Cocaine

Other Names Benzoylecgoninmethylester, cocain, cocaIn, cocaina, d-cocain, erythroxylin, kokain, methylbenzoylecgonine, methylbenzylekgonin, (±)-methyl- [3J3benzoyloxy- 2a( 1aH,5aH)-tropancarboxylate], 0benzoyl- [(- )-ekgonin] -methylester, 3-benzoyloxy8- methyl-8-azabicyclo [3.2.1] octan-2-carboxylicacidmethylester, 3J3 -benzoyloxy-2J3 -tropancarboxylicacid- methylester Street Names Autobahn, blow, C, candy, charlie, coca, coca pura (Spanish, "pure coca»), coco, coke, cousin, donuts, doppelter espresso, flake, koks, la blanca, lady snow, la rubiecita, line, linie, mama coca, nasenpuder, nose candy, peach, perica, puro (Spanish, "pure»), schnee, schneewittchen, schniefe, schnupfschnee, sniff, snow, snowwhite, strasse, strasschen, Ziggy's stardust Empirical formula: C17H21N04 Substance type: coca alkaloid The cocaine molecule is structurally related to tropine and other tropane alkaloids (Roth and Fenner 1988, 311*). Today, cocaine is the most consumed psychoactive plant constituent in the world. Pure cocaine (as a base) is not water soluble but can be dissolved in alcohol, chloroform, turpentine oil, olive oil, or acetone. Cocaine salts are water soluble. History In 1860, the German chemist Albert Niemann first isolated cocaine from the leaves of the Peruvian coca bush (Erythroxylum coca). The German pharmacist Friedrich Gaedeke (1855) may have represented the alkaloid before this. By around 1870, cocaine was being used as an agent of pleasure, and it was employed at this time to treat alcohol and morphine withdrawal as well as melancholy. The ophthalmologist Karl Koller, a friend of Sigmund Freud, introduced cocaine as a local anesthetic for eye surgery in 1884. Hermann Goring's use of cocaine was famous, and Adolf Hitler, who also used other stimulants (cf. strychnine), is thought to have consumed cocaine as well (Phillips and Wynne 1980, 112). Later, other substances derived from cocaine, including eucaine, procaine (= Novocaine), tetracaine (= Pantocaine) (1930), lidocaine (= Xylocaine) (1944), mepivacaine (= Scandicaine) (1957), prilocain (= Xylonest) (1960), bupivacaine (1963), and etidocain (= Duranest) (1972), were also used as local anesthetics (Busch and Rummel 1990; Schneider 1993, 19*). Holocaine was also regarded as a substitute. The goal of chemists and pharmacologists to carve out the effective core of the cocaine molecule and retain the desirable and remove the undesirable effects was achieved in an exemplary manner with the synthesis of procaine (1905). (Busch and Rummel 1990, 490) In 1923, Willstadter and his coworkers worked out the complete synthesis of cocaine. The precursors are succindialdehyde, methylamine, and mono-methyl-J3-keto-glutarate. However, this synthesis has never achieved pharmaceutical importance. Practically speaking, all of the cocaine used in the pharmaceutical industry is derived from the coca plant. In 1976,410 kg of cocaine were legally extracted for this purpose (Taschner and Richtberg 1982,64). Production and Use An analysis of thirteen South American Erythroxylum species found that cocaine is present only in Erythroxylum coca and Erythroxylum novogranatense (Holmstedt et al. 1977). Hair analysis of Egyptian mummies has revealed the presence of ecgonin, the first metabolite of cocaine, which indicates that the ancient Egyptians either consumed cocaine or an unknown African plant that metabolizes to ecgonin (Balabanova et al. 1992*). The coca plantations that are the source of cocaine are known as cocales. Bolivian huanaco leaves (Erythroxylum coca var. coca) are preferred for cocaine production because they are the highest yielding. With good chemicals and chemists, it is possible to produce 1 kg of pure cocaine from 100 kg of coca leaves. In the early 1980s, some 100 tons ofpure cocaine were exported from Colombia alone. The entire process of cocaine production, as well as the smuggling routes, the cartels, and everything from the connections between politicians and the cartels to the consumption of cocaine even by politicians in the White House, has been documented in countless reports on the radio and television and in magazines and well-researched books (Morales 1989). It is difficult to escape the impression that the cocaine saga is one of the bestknown stories of our times but one that is officially ignored. Our leaders still act as though the Mafia is using the white powder to corrupt and dominate the world. In reality, the chief benefactors of the billion-dollar business are the banks and the countless politicians and law-enforcement personnel involved in the trade (Sauloy and Le Bonniec 1994). The snuffing of