This news item was created by students Nicole White, Stephanie Heizer, Bonnie Taylor, Troy Fouche, Justin Thomas and Addy Evans 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 20. Carboxylic Acids.


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

PRESIDENT SIGNS TOUGH FEDERAL LAW FOR DATE-RAPE DRUG
by Catherine Strong (Detroit News, 2000)


Editorial Comments

According to the Drug Enforcement Agency, gamma hydroxybutyrate (GHB) has been linked to 58 deaths since 1990. Previously legal in 30 states, including Missouri, a recent Congressional Bill placed GHB on the schedule I controlled substances list. Schedule I drugs include heroin and cocaine and are defined as having a high potential for abuse, having no currently accepted medical use in the United States, and lacking accepted safety measures for use of the drug. The Food and Drug Administration banned GHB in 1991, but a 1994 law made it almost impossible for the federal government to monitor the sales of "diet supplements" containing GBL that metabolize into GHB once ingested. Therefore, the new law also places tighter constraints on GBL, or gamma butyrolactone.

While GHB has been labeled a date rape drug, it is most commonly used intentionally and recreationally. GHB has been promoted commercially as stimulating muscle growth, causing euphoric and hallucinatory states, enhancing sexual performance, and removing paint. GHB is popular at parties and raves as a substitute for alcohol, giving an immediate high with little or no hangover. Despite the fact that the bill was spurred by a death due to its date rape use, most deaths result from intentional users who accidentally overdose.

Current research is seeking possible health benefits of GHB in the treatment of narcolepsy and alcoholism. No conclusive findings have yet been shown by the studies. Currently there are no medical uses of gamma hydroxybutyrate, fulfilling the second requirement for a schedule I controlled substance.

Gamma hydroxybutyrate is a carboxylic acid. Carboxylic acids contain a COOH group and are very soluble in alcohol due to hydrogen bonding. GHB is also colorless and odorless. A few hours after ingestion, GHB metabolizes into CO2 and H20 and no trace remains in the body. These properties make GHB susceptible for use as a date rape drug.

Pertinent Text References
Chapter 20. Carboxylic Acids.
See in particular the discussion of ester saponification in Wade 4/e, p. 973.



Questions

Question 1: Using Chemfinder, find the structure of gamma hydroxybutyrate (GHB) and gamma butyrolactone (GBL).


Question 2: Na-GHB is the sodium salt of GHB, a commonly found form for drug delivery. Show the synthesis of GBL into Na-GHB using Erowid and Chapter 21-7 of Wade.


Question 3: How is GHB used and what are its common side effects?

Answer: This colorless, odorless drug can be found in various forms, including liquid (as used in the MI deaths) or powder. The liquid is most often consumed straight, or mixed with alcohol or soda. The powder can be snorted or injected. While most typically, GHB is expected to enhance sexual performance and simulate alcohol intoxication, users and/or victims may experience the following side effects: drowsiness, nausea, unconsciousness, seizure, severe respiratory depression, coma and death.



Question 4: What is the name of the legislation and how will this new law change federal control of GHB?

Answer: The legislation is called the "Hillory J. Farias and Samantha Reid Date-Rape Drug Prohibition Act of 2000." Currently, GHB falls into a "diet supplement" category that the DEA has no control over. This bill will place GHB in a category of drugs that are strictly regulated by the Federal Controlled Substances Act. Anyone found possessing, manufacturing or distributing GHB may face up to 20 years in prison. The bill additionally gives the DEA power to federally prosecute anyone found possessing or distributing the drug. The bill will place tougher monitoring on GBL distribution and requires the federal government to launch a nationwide public awareness campaign on the dangers of GHB.



Question 5: Knowing that GHB may possibly be used in the treatment of narcolepsy and alcoholism, do those benefits outweigh the enormous risks presented by those using the drug "recreationally" and/or as a date rape drug? How would you vote on the bill and why?