Table of Contents

Cover

Title Page

Dedication

Preface

Acknowledgments

Chapter 1: If You Do Not Know Any Chemistry, This Chapter Is For You

Representing Atoms and Molecules in Chemistry
Neurotransmitters
Intermolecular Forces

Chapter 2: The Only True Aphrodisiac and Other Chemical Extremes

Death Is Its Withdrawal Symptom!
What Is the Number One Cause of Liver Failure in the United States?
The Most Addictive Substance Known
40 Million Times Deadlier Than Cyanide
The Most Abused Drug in the United States
What Is the Only Known Aphrodisiac?
The Most Consumed Psychoactive Substance
40,000 Tons of Aspirin
How Bitter Is the Bitterest?
$62.5 Trillion per Gram
What Is the Most Abundant Source of Air Pollution?
Where Did That Rash Come From?
It Would Take an Elephant on a Pencil
The Largest Industrial Accident in World History
What Is the Most Important Chemical Reaction?
Further Reading
Death is its Withdrawal Symptom!
What is the Number One Cause of Liver Failure in the United States?
The Most Addictive Substance Known
40 Million Times Deadlier Than Cyanide
The Most Abused Drug in the United States
The Only Known Aphrodisiac
The Most Consumed Psychoactive Substance
40,000 Tons of Aspirin
How Bitter is the Bitterest?
$62.5 Trillion per Gram
What is the Most Abundant Source of Air Pollution?
Where Did That Rash Come From?
It Would Take an Elephant on a Pencil
The Largest Industrial Accident in World History
What is the Most Important Chemical Reaction?

Chapter 3: The Poisons in Everyday Things

Why Is Antifreeze Lethal?
Aqua Dots: What a Difference a Carbon Makes!
How Can Visine® Kill You?
Death by BENGAY®
It Is in 93 of People in the United States
The Dreaded…Apricot Pits?
Honey Intoxication
The DMSO Patient
Deadly Helium Balloons
The 2007 Pet Food Recall
Mercury in Vaccines and Eye Drops?
The World's Deadliest Frog
Leaded Candy
Why not Drink “Real” Root Beer?
The Killer Fog
Nail Polish or Nail Poison?
Game Board Danger
What Molecule Killed “Weird Al” Yankovic's Parents?
Deadly Popcorn
Even Water Can Be Poisonous
Further Reading
Why is Antifreeze Lethal?
Aquadots: What a Difference a Carbon Makes!
How can Visine® Kill You?
Death by BENGAY®
It Is in 93% of People in the United States
The Dreaded…Apricot Pits?
Honey Intoxication
The DMSO Patient
Deadly Helium Balloons
The 2007 Pet Food Recall
Mercury in Vaccines and Eye Drops?
The World's Deadliest Frog
Leaded Candy
Why not Drink “Real” Root Beer?
The Killer Fog
Nail Polish or Nail Poison?
Game Board Danger
What Molecule Killed “Weird Al” Yankovic's Parents?
Deadly Popcorn
Even Water can be Poisonous

Chapter 4: Why Old Books Smell Good and Other Mysteries of Everyday Objects

The Smell of Old Books and the Hidden Vanilla Extract Underworld
That Smell Is You!
Electric Blue
The World's Most Abundant Organic Compound
Chalk Used to Be Alive
Decaffeinated? Try Deflavored!
Bad Blood
The Problem with Dry Cleaning
The Smell of Dead Fish
How to Make a Spark
The “New Car Smell”
A Gecko Cannot Stick to It!
Why Are Day Glow Colors and Highlighter Pens So Bright?
Why Your White Clothes Are not Really White?
How Can a Spray-on Sunscreen Be Dangerous?
There Is Ink in That Paper
Vomit and Sunless Tanners
Formaldehyde: Funerals, Flooring, and Outer Space
Further Reading
The Smell of Old Books and the Hidden Vanilla extract Underworld
That Smell is You!
Electric Blue
The World's Most Abundant Organic Compound
Chalk Used to be Alive
Decaffeinated? Try Deflavored!
Bad Blood
The Problem with Dry Cleaning
The Smell of Dead Fish
How to Make a Spark
The “New Car Smell”
A Gecko Can't Stick to it!
Why Are Day Glow Colors and Highlighter Pens So Bright? Why Your White Clothes are not Really White?
How Can Spray-On Sunscreen be Dangerous?
There is Ink in that Paper
Vomit and Sunless Tanners
Formaldehyde: Funerals, Flooring, and Outer Space