crystallized cocaine appears to have been discovered in North America at the beginning of the twentieth century and spread from there. Shortly after 1900, pure cocaine was being ingested together with betel and lime in India, Ceylon (Sri Lanka), and Java. The use of cocaine as an athletic doping agent began in the 1940s (Fiihner 1943, 195*). Little has changed since that time. Cocaine dealers still find some of their best customers in the soccer stars of the German first league and sports heroes in the United States. Basuko is dried cocaine base (an intermediate step in the production of the pure alkaloid). Sucito, or joints made of basuko, have been smoked in Colombia since about 1930 (Siegel 1982b, 274). Cocaine is usually produced as a hydrochloride but sometimes also as an oxalate or hypochloride (HCL). Street cocaine is almost exclusively cocaine HCL. Most of the illicit cocaine available in Europe is only about 30% pure, as the expensive pure drug is usually "cut:' The substances that are most commonly used to "cut" cocaine are: • Inactive additives: milk sugar (lactose), grape sugar (glucose), baking powder, talc (talcum), borax, cornstarch, innositol, mannitol • Active additives: speed (amphetamine, fenetyllin, ritalin) and "freeze" (novocaine, benzocaine), PCP ("angel dust"), methedrine, pemoline, yohimbine, lidocaine, procaine, tetracaine, caffeine, quinine, heroin (Taschner and Richtberg 1982,65; Voigt 1982,84) Dosage A «line" of cocaine typically contains between 20 and 100 mg of cocaine, depending on the purity of the substance and the consumer's preference. Many users consume between 2 and 3 g in a day or night. It is said that «the first line of the day is the best." Ritual Use Cocaine has been called the champagne of drugs, the drug of high society, the drug of the rich, et cetera, and. it is certainly most often associated with the wealthier classes. As a result, consumption of the drug has taken on a strong social character. Cocaine is rarely used by one person alone. When it is taken with others, the consumption follows a rather well-defined ritual. The person providing the costly substance lays out several lines (preferably on a mirror), then takes a currency note (often of high value) and rolls it up. One end of the rolled bill is placed in a nostril and held with one hand, while the other hand is used to press the other nostril closed. Half of one line, or a small line, is then snuffed into the nostril. The person then switches nostrils and snuffs the remaining powder, after which the mirror is passed to the next person. This circle may be repeated several time, and it is customary for each of several participants to prepare lines from their own supply. Artifacts The cultural significance of cocaine in the modern world cannot be overlooked. Artists, musicians, and writers use it as a stimulant, while highly paid computer experts, software engineers, and programmers would hardly be able to keep up with the demands of their jobs without their «coke." Stockbrokers, financial gurus, and election staffers may use cocaine until they are ready to collapse. Even some of the soccer stars who jog into the stadium sporting T-shirts with such incongruous imprints as «Keine Macht den Drogen" C(No Power to Drugs") are high as a kite on cocaine. According to several estimates, the highest per capita consumption of cocaine is found in Silicon Valley and on Wall Street. The first literary treatment of cocaine is found in the Sherlock Holmes novel A Scandal in Bohemia, by Sir Arthur Conan Doyle, published only two years after Koller's discovery (Phillips and Wynne 1980, 45). In this book, the astonishing abilities of this brilliant detective are attributed in part to his use of cocaine. By the time of the following novel, The Sign of the Four, Sherlock Holmes is injecting the pure alkaloid intravenously (Voigt 1982,38). The most famous novel of the British writer Robert Louis Stevenson, Dr. Jekyll and Mr. Hyde, was written in only four or six days and nightswith the assistance of the magic powder, of course (Springer 1989,8; Voigt 1982,38). The novellas of the expressionist poet Walter Rheiner (1895-1925), in which he referred to the drug as «the eternal poison" and «the loved and hated poison," played a great role in shaping the image of demonic seduction by pharmaceutical cocaine (Rheiner 1979). At the beginning of the twentieth century, the physician Gottfried Benn (1886-1956) wrote and published numerous poems about cocaine (of which he was very fond) that at the time were deemed rather shocking (Benn 1982; vom Scheidt 1981, 401). Many other authors have also