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PubMed1982

The effects of field preservation on alkaloid content of fresh coca leaves (Erythroxylum spp.).

In order to test the effects of commonly used preservation agents on the alkaloid content of herbarium specimens, fresh leaves of Erythroxylum coca, E. novogranantense, and E. novogranatense var. truxillense were air-or heat-dried or treated with six different liquid preservatives. The leaves were then extracted and analyzed quantitatively for cocaine content. Leaves which were soaked in preservatives showed appreciable pre-extraction of cocaine and probably of other alkaloids. The results compare well with a similar experiment conducted on flavonoid content of the leaves of a palm Jessenia bataua. If portions of herbarium specimens are to be useful for phytochemical screening using microtechniques, at least part of the collection must be air- or heat-dried to retain the chemical constituents.

Alkaloids↗
PubMed1987

Capillary gas chromatographic-electron capture detection of coca-leaf-related impurities in illicit cocaine: 2,4-diphenylcyclobutane-1,3-dicarboxylic acids, 1,4-diphenylcyclobutane-2,3-dicarboxylic acids and their alkaloidal precursors, the truxillines.

A method has been developed that allows for the detection of the eleven stereoisomers of diphenylcyclobutanedicarboxylic acid in illicit cocaine samples, including alpha-, gamma-, and epsilon-truxillic acids and beta- and delta-truxinic acids. These, and other carboxylic acids, were also detected as ester moieties of alkaloidal impurities in illicit cocaine as well as in alkaloids of the South American coca leaf, e.g., alpha- and beta-truxilline. After lithium aluminum hydride reduction of the acidic and basic extracts of a prepared sample, the reduced species were derivatized with heptafluorobutyric anhydride in the presence of pyridine. The heptafluorobutyryl derivatives of the reduced diphenylcyclobutanedicarboxylic compounds were easily detected on-column at low picogram levels using a moderately polar fused-silica capillary column in the splitless mode and interfaced with a 63Ni electron-capture detector.

Alcohols↗
PubMedDate not supplied

2,3-Dehydrococaine: not a direct precursor of cocaine in Erythroxylum coca.

(+/-)-3-[4(-3)H]Benzoyloxy-2-[carbonyl-13C, 14C]carbomethoxy-2-tropene (2,3-dehydrococaine) was synthesized from Ba [13C, 14C]CO3 and [4(-3)H]benzoic acid. This labeled compound (3H/14C 0.65) was administered to Erythroxylum coca plants for 3 and 15 days. After these times, cocaine was isolated and was found to have a 3H/14C ratio quite different from the administered dehydrococaine (3.0 and 10.6 for the 3- and 15-day feeding experiments, respectively). Degradations of the cocaine indicated that tritium was all located in the 4-position of its benzoyl moiety. 13C-nmr spectroscopy indicated enrichment of the carbomethoxy group of cocaine, consistent with the observed specific incorporation of the 14C. From the 3-day feeding experiment unmetabolized dehydrococaine was isolated having the same specific activity and 3H/14C ratio as the administered compound. Also from this feeding experiment 2-carbomethoxy-3-tropinone was isolated having about 1/3 the specific activity (14C) of the administered dehydrococaine and having a (-) optical rotation. These results indicate that cocaine is not formed by the direct reduction of dehydrococaine. The results indicate that cocaine is not formed by the direct reduction of dehydrococaine. The results are rationalized by proposing initial hydrolysis of the dehydrococaine to benzoic acid and 2-carbomethoxy-3-tropinone. The latter compound is then reduced to methyl ecgonine, which is then esterified with benzoic acid to yield cocaine. The change in the 3H/14C ratio is due to the fact that only the (+) enantiomer of 2-carbomethoxy-3-tropinone is converted to cocaine, and that different pool sizes of the non-labeled intermediates exist in the plant.

Chemical Phenomena↗
PubMed2006

Evaluation of solid-phase microextraction desorption parameters for fast GC analysis of cocaine in coca leaves.

By its simplicity and rapidity, solid-phase microextraction (SPME) appears as an interesting alternative for sample introduction in fast gas chromatography (fast GC). This combination depends on numerous parameters affecting the desorption step (i.e., the release of compounds from the SPME fiber coating to the GC column). In this study, different liner diameters, injection temperatures, and gas flow rates are evaluated to accelerate the thermal desorption process in the injection port. This process is followed with real-time direct coupling a split/splitless injector to a mass spectrometer by means of a short capillary. It is shown that an effective, quantitative, and rapid transfer of cocaine (COC) and cocaethylene (CE) is performed with a 0.75-mm i.d. liner, at 280 degrees C and 4 mL/min gas flow rate. The 7-microm polydimethylsiloxane (PDMS) coating is selected for combination with fast GC because the 100-microm PDMS fiber presents some limitations caused by fiber bleeding. Finally, the developed SPME-fast GC method is applied to perform in less than 5 min, the quantitation of COC extracted from coca leaves by focused microwave-assisted extraction. An amount of 7.6 +/- 0.5 mg of COC per gram of dry mass is found, which is in good agreement with previously published results.