Chapter 5: Bath Salts and Other Drugs of Abuse

What Are the Dangers of Bath Salts?
What to Do If You Want Your Skin to Turn Blue
The Flesh-Rotting Street Drug
How Does a Breathalyzer Detect a Blood Alcohol Level?
How to Become a Brewery
How Was a Painkiller Used to Free Hostages?
The Secret Ingredient in Coca-Cola®
Why Is Crack Cocaine So Addicting?
Cocaine Smuggling versus Methamphetamine Manufacture
What Basic Common Ingredient Is Needed to Make the Drugs Vicodin®, Percocet®, Oxycontin®, and Percodan®?
Drug Money Is Right
What Percentage of Americans Use Prescription Drugs?
Are You Ready for Powdered Alcohol?
Ecstasy Is Ruining the Rain Forests
How Are Moldy Bread, Migraine Headaches, LSD, and the Salem Witch Trials All Related?
Further Reading
What are the Dangers of Bath Salts?
What to do If You Want Your Skin to Turn Blue
The Flesh-rotting Street Drug
How does a Breathalyzer Detect a Blood Alcohol Level?
How to Become a Brewery
How was a Painkiller Used to Free Hostages?
The Secret Ingredient in Coca-Cola®
Why is Crack Cocaine so Addicting? Cocaine Smuggling versus Methamphetamine Manufacture
What Basic Common Ingredient is Needed to Make the Drugs Vicodin®, Percocet®, Oxycontin®, & Percodan®?
Drug Money is Right
What Percentage of Americans use Prescription Drugs?
What is Powdered Alcohol?
Ecstasy is Ruining the Rainforests
How are Moldy Bread, Migraine Headaches, LSD, and the Salem Witch Trials all Related?

Chapter 6: Why Oil Is Such a Big Part of Our Lives

What Substance Is Used to Make 80 of All Pharmaceuticals?
Why Do Scientists Think Oil Comes From Fossilized Plants and Animals?
How Is Oil Made?
Where Is Most of the Carbon in the World?
The Most Widely Recycled Material in the United States
What Material Is Used to Make Asphalt?
How Oil Helped to Save the Whales
Further Reading
What Material is used to Make Roughly 80% of all Pharmaceuticals?
Why do Scientists Think Oil Comes from Fossilized Plants and Animals?
How is Oil Made? Where is Most of the Carbon in the World?
The Most Widely Recycled Material in the United States
What Material is used to Make Asphalt?
How Oil Helped to Save the Whales

Chapter 7: Why Junior Mints® Are Shiny and Other Weird Facts about Your Food

Why Is Gum Chewy?
The Problem with Gummi Bears
What Is the Easiest Way to Peel a Tomato?
Another Way to Eat Insect Parts!
Why Is High Fructose Corn Syrup More Consumed than Sugar?
What Causes Rancid Butter to Stink?
Why Does Mint Make Your Mouth Feel “Cold?”
It Is Probably Not Really Fresh Squeezed
Why Are Viruses Added to Some Sandwich Meat?
What Is Margarine Made From?
Why Are Junior Mints® Shiny?
Further Reading
Why is Gum Chewy?
The Problem with Gummi Bears
What is the Easiest Way to Peel a Tomato?
Another Way to Eat Insect Parts!
Why is High Fructose Corn Syrup More Consumed Than Sugar?
What Causes Rancid Butter to Stink?
Why Does Mint Make Your Mouth Feel “Cold?”
It's Probably Not Really Fresh Squeezed
Why are Viruses Added to Some Sandwich Meat?
What is Margarine Made From?
Why are Junior Mints Shiny?

