin, the pigment responsible for hair and skin color - a very busy molecule!


8.3.2 Natural products - a few selected examples

Other than the obvious amino acids, polypeptides, proteins including enzymes!

Alkaloids

Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom (often a secondary or tertiary amine group).

Alkaloids possess psychotropic, pain-killing, stimulant and toxic properties.

Examples of 'opiates', opium alkaloid molecules like morphine and heroin from plants, long known for their painkilling properties..

Codeine is a safer painkilling analogue of them, but don't overdo it, you can become addicted to codeine tablets!

Strychnine is a deadly alkaloid with rather different effects than those mentioned above!

The stimulants caffeine and nicotine are for many of us our daily does of alkaloid molecules!

Fish oil contain high concentrations of amines, but not simple amines, unlike those very smelly decay products from rotting fish!


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