been inspired by cocaine, including Georg Trakl, Thomas Zweifel, Josef Maria Frank Fritz von Ostini, Klaus Mann, and Jean Cocteau (Springer 1989). Cocaine is also the subject of many novels. The classic cocaine novel, Cocaine, was written by Pitigrilli (= Dino Serge, 1927). The drug has often been treated within its current criminal context (Badekerl 1983; Fauser 1983), while other novels have been written from a futuristic perspective (Boye 1986). The "coke scene" has also provided a rich source of literary inspiration (McInerney 1984; Ellis 1986). The composer Richard Strauss (1864-1949) wrote his opera Arabella while under the influence of cocaine (Springer 1989,8; Timmerberg 1996).494 Countless compositions have had cocaine as their subject, including Cocaine IiI, for a mezzosoprano and four female jazz singers, by the contemporary composer Nancy van de Vate (CD Ensemble Belcanto, Koch, 1994). From the 1920s to the 1940s, the white powder fueled the work of especially jazz and blues musicians, and Chick Webb, Luke Jordan, and Dick Justice even gave it a musical treatment ("Cocaine Blues"). Veritable blizzards of cocaine have passed through the brains of many of rock music's greats, who then set their experiences with the "fuel" to music. A few examples are Country Joe McDonald ("Cocaine"), Black Sabbath ("Snowblind"), Little Feat C'Sailin' Shoes"), the Rolling Stones ("Let It Bleed"), Jackson Browne ("Cocaine"), and David Bowie ("Ziggy Stardust"). The "hippie" band known as the Grateful Dead sang about the white powder in their song "Truckin'," one of their few hits to make it onto the charts. Eric Clapton's interpretation of J. J. Cale's song "Cocaine" became a worldwide success and has been played millions of times over. The reggae artist Dillinger released an album named Cocaine. The drug also left its mark on the German music scene, influencing or even appearing in the music of Hannes Wader, Konstantin Wecker, Abi Ofarim, and T'MA a.k.a. Falco ("Mutter, der Mann mit dem Koks ist da" ["Mother, the Man with the Coke Is Here"]; BMG Records 1995). Cocaine has been the subject of at least one theater work: The American playwright Pendleton King wrote a piece entitled Cocaine that was produced for the stage in 1917 (Phillips and Wynne 1980,93 ff.). Medicinal Use The medicinal applications of cocaine were discovered only a short time after the isolation of the molecule itself. Cocaine was initially used for local anesthesia495 in ophthalmology and dentistry, and infiltration anesthesia was developed just a few years later (Custer 1898). Because analogs (e.g., procaine) were developed that produce specific effects with no psychoactive side effects, cocaine is rarely used as an anesthetic today.

Pharmacology and Effects Cocaine stimulates the central nervous system, especially the autonomic (sympathetic) system, where it inhibits the reuptake of the neurotransmitters noradrenaline, dopamine, and serotonin and increases the time in which they remain in the synaptic cleft. Cocaine has a powerful effect upon the peripheral nervous system, which explains its efficaciousness as a local anesthetic. It has strong stimulant and vasoconstricting properties. Very high dosages of cocaine are said to be able to induce hallucinations, an effect that is frequently noted in the neurological literature (Pulvirenti and Koob 1996,49) as well as in prose and poetry (Rheiner 1979, 27). Hallucinations (of nonexistent people, images, flickering lights) often occur during nights in which dosages of 2 to 3 g have been taken. For many people, cocaine also dispels fear. It stimu1ates a need for alcoholic beverages at the same time that it strongly suppresses the effects of alcohol. A similar dynamic applies to nicotine. In a certain sense, there is something unsatisfying about the effects of cocaine. A person may sense that satisfaction could be achieved if the effects could possibly be increased. However, using more cocaine does not produce an enhancement of its effects. Just as coca was and is employed in South America as an aphrodisiac, cocaine has a similar use in the West. Cocaine's reputation as an aphrodisiac can be traced back to Sigmund Freud (1884) and has been repeatedly confirmed in the pharmacological literature: At a high level of intoxication, central excitation sets in with characteristic shivering, an initial state of euphoria that turns into delirium and hallucinations. For women, the stimulation ... not infrequently has an erotic character and has resulted in later accusations of sexual misconduct against the operating physician. (Fiihner 1943, 196*) Some psychiatrists believe