Chapter 8: The Radioactive Banana and Other Examples of Natural Radioactivity

Where Does the Helium We Use in Balloons Come From?
Who Was the First Person to Win Two Nobel Prizes?
Where Is the Radioactive Material in YOUR House?
Which Elements Were First Detected in Radioactive Fallout from a Nuclear Bomb?
Radioactivity in Wristwatches, Exit Signs, and H-Bombs
The Earth Is One Giant Nuclear Reactor
Are Nuclear Reactors “Natural”?
Are Your Gemstones Radioactive?
Radon: The Radioactive Gas in Your Home
The Radioactive Banana
Further Reading
Where Does the Helium We Use in Balloons Come From?
The First Person to Win Two Nobel Prizes
Where is the Radioactive Material in YOUR House?
Which Elements were First Detected in Radioactive Fallout from a Nuclear Bomb?
Radioactivity in Wristwatches, Exit Signs, & H-Bombs
The Earth is One Giant Nuclear Reactor
Are Nuclear Reactors “Natural”?
Are Your Gemstones Radioactive?
Radon: The Radioactive Gas in Your Home
The Radioactive Banana

Chapter 9: Chemistry Is Explosive!

How Do Bullets Work?
What Is the Most Commonly Used Explosive in North America?
What Non-nuclear Substance Is the Most Explosive?
What Poison Is Used as an Explosive in Airbags?
Explosive Heart Medicine
Further Reading
How do Bullets Work?
The is the Most Commonly Used Explosive in North America
What Non-nuclear Substance is the Most Explosive?
What Poison is used as an Explosive in Airbags?
Explosive Heart Medicine

Chapter 10: The Chemistry in Breaking Bad and Other Popular Culture

How Does Methamphetamine Act as a Stimulant?
What Is “Pseudo,” and How Is It Related to Methamphetamine?
What Is Ricin?
The Thalidomide Disaster
What Is Phosphine Gas, and Why Is It a Potential Murder Weapon?
Acetylcholine, Pesticides, and Nerve Gas
Further Reading
How Does Methamphetamine Act as a Stimulant? What is “Pseudo,” and How is it Related to Methamphetamine?
What is Ricin?
The Thalidomide Disaster
What Is Phosphine Gas, and Why Is It a Potential Murder Weapon?
Acetylcholine, Pesticides, and Nerve Gas

Chapter 11: Why You Should Not Use Illegally Made Drugs: The Organic Chemistry Reason

Why You Shouldn't Use Illegally Made Drugs
The Tragic Case of the Frozen Addicts
Further Reading

Index

End User License Agreement

List of Illustrations

Chapter 1: If You Do Not Know Any Chemistry, This Chapter Is For You

Figure 1.1 Look at what hides behind the door of understanding chemistry.
Scheme 1.1 The formation of an ionic bond in NaCl.
Figure 1.2 The structure of some simple molecules.
Figure 1.3 The condensed structure of some simple organic molecules.
Figure 1.4 The condensed structure of the benzene ring.
Figure 1.5 How polymers are represented.
Figure 1.6 Various neurotransmitters.
Figure 1.7 A representation of the lock-and-key model of receptors.
Figure 1.8 Molecules with structures similar to dopamine.
Figure 1.9 A representation of how dopamine and methamphetamine both fit in the dopamine receptor.
Figure 1.10 An example of a dipole intermolecular force.
Figure 1.11 An example of an instantaneous dipole intermolecular force.

