February 08, 2006
Wednesday

If, as President Bush said in his State of the Union address, "America is addicted to oil", how come it is LSD that is banned, even for psychiatric research?

According to the Swiss chemist, Albert Hofmann, who invented this mind-altering drug in 1938, it isn't addictive. Like a similarly named, but unrelated, German chemist who had earlier discovered Aspirin by chemically modifying the salicylic acid that is abundant in willow bark, our venturesome chemist was searching for new compounds that might be derived from the lysergic acid that is found naturally in a fungus that grows on wheat.

On the 25th attempt, lysergic acid diethylamide, or LSD-25, was synthesized in good yield. Ultimately, this involves replacing two of the hydrogen atoms that are bonded to the so-called "amide" nitrogen atom, that is on the wagging end of the original molecule, with ethyl groups. Here, "ethyl" has the same meaning as in ethyl alcohol - not your Aunt - and the "di" refers to the fact that this cut-and-splice operation is done twice.

When you translate "acid" to the German word Säure, you repeat what was probably your first experimental observation about the nature of acids (most likely involving citric acid in lemons), and you complete the chemical decoding of the acronym LSD-25.

To understand why LSD was banned in the US, and many other countries, we have to fast-forward to the '60s. It was during this time that the drug became associated with the counter-culture, or "hippie" movement. Nothing wrong with that, but it also earned a hazardous reputation for numerous fatalities that were linked to "bad trips".

Hofmann himself accidentally discovered the hallucinogenic effects of the drug, in April 1943, when he repeated his initial experiment. This time, however, some of the product ended up on his finger, which later ended up in his mouth. Of the ensuing effects, he wrote in his notebook "Everything I saw was distorted, as in a warped mirror". Three days later, he intentionally tested a larger dose, using himself as the guinea pig, but had a far different experience. His neighbor was "transformed into a witch", and he "was filled with an overwhelming fear that (he) would go crazy."

These experiences prompted a flurry of biochemical and psychiatric research, and it was found that LSD was a powerful antagonist of the natural, mood-regulating hormone serotonin. It had also been clinically tested as a treatment for mental disorders. But all that came crashing down in 1966 when the drug was banned.

What does this have to do with our "addiction to oil"? To see things as I see them, you have to take a trip back to the 1800's, when a Swedish chemist named Svante Arrhenius made a daring proposal regarding the chemical classification of acids and bases. His ideas were derived from his doctoral dissertation, which was given a poor rating by his examiners. The thesis concerned the existence of electrically charged "ions" in ordinary water-based solutions. It is a good thing that the examiners didn't have the power to ban his ideas, because he would go on to win the 1903 Nobel Prize in Chemistry. And everything from beer to shampoo would become "pH controlled", which, by the way, is a reference to a chemical measurement that is a flashback to his "theory of electrolytic dissociation".

Arrhenius was also the first to connect the rising levels of atmospheric carbon dioxide levels to a possible "greenhouse effect". This was over 100 years ago, and the levels are rising still. There is no argument over the fact that most of this increase is due to the combustion of hydrocarbons from oil, and from other fossil fuels.

As useful as it was, Arrhenius's theory of acids wasn't the end of the road for acidic daydreams. The American chemist G. N. Lewis envisioned acids that do their thing without ions, and even without water. Indeed, as was found by the British-Canadian chemist Ron Gillespie, water is a real downer when it comes to acid strength. What he termed "superacids" combine the actions of strong acids, such as sulfuric acid, with the drying and boosting effects of solvated Lewis acids. I'll never forget the nasty look of the fuming sulfuric acid in his lab.

Later on, the Hungarian-American chemist George Olah would amplify the acidity of Gillespie's superacids, inventing what he called "magic acid". He did this by replacing one of the oxygen atoms in sulfuric acid with a fluorine atom, and substituting a more potent Lewis acid for the sulfur dioxide that makes sulfuric acid fume.

Magic acid made history when it stabilized a type of ion, called a carbocation, that had long been speculated as a key intermediate in many of the chemical reactions that chemists use to synthesize organic compounds, such as LSD, or to rearrange the structure of simple hydrocarbons to improve combustion efficiency. George Olah won the 1994 Nobel Prize in Chemistry, and, in addition to other important and interesting projects, is searching for ways to synthesize hydrocarbons from water and carbon dioxide, using solar and ambient energy.

If this came to fruition, hydrocarbons could essentially be recycled. It will have been a long, strange trip, and one that started with an idea that was dismissed at first.

Arrhenius and Lewis are long departed, but Gillespie and Olah are still active in research. And Albert Hofmann, who turned 100 on January 11, is still truckin'.

SitNews
Stories In The News
Ketchikan, Alaska