Chromatography, Gas↗
PubMedDate not supplied

Cocaine and metabolite concentrations in the hair of South American coca chewers.

Hair samples obtained from South American Indians who were identified as daily chewers of coca leaves were analyzed by a sensitive gas chromatography/mass spectrometry (GC/MS) method for cocaine, benzoylecognine (BE), and ecognine methyl ester (EME). The mean cocaine concentration in the hair of these five subjects was 15.2 ng/mg hair +/- 11.0 (range = 1.0-28.9 ng/mg), mean BE concentration was 2.8 +/- 1.6 ng/mg hair (range = 0.3-4.4 ng/mg hair), and mean EME concentration was 1.6 +/- 1.7 (range = 0.0-4.4 ng/mg hair). The finding that cocaine was present at approximately 5 times higher concentration than BE and approximately 12 times higher than EME is surprising in light of the much longer plasma half lives of these metabolites. Washing the hair before analysis with 1% dodecyl sulfate, methanol, and distilled water reduced the concentration of cocaine in the hair but also reduced the concentrations of the metabolites. These data suggest that factors other than the drug concentration in blood may be important in determining the amount of drug incorporated into hair.

Coca↗
PubMedDate not supplied

Identification and quantitation of cocaine and its metabolites, benzoylecgonine and ecgonine methyl ester, in hair of Bolivian coca chewers by gas chromatography/mass spectrometry.

Twenty hair samples obtained from Bolivian mine workers who chewed 3-8 g of coca leaves daily for several years were analyzed for cocaine and its main metabolites, benzoylecgonine (BZE) and ecgonine methyl ester (EME). A new method was developed for the detection and quantitation of cocaine and its metabolites, BZE and EME, from hair in a single procedure. The hair samples were washed, cut into 56 segments (2-cm length), pulverized, and incubated with phosphate buffer and the enzyme beta-glucuronidase-arylsulfatase. After solid phase extraction and derivatization with pentafluoropropionic anhydride/pentafluoropropanol, the drugs were identified and measured by gas chromatography/mass spectrometry (GC/MS) using deuterated cocaine, BZE, and EME as internal standards. The method is reproducible (cocaine, CV = 8%; BZE, CV = 14%) and the detection limit for cocaine and BZE was 0.1 ng/mg, for EME 1 ng/mg. In the different hair segments, cocaine was found to be present in concentrations between 1.4 to 50.6 ng/mg, benzoylecgonine from 0.4 to 17.6 ng/mg, and ecgonine methyl ester traces below the calibration curve of approximately 12.9 ng/mg. In 95% of the cases cocaine exceeded BZE and EME in concentration.

Adolescent↗
PubMed1988

Effects of extended feeding of decocainized erythroxylon coca leaves on growth and selected organs in rats and rabbits.

Erythroxylon coca leaves from the Trujillo area of Peru were extracted with methylene chloride to remove most cocaine-like alkaloids. The decocainized leaves were formulated in a honey-water vehicle and fed on a chronic basis to female rats for 32 weeks and female rabbits for 13 weeks. Rabbits fed decocainized leaves at doses of 21 or 210 mg demonstrated no significant change in growth (weight gain) when compared with those receiving vehicle. Histological findings were unremarkable except for fatty islands in the myocardium. Rats fed the decocainized leaves at doses of 1.5 and 15 mg demonstrated no significant changes in weight, whereas those receiving 150 mg had a significant decrease in weight gain when compared with control animals receiving vehicle. Necropsy findings in rats demonstrated pyometra in all groups receiving decocainized leaves as well as in some of the controls. Those rats with pyometra often exhibited endometrial metaplasia. Renal tubular calcification and proteinaceous material were consistently noted at all dose levels. Portal triaditis was also found in the livers of most rats.

Alkaloids↗
PubMed1992

Environmental impact of coca cultivation and cocaine production in the Amazon region of Peru.

Little or nothing has been written about the environmental consequences of the cultivation of coca and the production of basic cocaine paste. Nevertheless, there is much evidence that both activities have a severe and irreparable impact on the ecosystems in which they are carried out. This chapter describes the situation in the Peruvian Amazon, discusses the consequences of these activities, and recommends measures to improve current conditions.

Agriculture↗
PubMed1976

[Isolation of the Derivatives from Coca-Powder Fumigated by Ethylene Oxide 1,2-14 C and their Structure Suggested on the Basis of I. R. and Mass-Spectrometry].

In Coca-powder fumigated with Ethylene Oxide-1,2(14)C, several derivatives were isolated by extraction and preparative Thin Layer Chromatography. Of the two compounds isolated from the water-extract, the structures have been suggested as N,N-Bis-(Di-Ethoxy-O-Hydroxy-ethyl)-Isoleucyl-Alanyl-Cysteine (MW = 569)and N-Ethoxy-O-Hydroxyethyl)-Tyrosine (MW = 269), based on I.R. and Mass Spectrometry. Their approximate concentrations were found to be 20 and 50 mg/kg respectively.

Amino Acids↗
PubMed1993

Cocaine and metabolites in the hair of ancient Peruvian coca leaf chewers.

