Current Topics in Chemistry - Bruice

Dr. Glaser's "Chemistry is in the News"
To Accompany Bruice, Organic Chemistry, 3/e.
Chapter 27. Heterocyclic Compounds.

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

FEDERAL DRUG ENFORCERS REPORT RISE IN USE OF METHAMPHETAMINE
by Nicole Tsong (Hearst Newspapers, June 26, 1998)

Editorial Comments

Nicotine, cocaine, morphine and heroin are alkaloids. Alkaloids are natural products, they usually occur in plants, and they contain one or more N-atoms typically in a heterocycle. Alkaloids often have pronounced pharmaceutical effects. The alkaloids are produced by way of isolation from the plants in which they occur naturally. Nicotine occurs in tobacco leaves and cocaine is extracted from coca plants. The free base of cocaine is "crack" cocaine and the hydrochloride salt is referred to as "snow" cocaine. Morphine is obtained from the opium juice of some poppy plants. Heroin is acetylated morphine.

These alkaloids are difficult to make from scratch. Total synthesis of these molecules are known but they are too complicted and too expensive and synthesis cannot compete with the isolation of the natural products. Controlling the drugs cocaine, morphine and heroin (a morphine derivative) reduces to controlling the crops and their transportation.

And now there is methamphetamine as the big drug. Methamphetamine is a highly addictive and immensely destructive drug and methamphetamine abuse and addiction are well documented. Methamphetamine also is called "speed" reflecting the energy boost it delivers. Some call it "ice" since pure methamphetamine comes in crystals that look just like ice crystals. (Talk about an oxymoron! Ain't nothing cool about this stuff.)

Speed is a very different drug in that its structure is comparatively simple and speed is therefore easily accessible by synthesis. Amphethamine is an aromatic compound: Benzene with an n-propyl side chain which is substituted in the 2'-position by an amino group. In methamphetamine the amino group also carries a methyl group. This drug is much harder to control as it can be synthesized anywhere and basically by just about anybody.

Pertinent Text References
Chapter 14. Aromaticity. Reactions of Benzenes.
Chapter 15. Reactions of Substituted Benzenes.
Chapter 27. Heterocyclic Compounds.
Chapter 29. More about Multistep Organic Synthesis.

Questions

Question 1: What is the structure of "ephedrine"? How is this compound available on the market?

Answer 1: Ephedrine differs from methamphetamine only in the presence of one hydroxyl group on the C-atom that connects the side chain to the benzene. Ephedrine is a bronchodilator.

Question 2: How can the conversion of "ephedrine" to speed be accomplished?

Answer 2: Reduction of ephedrine with lithium in liquid ammonia or with red phosphorus and HI affords methamphetamine.

Question 3: What are the short-term and the long-term effects of methamphetamine?

Answer 3: See NIDA report.

Question 4: How is methamphetamine different from other stimulants such as cocaine?

Answer 4: See NIDA report.

Chemistry & Society.
Review the section on "How is methamphetamine different from other stimulants, like cocaine?" of the NIDA report. Although methamphetamine and cocaine both are psychostimulants, there significant differences between these drugs. Which features make methamphetamine so "attractive"?