Chapter 2: The Only True Aphrodisiac and Other Chemical Extremes

Figure 2.1 The structures of ethanol and GABA.
Figure 2.2 The structure of acetaminophen and its toxic metabolite, NAPQI.
Figure 2.3 Thiol containing compounds that react with NAPQI. The gray box highlights the thiol moiety.
Scheme 2.1 The reaction of NAPQI with the thiol in NAC.
Figure 2.2 The reaction of NAPQI with the thiol in a protein.
Figure 2.4 The structure of nicotine.
Figure 2.5 A comparison of the structures of nicotine and imidacloprid.
Figure 2.6 Apparently cockroaches do not care that nicotine is used as an insecticide.
Figure 2.7 A comparison of testosterone and a generic sterol structure.
Figure 2.8 The structure of caffeine.
Figure 2.9 A treatment for caffeine withdrawal.
Figure 2.10 The structure of aspirin.
Figure 2.11 A comparison of the structures of Denatonium benzoate and lidocaine.
Figure 2.12 A comparison of the structures of glucose and fludeoxyglucose.
Figure 2.13 The true structure of antimatter.
Figure 2.14 The structure of common biogenic volatile organic compounds.
Figure 2.15 The basic structure of graphene.
Figure 2.16 Layering of graphene sheets to form graphite.
Figure 2.17 A representation of graphene's strength.
Figure 2.18 The structure of phosgene.
Scheme 2.3 The reaction of phosgene with a protein.
Figure 2.19 A comparison of the structures of PVC, methylene chloride, and phosgene.
Scheme 2.4 The Haber process.
Figure 2.20 Explosives created using nitric acid.

Chapter 3: The Poisons in Everyday Things

Figure 3.1 A comparison of the structures of ethylene glycol and xylitol.
Scheme 3.1 The conversion of ethylene glycol to glycolic acid.
Figure 3.2 The structure of calcium oxalate.
Scheme 3.2 The conversion of glycolic acid to oxalic acid.
Scheme 3.3 The conversion of ethanol to acetic acid.
Figure 3.3 A comparison of the structures of butanediol and pentanediol.
Scheme 3.4 The conversion of butanediol to GHB.
Figure 3.4 A comparison of the structures of GHB, GABA, and 5-hydroxyvaleric acid.
Figure 3.5 The structure of tetrahydrozoline.
Figure 3.6 A helpful warning.
Figure 3.7 The structures of various salicylates.
Scheme 3.5 The synthesis of polycarbonate using bisphenol A.
Figure 3.8 A comparison of the structures of bisphenol A and estradiol.
Figure 3.9 A comparison of the structures of bisphenol A and bisphenol S.
Scheme 3.6 The decomposition of amygdalin.
Figure 3.10 The structure of laetrile.
Scheme 3.7 The synthesis of imitation benzaldehyde.
Scheme 3.8 The synthesis of methamphetamine using benzaldehyde.
Figure 3.11 The structure of a grayanotoxin.
Figure 3.12 A bear feeling the effects of honey intoxication.
Scheme 3.9 The conversion of DMSO to DMSO_4.
Figure 3.13 The structure of melamine and cyanuric acid.
Figure 3.14 The interaction of melamine and cyanuric acid. The hydrogen bonds are shown as dashed lines.
Figure 3.15 The interaction of cytosine and guanine. The hydrogen bonds are shown as dashed lines.
Figure 3.16 How melamine and cyanuric acid can combine to form a solid that causes kidney damage. The hydrogen bonds are shown as dashed lines.
Figure 3.17 The structure of thiomersal.
Figure 3.18 The structure of batrachotoxin.
Figure 3.19 The structures of safrole and 1′-hydroxysafrole.
Scheme 3.10 The conversion of 1′-hydroxysafrole to a reactive species.
Figure 3.11 The formation of a DNA adduct.
Figure 3.20 The toxic components of nail polish.
Figure 3.21 Nail polish or nail poison?
Figure 3.22 The structure of an urushiol and its quinone form.
Scheme 3.12 The reaction of the quinone form of an urushiol with a protein.
Figure 3.23 The structure of carbon monoxide.
Figure 3.24 The structure of diacetyl.
Figure 3.25 The movement of water during hyponatremia.

