This news item was created by students Christian Balzer, Rohit Parihar, Brian Quigly, and Brian McVey as part of their Chemistry 216 Collaborative Group Activities in FS01 under the guidance of Prof. Rainer Glaser.

Glaser's "Chemistry is in the News"

By Scott Martelle, Los Angeles Times, November 5, 2001.

Editorial Comments

The US government is currently detaining four terrorists supposedly linked with Osama Bin LadenÕs Al Qaeda terrorist network. The terrorists are thought to have information that the FBI has been unsuccessful at extracting with government approved methods of coercion. This has led to a consideration of possible alternatives, one of which is the use of sodium pentothal, the best known truth serum. Sodium Pentothal is a barbituate, a substance which helps channels in the neurotransmitters stay open longer and when gamma aminobutyric acid (GABA) flows through, personal inhibitions fall away.

Sodium pentothal is formed by combining a complex ester and thiourea in a two step process. The complex ester is diethyl malonate with a 1 Šmethyl-butyl group and a ethyl group on the secondary (central) carbon. This complex ester, diethyl 2-ethyl-2- (1-methylbutyl) malonate and thiourea go through nucleophilic acyl substitution to form pentothal. The sodium salt of pentothal is then formed by a hydrogen abstraction on the N-H group by sodium hydroxide (NaOH). The proper reaction is shown.

While sodium pentothal may not be a miraculous solution for extracting information, it does have potential. Some think itÕs a long shot, but that it might work. Can you get search warrants to search a person's mind? This is an issue that the courts have never thought about. Court experts said the subject opens up fresh legal veins. The courts must consider that the information acquired may be able to save lives.

Pertinent Text References

Chapter 21. Ester Enolates (Carey 4/e) pg. 845-846
Study Guide and Solutions Manual (Carey 4/e) pg. 581-582

Follow Up Information

High Incident: Sodium Pentothal
Synthesis of Diethyl Malonate


Question 1: Diethyl 2-ethyl-2- (1-methylbutyl) malonate has two ester groups. Locate them.

Answer: See Picture of Reaction. List of Functional Groups

Question 2: What other product is formed when NaOH is mixed with pentothal?

Answer: Proton abstraction by hydroxide gives water.

Question 3: When was sodium pentothal first discovered, and by whom?

Answer: See Article. Sodium pentothal was discovered in 1936 in Chicago by Abbott Laboratories' researchers Ernest H. Volwiler and Donalee L. Tabern.

Question 4: How credible is information extracted from drugged individuals?

Answer: See Article. Sodium pentothal loosens inhibitions but has not been proven to make patients tell the truth, so the credibility of statements is very controversial.

Chemistry & Society Discussion.
With the detainment of many terrorists who may hold valuable information, the ethics of using chemicals such as sodium pentothal may arise. Do you think the government should use chemicals to "search" the minds of other people?