that cocaine stimulates the "sexual center" of the brain (Siegel 1982a). For many users, cocaine is inevitably associated with sexuality (MacDonald et al. 1988; Phillips and Wynne 1980,221). Cocaine relaxes and opens the sphincter muscles, which makes anal penetration easier as well as substantially more pleasurable. However, cocaine (much like ephedrine) often has an adverse effect on erectile function and consequently leads to temporary impotence (cf. Siegel 1982a). The addictive potential of cocaine has been the subject of much debate. This issue does not appear to be oriented toward the user as much as it reflects the current legal situation. In recent years, there have been efforts to develop a vaccination against "cocaine addiction." Of course, the research in this area is conducted on rats (Hellwig 1996). The effect of cocaine on the brain is also an object of much research, since studies that confirm the adverse effects of cocaine are likely to receive financial support from the government. Studies that do not have a political agenda are the exception rather than the rule (Volkow and Swann 1990). People who use cocaine frequently suffer from a runny nose ("coke sniffles") the following day. Users may counteract this undesirable and unpleasant aftereffect by rinsing their nose with a saline solution (e.g., with medicinal salts). Many users rub vitamin E oil in their nose, a practice said to regenerate the highly irritated mucous membranes in the nose (Voigt 1982,72). Although cocaine can be very helpful in dealing with an acute attack of hay fever, chronic use can actually contribute to the condition. Crack or Free-Base Cocaine In the German press, crack has been portrayed as "death for a few dollars," "the devil's drug from the U.S.A.;' et cetera. The general idea seems to be that "cocaine was a miracle, but crack, crack was better than sex" or "cocaine was purgatory-but crack is hell" (in Wiener 6 [1986]: 65,66). Crack, which is also known as base, free base, baseball, rocks, Roxanne, and supercoke, is nothing more than smokeable free-base cocaine (Siegel 1982b). In other words, crack is cocaine in the form of a free base (Pulvirenti and Koob 1996, 48). It can be obtained from an aqueous solution of cocaine hydrochloride to which an alkaline substance (such as sodium carbonate) is added. The cocaine salt is transformed into the pure base, or, in other words, the pure substance. It can then be purified with ether, causing the cocaine to crystallize out. Crack is usually "smoked" (i.e., vaporized and inhaled) in glass pipes. A typical dosage ranges from 0.05 to 0.1 g. The effect is very similar to that of snuffed cocaine but is much more intense: Although crack is a derivative of cocaine, there is little comparison between the mild and mostly stimulating cocaine inebriation and the effects of the short-term crack high, which can literally bowl one over. Whereas cocaine produces a euphoric sensation of great concentration and razor-sharp intelligence for about 20 to 60 minutes, crack lasts for only three to five minutes while giving the consumer an incredibly strong kick with regard to physical sensations as well as the euphoria of absolute omnipotence. Of course, this has resulted in many myths, including one that crack is particularly pure. (Sahihi 1995,37*) Ethnologists have begun using the field methods typical of the discipline to study the "crack phenomenon;' which appears to be a typically American product (Holden 1989). "Crack life" is a reflection of the problems in American society and reveals deep social fissures and cultural anomalies. For users, the "crack way" is an important form of identity formation. Crack is frequently found together with prostitution, as "addicts" may accept it as a form of payment for sexual services (Carlson and Siegal 1991). On the street, the following substances may be used as substitutes for cocaine or crack in times of shortage: procaine, caffeine, benzocaine, phenylpropanolamine, lidocaine, and ephedrine (Siegel 1980). Commercial Forms and Regulations Cocaine hydrochloride is available through the pharmacy trade. The German Drug Law lists cocaine as a "narcotic drug in which trafficking is allowed but which may not be prescribed" (Korner 1994, 42). In the United States, the Controlled Substances Act classifies cocaine as a Schedule II substance. Literature See also the entries for Erythroxylum coca, Erythroxylum novogranatense, atropine, and tropane alkaloids. Ashley, Richard. 1975. Cocaine: Its history, use and effects. New York: St. Martin's Press. Aurep, B. von. 1880. 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