Cocaine, extraction

Fish and Wilson17 worked out a method for the determination of cocaine in urine by extraction of the urine with diethyl ether after addition of hydrochloric acid to remove impurities, followed by addition of sodium bicarbonate to give pH 8 (approx.) and further extraction of the cocaine with diethyl ether, concentration of the diethyl ether extract and GLC. Benzhexol was utilized as an internal standard. The reproducibility of the gas chromatographic determination of cocaine extracted from urine is seen in Table 9.2. 

REPRODUCIBILITY OF THE GAS CHROMATOGRAPHIC DETERMINATION OF COCAINE EXTRACTED FROM URINE17... 

Cocaine, extracted from Erythroxylon coca and used as a nerve stimulant and anaesthetic. 

Not only did the Pope endorse it, he awarded Vin Mariani a gold medal Imitation being the sincerest form of flattery, a Georgian pharmacist named John Styth Pemberton created his own version of Mariani s concoction, called French Wine Cola . Prohibition came to Atlanta in 1886, so Pemberton created a new nonalcoholic version of the drink which he called Coca-Cola. In 1903, the cocaine extract was removed from the recipe, being replaced by sugar and caffeine to supply the stimulant, although the name Coca-Cola remained unchanged. 

Other uses include use as a reaction and extraction solvent in pharmaceutical production as an intermediate for the preparation of catalysts, antioxidants (qv), and perfumes and as a feedstock in the production of methyl isopropenyl ketone, 2,3-butanedione, and methyl ethyl ketone peroxide. Concern has also arisen at the large volume of exported MEK which has been covertly diverted and used to process cocaine in Latin American countries... 

Cocaine comes from the Coca plant, grown in the high arid, mountainous areas of South America. It is usually extracted from the leaves of the plant but the leaves themselves can be chewed and a smokable paste made from the leaves is mainly used in countries where the plant grows. 

Another of the main systemic routes is oral (Table 3.2). Sometimes raw plant material is chewed in order to release the psychoactive compound into the mouth cavity. Examples include the chewing of coca leaves to extract cocaine (Chapter 4) and the tobacco leaf to extract nicotine (Chapter 5). The problem with this is that many other plant chemicals remain in the mouth, and many of these are carcinogenic. Tobacco leaf chewing leads to oral cancers of the mouth, lips, jaw and tongue, often... 

Cocaine A potent psychostimulant with local anaesthetic properties extracted from the South American plant Erythroxylon coca. 

Drugs have been purified by SPE in the analysis of amphetamine (AM) by Kaleta et al. [98], by various consecutive washing steps with hexane in the analysis of methamphetamine (MA) by Jones-Lepp and Stevens [99], and by simple centrifugation after addition of water, to separate the aqueous extract from a bottom sediment layer and a top fat layer, in the analysis of AM, MA, cocaine (CO), and benzoylecgonine (BE) by Langford et al. [100], who found little improvement in reducing matrix effects when applying SPE cleanup. 

Brachet A, Christen P and Veuthey J. 2002. Focused microwave-assisted extraction of cocaine and ben-zoylecgonine from coca leaves. Phytochem Anal 13(3) 162-169. 

Sample preconcentration was performed by means of an automated on-line SPE sample processor Prospekt-2 (Spark Holland, Emmen, The Netherlands). Oasis HLB cartridges (Waters, Barcelona, Spain) were used to preconcentrate cannabi-noids present in the water samples whereas isolation of the rest of the compounds was done in PLRPs cartridges (Spark Holland). Before extraction, influent samples were diluted with HPLC water (1 9, v/v) to reduce matrix interferences and to fit some analyte concentrations, e.g., cocaine (CO) and benzoylecgonine (BE), within the linear calibration range. A sample volume of 5 mL was spiked with the internal standard mixture (at 20 ng/L) in order to correct for potential losses during the analytical procedure, as well as for matrix effects. Elution of the analytes to the LC system was done with the chromatographic mobile phase. 

Gheorghe A, Van Nuijs A, Pecceu B, Bervoets L, Jorens PG, Blust R, Neels H, Covaci A (2008) Analysis of cocaine and its principal metabolites in waste and surface water using solid-phase extraction and liquid chromatography-ion trap tandem mass spectrometry. Anal Bioanal Chem 391 1309-1319... 