Cocaine and its metabolites, benzoylecgonine (BZE) and ecgonine methylester (EME), were found in hair samples from ancient Peruvian coca-leaf chewers dating back to AD 1000. Hair was analyzed by gas chromatography/mass spectrometry (GC/MS) to quantitate the concentrations. The two metabolites were found in higher concentration than the parent drug. The metabolite levels appear to be below that of modern cocaine abusers. Gender does not appear to be a factor in the incorporation of drug into hair.

Adult↗
PubMed2002

Gastric phytobezoars may be treated by nasogastric Coca-Cola lavage.

Large gastric phytobezoars may occur in patients with gastric dysmotility disorders. Treatment options include dissolution with enzymes, endoscopic fragmentation with removal or aspiration, and surgery. We report our experience with nasogastric cola lavage therapy. Over an 8-year period, five consecutive patients were referred to our unit for endoscopic treatment of large gastric phytobezoars. They included one patient with lobectomy for lung cancer and four patients with diabetic gastroparesis. An initial attempt of endoscopic fragmentation and removal was unsuccessful. Patients were treated with 3 l of Coca-Cola nasogastric lavage over 12 h. Nasogastric lavage was very well tolerated by the patients. Complete phytobezoar dissolution was achieved in one session in all cases. There were no procedure-related complications. The dissolution of large gastric phytobezoars with cola nasogastric lavage is a safe, rapid and effective method. Patients may be treated in the medical ward, avoiding therapeutic endoscopy or surgery.

Aged↗
PubMed1984

Duodenal pH in health and duodenal ulcer disease: effect of a meal, Coca-Cola, smoking, and cimetidine.

Intraluminal duodenal pH was recorded using a combined miniature electrode and logged digitally every 10 or 20 seconds for five hours (basal/meal/drink) in eight control subjects and 11 patients with duodenal ulcer (five on and off treatment with cimetidine). Over the whole test there were no significant differences in duodenal mean pH or log mean hydrogen ion activity (LMHa) between control subjects and patients with duodenal ulcer, but there were significantly longer periods of duodenal acidification (pH less than 4) and paradoxically more periods of duodenal alkalinisation (pH greater than 6) in the duodenal ulcer group compared with controls. After a meal duodenal mean pH and LMHa fell significantly in both controls and patients with duodenal ulcer, with more periods of duodenal acidification and alkalinisation in the duodenal ulcer group. An exogenous acid load (Coca-Cola) significantly increased the periods of duodenal acidification, and reduced alkalinisation, in both groups. Cimetidine significantly increased mean pH and LMHa and abolished the brief spikes of acidification in four of five patients with duodenal ulcer. Peak acid output (but not basal acid output) was significantly correlated with duodenal mean pH and LMHa but not with the periods of duodenal acidification. Smoking did not affect duodenal pH in either group.

Adult↗
PubMed2006

[Phytobezoar dissolution with Coca-Cola].

The treatment of phytobezoar is empiric. The various therapeutic choices include dietary modifications, prokinetic drugs, gastric lavage, enzymatic dissolution, endoscopic treatment, and surgery. We present two cases of phytobezoar with successful outcome after Coca-Cola administration.

Aged↗
PubMed1987

The spermicidal potency of Coca-Cola and Pepsi-Cola.

The inhibitory effect of Old Coke, caffeine-free New Coke, New Coke, Diet Coke and Pepsi-Cola on human sperm motility was studied with a trans-membrane migration method. None of them could decrease sperm motility to less than 70% of control within one hour. A previous study which claimed a marked variation of spermicidal potencies among different formulations of Coca-Cola could not be confirmed. Even if cola has a spermicidal effect, its potency is relatively weak as compared with other well-known spermicidal agents.

Beverages↗
PubMed1991

Coca-Cola, cancers, and coronaries: personality and stress as mediating factors.

A theory is presented relating the consumption of stimulant and depressant drugs to cancer and coronary heart disease, with stress/personality acting as an intermediary. The predictions from the theory that large-scale consumption of Coca-Cola would prevent cancer and promote coronary heart disease was tested and found to be supported by the results of a long-scale prospective study. Results replicate those from an earlier study using coffee as a stimulant drug.

Alcohol Drinking↗
PubMed1991

Enamel softening with Coca-Cola and rehardening with milk or saliva.

Rehardening effects by cow's milk and by secreted saliva were investigated, in situ, following softening of human enamel with an acidic beverage (Coca-Cola). Volunteers wearing orthodontic removable appliances participated in the study. The intra-oral test was chosen for measuring microhardness of enamel slabs inserted into the dental appliance. The softening and the rehardening degrees were defined as the alterations between initial- and experimental-microhardness value at the enamel surface. In addition, SEM photos were prepared from the initial and experimental stages. Exposure of enamel slabs to the acidic beverage during 1 hour had a softening effect as expressed by the hardness decrease and visualized by the SEM photo. Rehardening effects following milk or saliva exposures respectively were evident, presumably due to deposited organic and mineral material on the enamel surface.

Adult↗