Chapter 4: Why Old Books Smell Good and Other Mysteries of Everyday Objects

Scheme 4.1 The synthesis of vanillin from lignin.
Figure 4.1 The structure of some of the molecules that produce the “Old Book” smell.
Scheme 4.2 The formation of “imitation” vanillin from guaiacol.
Figure 4.2 The structure of some of the molecules contained in vanilla extract.
Figure 4.3 The “Old Book” smell.
Figure 4.4 The structure of 1-octen-3-one.
Figure 4.5 A comparison of the structures of cellulose and starch.
Figure 4.6 Some of the molecules responsible for the flavor of coffee.
Figure 4.7 The structure of sugars found on the surface of red blood cells.
Figure 4.9 Another definition of a “universal donor.”
Figure 4.10 A Figure showing that water, ethanol, and sugar all contain –OH groups.
Figure 4.11 How cellulose fibers are held together by hydrogen bonds. The hydrogen bonds are dashed and highlighted in gray.
Figure 4.12 The structure of PERC.
Figure 4.13 The structure of carbon dioxide.
Scheme 4.3 The synthesis of TMA from TMAO.
Scheme 4.4 The synthesis of TMAA from TMA.
Figure 4.14 The structures of benzyl butyl phthalate and PVC.
Figure 4.15 The structure of some of the molecules found in the new car smell.
Figure 4.16 A comparison of the structures of polyethylene and Teflon.
Figure 4.17 Even a gecko cannot stick to a Teflon pan.
Figure 4.18 A representation of the fluorescence process in optical brighteners.
Figure 4.19 The structure of an optical brightener.
Figure 4.20 The structure of bisphenol A.
Scheme 4.5 The formation of the colored form of a leuko dye.
Figure 4.21 A comparison of the structures of DHA and glycerine.
Scheme 4.6 The formation of melanoidin pigments from DHA and proteins.
Figure 4.22 The structure of formaldehyde.
Figure 4.23 The structure of lysine.
Scheme 4.7 The reaction of proteins and formaldehyde.
Scheme 4.8 The reaction of DNA and formaldehyde to form damaged DNA.
Figure 4.24 Formaldehyde: interstellar traveler.

Chapter 5: Bath Salts and Other Drugs of Abuse

Figure 5.1 A comparison of the structures of cathinones and amphetamines.
Figure 5.2 Comparison of the structures of ecstasy and various bath salts.
Figure 5.3 The next generation of mephedrone bath salts.
Figure 5.4 The next generation of MDPV bath salts.
Figure 5.5 The structure of cysteine.
Scheme 5.1 The reaction of an Ag⁺ and a protein.
Figure 5.6 The structure of silver sulfadiazine.
Figure 5.7 A comparison of the structures of krokodil and morphine.
Scheme 5.2 The conversion of codeine to krokodil.
Scheme 5.3 The oxidation ethanol to acetic acid.
Scheme 5.4 The reduction of oxygen to water.
Scheme 5.5 The overall reaction used to measure BAC by a breathalyzer.
Scheme 5.6 The conversion of ethanol to acetic acid.
Figure 5.8 Making the best out of auto-brewery syndrome.
Figure 5.9 Comparison of the structures of fentanyl, carfentanil, and oxycodone.
Figure 5.10 Comparison of cocaine–HCl and cocaine.
Scheme 5.7 The synthesis of crack using baking soda.
Scheme 5.8 The synthesis of methamphetamine from pseudoephedrine.
Figure 5.11 A comparison of the structures of opioids.
Figure 5.12 Molecules that come from the opium poppy.
Figure 5.13 The structure of dextrin.
Figure 5.14 Comparison of molecules which are similar in structure to MDMA.
Scheme 5.9 The conversion of safrole to ecstasy.
Figure 5.15 Comparison of the structures of ergometrine, lysergic acid, and LSD.
Scheme 5.10 The conversion of ergotamine to LSD.
Figure 5.16 A comparison of hallucinogenic molecules that mimic the structure of serotonin.

Chapter 6: Why Oil Is Such a Big Part of Our Lives

Scheme 6.1 The synthesis of Aspirin using Benzene obtained from petroleum.
Figure 6.1 The structure of quinine, aniline, and mauveine.
Figure 6.2 The structure of some basic petrochemicals.
Scheme 6.2 The synthesis of TNT using heptane obtained from petroleum.
Figure 6.3 All of these drugs are made from molecules obtained from petroleum.
Figure 6.4 A comparison of a vanadium containing porphyrin found in crude oil and chlorophyll.
Figure 6.5 The structure of a kerogen fragment. The word “core” represents a connection to a larger molecular matrix.
Figure 6.6 The average molecular structure of molecules found in asphalt.
Figure 6.7 The structure of oleic acid, a fatty acid.
Scheme 6.3 The decomposition of triglycerides to form glycerine and fatty acids.

