This news item was created by students Jackie Love, Corey Malina, and Andrea Hill as part of their Chemistry 212 Collaborative Group Activities in WS00 under the guidance of Prof. Rainer Glaser.

Glaser's "Chemistry is in the News"
To Accompany Wade Organic Chemistry 4/e.
Chapter 21. Carboxylic Acid Derivatives.


For each of the following questions, please refer to the following article:

PRESCRIPTION-STRENGTH CHOCOLATE
By Janet Raloff (Science News, 1996)

Editorial Comments

Chocolate is probably the world's most craved food. In fact, chocolate cravings have become so well known that people who have them are commonly referred to as "chocoholics." In some countries, chocolate is a major aspect of a yearly diet. A typical Swiss eats over twenty pounds of the sweet stuff per year and Americans down an average of 11.5 pounds of chocolate each year, although some take the cravings too far and, as a result, chocolate has become a major factor in overcoming eating disorders such as anorexia_and_bulemia. Others have come to rely on this most loved confection as a temporary relief for depressions.

So why has the craving for chocolate become so strong? Is it just the sweet creamy flavor that keeps people coming back for another truffle or is there something hidden in chocolate's molecular makeup that contributes to this worldwide passion?

There are a number of researchers that now believe the latter-that there is in fact a molecular reason why people crave chocolate more than other foods. Late in October 1996, while acting on a hunch, Daniele Piomelli and his coworkers isolated a cannbinoid named anandamide and two related chemicals, n-linoeloylethanolamine and n-oleoylethanolamine. Cannabinoids are chemicals related to the molecule THC , or tetrahydrocannabinol, the substance in marijuana responsible for creating its notorious "high." All of these chemicals can work together or independently to "enhance a sense of pleasure and well-being" and scientists know this because they have injected animals with anandamide and have observed the same effect as when they inject an animal with THC.

Not much is known about the role of anandamide in the brain, but scientists have concluded that it does in fact activate the same cellular receptors as THC. It is also known that anandamide's life span once in the brain is quite short, but scientists have found that THC's other chemical cousins present in chocolate, n-oleoylethanolamine and n-linoleoylethanolamine, lengthen anandamide's cerebral effect. Piomelli and his colleagues found that these two unwieldy molecules also have a higher concentration in chocolate than anandamide and that pleasure derived from chocolate is actually due to their prolonging effects.

Now...we know you're thinking..."if chocolate contains all if these THC-like compounds, then why doesn't it produce a high similar to marijuana?" This question is answered by the fact that the n-linoleoylethanolamine, n-oleoylethanolamine, or anandamide do not bind to the same cannabinoid receptors as does THC. You see...if one "smokes a joint", all of the cannabinoid receptors in the brain are activated by THC resulting in a "global high." Whereas chocolate's effect is limited to the amount of anandamide present and its location in the brain producing only prolonged natural effects.

But...when considering chocolate's popularity...most people have already realized these effects.

Pertinent Text References
Chapter 21. Carboxylic Acid Derivatives.



Questions

Question 1: Using ChemFinder, draw the structure of THC.

Question 2: What is a cannabinoid and what are some chemicals that are considered to be cannabinoids?

Answer: Cannabinoids are substances derived from or related to marijuana. Some of cannabinoids include anandamide, n-linoleoylethanolamine, n-oleoylethanolamine, cannabinolic acid, and cannabidiol.

Question 3: In the article it states that scientists know that anandamide produces the same effects as THC in animals. Do you think this is enough evidence to conclude that anandamide will produce the same effects as THC in humans?

Question 4: People already self-prescribe chocolate for depression and it is speculated that the anandamide in the chocolate actually helps them become less depressed. Considering this, do you think that it is possible that in the future scientists will be able to isolate and strengthen anandamide, put it back into the chocolate, and market a prescription strength anti-depressant chocolate bar?

Question 5: "Magic Brownies", or brownies laced with marijuana, are often rumored to have a a longer lasting high( up to 12 hours) than what is produced when just smoking it. With the information presented in the article, devise a reason why this might be so.