Coca-cola got its name from the coca leaf extract which it contained (as did a variety of wines) until 1904. Neither tolerance nor physical addiction to cocaine seem to occur, so sniffing it occasionally should be quite safe. 

Cocaine can be extracted from the leaves with almost any organic solvent. Moisten the dried, powdered leaves with Na carbonate solution and extract with cold benzene or petroleum ether. Extract the organic solution with small amounts of dilute sulfuric acid and basify the extract with Na carbonate (the alkaloids precipitate). Dissolve the precipitate in ether, separate the ether from the aqueous Na carbonate and dry and evaporate in vacuum the ether. Dissolve the residue in methanol and heat with sulfuric acid or methanol-HCl dilute with water and extract with CHC13. Concentrate and neutralize the aqueous layer and cool to precipitate methylecgonine sulfate, which is converted to cocaine in one step. The alkaloids can also be extracted directly from the powder with dilute sulfuric acid. 

Dissolve 1 g coca paste in 10 ml 3% sulfuric acid, cool to 0° and add with stirring 8 ml 6% KMn04 and 10% sulfuric acid, 1 ml at a time over one hour. Let stand /a hour and add powdered oxalic acid with stirring until the precipitate which has formed dissolves. Extract two times with ether, basify the aqueous solution with NH4OH and extract four times with 18 ml ether. Dry and evaporate in vacuum the ether to get cocaine. The aqueous solution contains ecgonine, which can be converted to cocaine as shown below. 

Alternatively, mixture of 4 g (V), 36 ml benzene, 1.6 g Na carbonate and 7 ml benzoyl-Cl stir and heat 96-100° for ten hours. Evaporate in vacuum, cool to 0° and add 40 ml ice water. Acidify with HCI to pH 5 and extract with 3X20 ml ether. Neutralize the aqueous solution with 20% NH4OH to separate an oil from which cocaine precipitates on standing (from JGC 30,3228(1960)). 

Mixture of 1.35 g Na methoxide (Na in methanol), 3.48 g tropinone (which can be obtained by K dichromate oxidation of tropine), 4 ml dimethylcarbonate and 10 ml toluene. Reflux /2 hour, cool to 0° and add 15 ml water containing 2.5 g NH4CI. Extract with 4X50 ml CHCI3, dry and evaporate in vacuum and dissolve the oil in 100 ml ether. Wash two times with a mixture of 6 ml saturated aqueous K carbonate and 3 ml 3N KOH (dry and evaporate in vacuum the ether to recover unreacted tropinone). Take up the oil which separates in saturated aqueous NH4CI and extract it with CHCI3. Dry and evaporate in vacuum to get an oil which is dissolved in hot acetone. Cool, add a little water and rub to start precipitation of 1.5 g 2-carbomethoxytropinone. This is identical with (IV) of method 1, and can be recrystallized and converted to cocaine as already described. 

The coca leaf is either consumed by the natives of South America or exported to other countries for consumption. Another use of the coca leaf is in the extraction of cocaine either for illegitimate or legitimate use. The majority of the legal and/or clandestine cocaine factories are in South America due to the cost and bulk of transporting the whole leaf. In 1961, Bolivia produced an annual crop of from 12,000 to 18,000 tons of leaves although only half reached the legal market. The alkaloid cocaine is extracted from the coca leaf in basically three different chemical procedures. These procedures are used both in licit and illicit labs in the production of cocaine. 

According to a chemist who assisted in the legal manufacture of cocaine, there are three basic methods of extracting cocaine from the coca leaf ... 

The Peruvian coca leaves, because of their richness, are commonly used in the extraction process as described in 1 or 2. When the dried coca leaves have a low cocaine content, the ecgonine process is preferred. Normally, it takes approximately 100 pounds of dried leaves to produce one pound of cocaine. 

A chemist from the Federal Bureau of Narcotics and Dangerous Drugs, who was in Bolivia to observe clandestine cocaine operations, related the following step-by-step procedure for manufacturing cocaine. The method can be conveniently divided into three major steps (1) extraction of cocaine from the leaf and chemical conversion to the sulfate (2) treatment of cocaine sulfate with potassium permanganate and conversion to the free base (aka paste) and (3) conversion of the paste or free base to cocaine hydrochloride. In general, steps (1) and (2) are carried out in sulfate labs while step (3) is performed in crystal labs. 

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