Chapter 7: Why Junior Mints® Are Shiny and Other Weird Facts about Your Food

Figure 7.1 The structure of isoprene.
Scheme 7.1 The conversion of isopentenyl diphosphate into latex.
Figure 7.2 A comparison of the structures of polymers typically found in gum base.
Figure 7.3 You can thank chemistry for this situation.
Figure 7.4 The structure of glycine and proline.
Figure 7.5 Showing how water becomes imbedded in collagen. Hydrogen bonds are dashed.
Figure 7.6 The structure of carminic acid.
Figure 7.7 The structure of kermesic acid.
Figure 7.8 The structure of sucrose.
Scheme 7.2 The conversion of starch to glucose.
Figure 7.3 The conversion of glucose to fructose.
Figure 7.9 No it does not.
Scheme 7.4 The conversion of a triglyceride into glycerine and fatty acids.
Figure 7.10 The structure of some fatty acids found in butter.
Figure 7.11 A comparison of carboxylic acids that smell bad.
Figure 7.12 The structure of triclosan.
Scheme 7.5 The conversion of leucine into isovaleric acid.
Figure 7.13 The structure of capsaicin and eugenol.
Figure 7.14 A comparison of molecules that activate TRPM8 nerve receptors.
Figure 7.15 The structure of icilin.
Figure 7.16 The structures of ethyl butyrate and limonene.
Figure 7.17 The structure of a typical bacteriophage.
Figure 7.18 Bacteriophages make a great sandwich condiment.
Figure 7.19 A comparison of the packing of saturated and unsaturated chains.
Figure 7.20 A comparison of the structure of a saturated fat and a wax.
Scheme 7.6 The removal of a double bond using hydrogenation.
Figure 7.21 The cis- and trans-configurations of a double bond.
Figure 7.22 The structures of aleuritic acid and shellolic acid.
Figure 7.24 Why they call it confectioner's glaze.

Chapter 8: The Radioactive Banana and Other Examples of Natural Radioactivity

Scheme 8.1 The alpha particle decay of uranium-238.
Scheme 8.2 An alpha particle gaining two electrons to become helium gas.
Figure 8.1 A clown holding balloons filled with radioactive decay (helium).
Scheme 8.3 The alpha particle decay of americium-241.
Scheme 8.4 The absorption of uranium-235 to form uranium-236.
Figure 8.5 The fission of uranium-236.
Scheme 8.6 The formation of einsteinium by neutron bombardment of uranium-238.
Figure 8.7 The formation of fermium by neutron bombardment of uranium-238.
Figure 8.2 Even an atomic bomb can cause chemical reactions.
Scheme 8.8 The beta particle decay of tritium.
Scheme 8.9 The formation of tritium by the neutron bombardment of lithium-6.
Scheme 8.10 The fusion reaction that creates a nuclear explosion.
Scheme 8.11 The alpha particle decay of uranium-238.
Scheme 8.12 The alpha particle decay of radon-222.
Figure 8.3 Even cavemen are concerned about radon.
Scheme 8.13 The beta particle decay of potassium-40.
Figure 8.4 The radioactive banana.

Chapter 9: Chemistry Is Explosive!

Scheme 9.1 The combustion of methane.
Figure 9.1 The structure of a N₂ molecule.
Figure 9.2 The structures of C4, TNT, and nitroglycerin.
Scheme 9.2 The chemical reaction of gun powder.
Figure 9.3 A bullet being pushed to over 1000 mph by the mighty N₂ molecule.
Scheme 9.3 The unbalanced chemical reaction of ANFO.
Figure 9.4 A comparison of the structures of cubane and octanitrocubane.
Figure 9.5 The structure of sodium azide.
Scheme 9.4 The reaction of sodium azide.
Figure 9.6 The structures of potential sodium azide substitutes.
Scheme 9.5 The chemical reaction of nitroglycerin.
Figure 9.7 A comparison of the structures of glycerin, nitroglycerin, and amyl nitrite.
Figure 9.8 An unusual source of nitroglycerin.

