Heroin, was first commercially synthesized in 1898 by Bayer company in Germany as an alternate analgesic to morphine. Heroin is the 3,6 diacetylated form of morphine (Fig. 24.7). The laboratory researchers, which also used the acetylation process to convert salicylic acid into acetyl salicylic acid (aspirin), believed that heroin would be an effective analgesic with no addictive properties. This was unfortunately not the case. They named the product "heroin" because it made the test subjects, including some of the chemists, feel "heroic." With both OH groups protected as an ester, heroin can pass through the blood-brain barrier quicker than morphine and lead to the euphoric "rush" that becomes so addictive to addicts, especially after IV injection. Once heroin is in the brain, it is quickly metabolized to 3-acetylmorphine, which has low to zero activity at the /-receptor and 6-acetylmorphine, which is 2 to 3 times more potent at the /-receptor than morphine.62
Heroin is not available as a prescription product in the United States, although it is available in some countries to treat pain associated with cancer and myocardial infarctions. It remains one of the most widely used narcotics for illicit purposes and places major economic burdens on society.
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