NARCOTIC
11 or above, whereas other opium alkaloids are relatively insoluble and generally precipitate out of basic aqueous solutions. "Codeine and thebaine are only present as trace amounts in poppy cultivated for Morphine wasfirstisolated in pure form the purpose of morphine extraction," Facfrom dried poppy resin by German apothe chini notes, approximately 95% of the cary Friedrich W Sertiirner (1783-1841) in morphine extracted from licit opium is the early 1800s. He named the compound chemically converted to codeine, a more '^οφΐιΐιιηι" after Morpheus—the Greek versatile pharmaceutical. The large quantigod of dreams. ties of morphine produced by the plant are In 1925, University of Oxford chemistry the basis for illicit cultivaprofessor Sir Robert Robin tion of opium poppy in son (1886-1975) proposed many regions of the world the correct structure of the for the synthesis of QO-dialkaloid following degrada acetylmorphine—heroin or tion studies of the com diamorphine. Illicit producpound. The molecule has a tion of opium exceeds licit pentacyclic structure with a usage by almost 10-fold." benzylisoquinoline nucleus supporting ether, hydroxyl, Morphine is commerand olefinic functions. cially available in a variety of products as the free base The 70 or so poppy species monohydrate and as hythat belong to the genus Padrochloride, sulfate, tartrate, paver biosynthesize around and other salts. The drug, 2,500 different benzyliso which is administered by quinoline alkaloids. The opi mouth or injection, is parum poppy contains more ticularly effective in rethan 80 alkaloids including lieving severe, continuous morphine and codeine (mor pain—for example, the pain phine monômethyl ether). experienced by patients The poppy also contains the with terminal cancer—withalkaloid thebaine, which is out loss of consciousness not an analgesic but is used to where other analgesics fail. produce semisynthetic opiIt also has a euphoric efoid morphine analogs such fect. On the downside, it as oxycodone. CULTIVATION causes severe constipation, Morphine is produced Commercial trial crops respiratory depression, commerciallyfromeither opi- of opium poppies were drowsiness, vomiting, loss um or concentrated poppy first grown in England of appetite, confusion, straw. Opium is a sticky in 2002. blurred vision, dry mouth, brown resin obtained by coland other adverse reactions. Morphine is leering and drying the latex that exudes from also highly addictive and induces tolerthe lanced poppy pods, whereas concenance, which means that higher and hightrated poppy straw is extracted from the er doses are required to maintain the same pods after the plants have been harvested. effect. "Over the last 20 years, India has supThe drug is a central nervous system deplied a relatively stable amount of about 600 tons of opium per annum for the ex- pressant that binds to and activates opitraction of alkaloids," says PeterJ. Facchi- oid receptors in the brain, spinal cord, and gut. It competes with endoφhins—the ni, professor ofplant biotechnology at the endogenous opioids in the body that at University of Calgary, Alberta. "Global protenuate pain—for the receptors. duction of poppy straw containing morMorphine occurs naturally as the (-) phine as the main alkaloid has fluctuated form. It was first synthesized in 1952 by between 30,000 and 52,000 tons per anchemists at the University of Rochester, num. The main producers of the straw are in New York {J. Amer. Chem. Soc. 1952,74, Australia, France, Spain, and Turkey" 1109). There have been a number of oth Morphine is extracted from opium resin er syntheses since, but it is highly unlikely or poppy straw in a series of extraction and that a practical synthesis that can compete purification steps involving water, organcommercially with biosynthesis in the opi ic solvents, andpH adjustment. Morphine um poppy will ever be achieved.—MICHAEL free base in its anionic (morphinate) form FREEMANTLE is soluble in basic aqueous solutions at pH
MORPHINE
M
O R P H I N E IS A MOLECULE
that can lay claim to being the original alkaloid and the first true drug, according to assistant professor Paul R. Blakemore and professor emeritus James D. White at Oregon State University, Corvallis (Chem. Commun. 2002,1159). Alkaloids are natural organic nitrogencontaining bases found mainly in plants. Morphine, a bitter white crystalline com pound, is the principal alkaloid in the opi um poppy Papaver somniferum. Traces of the compound, possibly from dietary sources, also occur in animal tissues and flu ids, including human heart tissue and urine. "The morphine story is one of the most enthralling in all of science," Blakemore and White note. "Early attempts to unlock the mysteries of opium provided a major stimulus to the development of organic chemistry and, it may be argued, spawned the entire field of medicinal chemistry" THE POTENT analgesic and euphoric prop erties of opium poppy pods have been known for thousands of years. Opium was used, for example, as a narcotic in Sumerian cultures in AsiaMinor as early as 4000 B.C. Its use and addiction were widespread in Roman times. In the 16th century the Swiss physician and alchemist Paracelsus (1493-1541) popularized its use in Europe with the introduction oflaudanum—a tinc ture, or alcoholic solution, of opium.
MORPHINE Name: (5a,6a)-7,8-Didehydro-4,5epoxy-17-methy[morphinan-3,6-diol CAS Registry: 57-27-2 Introduced: Poppy pods used as early as 4000 B.C. Regulated: In 19U, the Harrison Nar cotics Act was passed; it called for control of each phase of the prepara tion and distribution of medicinal opi um, morphine, heroin, cocaine, and any new derivative that could be shown to have similar properties. It made illegal the possession of these controlled substances. Did you know that in 1898, Bayer regis tered diacetylmorphine (diamorphine) under the proprietary name Heroin in Germany as a cough medicine for children?
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