Chapter 10: The Chemistry in Breaking Bad and Other Popular Culture

Figure 10.1 A comparison of the structures of dopamine and methamphetamine.
Figure 10.2 A comparison of molecules that are structurally similar to methamphetamine.
Figure 10.3 A comparison of the structures of pseudoephedrine and adrenaline.
Scheme 10.1 The synthesis of methamphetamine from pseudoephedrine.
Figure 10.4 Sadly, a true story.
Scheme 10.2 The synthesis of methamphetamine from phenylacetone.
Figure 10.5 A comparison of the structures of right- and left-handed thalidomides.
Figure 10.6 The structure of phosphine.
Figure 10.7 The structure of acetylcholine.
Figure 10.8 The structure of succinylcholine.
Scheme 10.3 The decomposition of acetylcholine.
Figure 10.9 The structures of some organophosphate insecticides.
Figure 10.10 The structure of phosmet.
Figure 10.11 A comparison of the structures of VX and sarin.
Scheme 10.4 The inactivation of acetylcholinesterase with Sarin gas.
Scheme 10.5 The reactivation of acetylcholinesterase with pralidoxime.

Chapter 11: Why You Should Not Use Illegally Made Drugs: The Organic Chemistry Reason

Figure 11.1 A comparison of the structures of MPPP and meperidine.
Scheme 11.1 The formation of MPTP from MPPP.
Scheme 11.2 The decomposition of meperidine.
Figure 11.2 A comparison of the structures of MPTP and MPP+.
Figure 11.3 A comparison of the structures of dopamine and l-Dopa.

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Title: Strange chemistry : the stories your chemistry teacher wouldn't tell you / by Steven Farmer.

Description: Hoboken, NJ : John Wiley & Sons, 2017. | Includes bibliographical references and index.

Identifiers: LCCN 2017016092 (print) | LCCN 2017026188 (ebook) | ISBN 9781119265290 (pdf) | ISBN 9781119265283 (epub) | ISBN 9781119265269 (pbk.)

Classification: LCC QD37 (ebook) | LCC QD37 .F37 2017 (print) | DDC 540-dc23 LC record available at https://lccn.loc.gov/2017016092

Throughout my whole life whenever I looked, you were there; ready to give me love and support, guidance and security, and praise and encouragement. You filled me with your dreams and showed me what it takes to succeed in life. Without you both none of the things I have accomplished would have been possible. I am truly blessed to have such incredible parents, and I love you both.

Preface

Growing up in Northern California was much more curious than one might think. Napa, being part of Northern California, was affected by the LSD (lysergic acid diethylamine) counterculture centered in Berkeley and San Francisco. LSD was everywhere and I recall multiple instances in high school where a classmate would admit to attending class under the influence of LSD and try to describe the effects. This seems very rebellious, but in one of the most tragic events of my life, a high school friend jumped in front of a car on the highway after ingesting LSD. He was killed instantly. This event had such a profound effect on me that it eventually drove me toward a career in chemistry – I needed to understand what had happened to my friend. How could the ingestion of a molecule cause such profound effects? Is awareness really just a fragile chemical process that can be so easily tricked?

After the mass closures of the 1980s, Napa State Hospital was one of the few remaining state run mental hospitals in California. If you have seen the movie One Flew Over the Cuckoo's Nest, it was filmed at Napa State Hospital. As a child, I would often wonder about the causes of mental illness. I was told that mental illness was the result of a “chemical imbalance” in the brain, but what did that really mean? Could a slight change in a chemical really change our perception of the world?

Similar to many scientists before me, my career in chemistry was driven by a quest to better understand some of the questions that haunted my childhood. Surely, obtaining a degree in chemistry would allow me to understand how hallucinogens work, or what causes mental illnesses. Unfortunately, I was wrong. Chemistry courses seemed to steer clear of any topic of an edgy, dangerous, or unusual nature. In fact, initially learning about these fascinating topics required a course outside the chemistry department. Eventually, a graduate elective course from a psychology department, called “Psychopharmacology,” explained the chemical basis for the effect of hallucinogens and the causes of mental illness (I share what I learned in this book).

Later, when I became a chemistry instructor, I made it a point to share these and other stories. It was delightful to find that almost everyone found these topics just as interesting as I did. As I collected new stories, I realized how much of this material was never discussed as part of the numerous chemistry courses required for my Ph.D. Roughly 90% of these stories contained in this book were learned after I graduated. This is where the subtitle of this book, “The stories your chemistry teacher wouldn't tell you” comes from. It seems that there is an overwhelming push to teach the fundamentals of chemistry while neglecting to show the utility of learning the material by connecting it to the real world. Particularly for organic chemistry, there seems to be an aversion of some of these topics, which I feel is because chemists do not want their science associated with anything that poisons you, blows you up, or gets you high. However, these are the topics that many people find exciting (as can be seen by looking at the plot of almost any action movie). Ask a nonchemist where chemicals appear in everyday life and inevitably the answer involves pharmaceuticals, toxins, or illicit drugs.

To share these stories with my students, I usually would take about 5–10 minutes each week to present one of the stories described in this book. For those of you who are teachers or who plan to be, I can say that these stories have been the largest source of positive feedback I have received from my students. Although there is an enormous amount of material that needs to be covered in a typical chemistry course, I say make the time for these extras. It is that important! On multiple occasions, students admitted to me that they only came to class that day so that they could hear the story. Many times, students would speak to me after the lecture to share how that day's story had touched them in some way. One student had been to the emergency room for an acetaminophen overdose, another had a stepfather who was addicted to opioids, and yet another was prescribed amphetamine to treat their attention deficit hyperactivity disorder (ADHD).

You will note that most of the presented stories are short and involve a question or a defined idea. This is done for two reasons: First, I love presenting these questions to my students and trying to evoke an answer from them. Putting students on the spot drives home how little they actually know about the world and how learning chemistry helps them understand their lives. I admit, few things have made me feel more educated than seeing a single simple question stump a classroom with over 400 students. Try it. You will find that very few people know the answers to the questions posed in this book. In addition, some of the cheeky answers I receive have become the highlights of my teaching. Second, I present the stories in a simple format because they will be easy to remember. Jokingly, I tell students to share these stories with their friends and family members so that they can prove that they are receiving an education at Sonoma State University. I am pleased to say that they do just that. An informal poll of my students showed that 90% of them had shared a story at least once, and 75% said that they shared these stories on a regular basis.

Students, like all human beings, want to understand the world around them – they may just not realize it. Telling stories that help students understand and connect to the world they see inspires them in a primal way, making them want to learn and keep coming back for more. This book contains the best stories I have collected over the last 10 years. If you are a teacher, try some of them out and see the profound effect they have on students. Even if you are not a teacher, read on, better understand the world around you, and see how truly strange chemistry can be.

Acknowledgments

To my loving wife, Joy: You are still the most beautiful woman I have ever seen. You are my muse, my life, and the air that I breathe. You are the personification of everything that makes me happy in this world. It was only your love that allowed me to face the adversity I have seen. You have been with me since the start of this journey and I cannot wait to see where life takes us.

To my brother, Richard: Thanks for being the oldest friend I have and for being the funniest person I know.

To my first college chemistry professor, Dr Steven Fawl: Thanks for all of those long talks in your office. Thanks for taking time out for someone who had absolutely no idea what he was going to do with his life. Of all my science professors, you seemed the most worldly and grounded. Your knowledge of chemistry seemed to let you understand the world and how it works. It was because of you that I decided to become a chemist.

To the students of Sonoma State University: Thanks for listening to all of my crazy stories and for continually reminding me why I love teaching so much.

To my colleagues in the chemistry department: Thanks for your help in vetting these stories.

To my agent, Priya Doraswamy of Lotus Lane Literary (lotuslit.com): Thanks for being one of the nicest people I have ever worked with and for helping me realize my dream.

To my editor, Christine Miller (http://tellmewhatyouwanttosay.com): Thanks for all of your encouragement and for helping me find my voice.

To Michelle Sanner: Thanks for your help with the acetaminophen story and helping to start me down the chemical education path.

Strange Chemistry

The Stories Your Chemistry Teacher Wouldn't Tell You

Dedication

Preface

Acknowledgments