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PubMed2002

Enantioselective synthesis of (-)-codeine and (-)-morphine.

A new synthetic strategy for the synthesis of the opiate and amaryllidaceae alkaloids emerges employing a Pd-catalyzed asymmetric allylic alkylation to set the stereochemistry. The pivotal tricyclic intermediate is available in six steps from 2-bromovanillin and the monoester of methyl 6-hydroxycyclohexene-1-carboxylate, the latter available from glutaraldehyde and the Emmons-Wadsworth-Horner phosphate reagent. This intermediate requires only two steps to convert to (-)-galanthamine. Using a Heck vinylation, we found that the fourth ring of codeine/morphine is formed. The final ring formation involves a novel visible light-promoted hydroamination. Thus, six steps are required to convert the pivotal tricyclic intermediate into codeine, which has been demethylated in high yield to morphine.

Analgesics, Opioid↗
PubMed1977

A rapid, high-yield conversion of codeine to morphine.

Brief treatment of codeine (1) in chloroform with boron tribromide has consiste-tly given morphine (2) in 90-91% yield after a simple isolation procedure. The yield and simplicity of operation in this method are vastly superior to those previously reported for this transformation.

Boron Compounds↗
PubMed1994

Double-blind comparison of an acetaminophen 400 mg-codeine 25 mg combination versus aspirin 1000 mg and placebo in acute migraine attack.

The purpose of this study was to compare the efficacy and tolerance of a single dose of the acetaminophen 400 mg-codeine 25 mg combination (ACC) aspirin 1000 mg (A) and a placebo (P) for the treatment of acute migraine attack. The study design was randomized, multicentre, double-blind and double dummy with cross-over on three periods. Of the 198 patients who had three attacks 29.8%, 52.3% and 49.7% had recorded the complete or almost complete disappearance of the pain at 2 h after P, A and ACC respectively. When compared with the placebo, the difference was significant for the A and ACC. When complete disappearance of pain at 2 h was used as a criterion, no significant difference was observed. These results enabled the sensitivity of the evaluation criteria suggested for clinical trials of migraine attack to be discussed.

Acetaminophen↗
PubMed1998

Tenoxicam and paracetamol-codeine combination after oral surgery: a prospective, randomized, double-blind, placebo-controlled study.

We studied 90 adults undergoing surgical removal of at least both lower third molar teeth as day cases under standardized general anaesthesia. Patients were allocated randomly (with stratification for surgeon) to receive tenoxicam 40 mg, tenoxicam 20 mg or placebo i.v. at induction of anaesthesia and orally (effervescent tablets) with food on each of the subsequent 2 days. Panadeine (paracetamol 500 mg-codeine 8 mg) was given before operation and was available as needed for pain thereafter, to a limit of two tablets every 4 h. Nefopam i.v. was also available. Efficacy variables and adverse reactions were assessed over 6 days. Over the 6-day period, patients who received tenoxicam reported less pain on rest (area under the curve; P < 0.05) and less disturbance in sleep (P < 0.01) even though they used fewer Panadeine tablets (P < 0.05). Differences between tenoxicam 40 mg and 20 mg were not significant. There was no significant difference in nefopam requirements or side effects, and no adverse event attributable to the study medication.

Acetaminophen↗
PubMedDate not supplied

Simultaneous determination of monoacetylmorphine, morphine, codeine, and other opiates by GC/MS.

A GC/MS method for the simultaneous determination of morphine, codeine, and O-6-monoacetylmorphine as well as other semisynthetic opiates in urine is described. The method employs 2H6-acetic anhydride to acetylate free hydroxyl groups on all of the opiates. As a result, the same hydrolysis and extraction procedure is used for all analytes. Quantitation is achieved using gas chromatography/mass spectrometry in the electron impact mode and with selected ion monitoring of the three most characteristic ions for each analyte. Ratios of these three ions are used for verifying identity while the molecular ions are used for quantitation. The detection limit for all analytes is less than 10 ng/mL.

Codeine↗
PubMedDate not supplied

Evaluation of analytical procedures for urinary codeine and morphine measurements.

Different analytical procedures for quantitation of total morphine and codeine in urine were evaluated. Hydrolysis of urine with hydrochloric acid and four different enzymes was compared. In order to effect complete hydrolysis of glucuronide conjugates, hydrolysis with 6.5M HCl containing bisulphite and heating at 100 degrees C for 20 min was required. Results using this hydrolysis procedure agreed well with results from direct analysis of free and conjugated forms by liquid chromatography. Use of more dilute HCl but at a higher temperature was not sufficient. Some enzymatic procedures appeared to give effective hydrolysis with a higher variability, but these procedures were more time-consuming. There was a good quantitative agreement between FID gas chromatography and ion-trap gas chromatography/mass spectrometry. The validated analytical procedure was applied to authentic patient samples.

Chromatography, Gas↗
PubMedDate not supplied

Extraction of benzoylecgonine (cocaine metabolite) and opiates (codeine and morphine) from urine samples using the Zymark RapidTrace.

The Zymark RapidTrace automated solid-phase extraction system has been evaluated for use in the urine drug-testing laboratory. Methods for cocaine metabolite (benzoylecgonine) and opiates (codeine and morphine) are described and evaluated. The linearity, precision, accuracy, recovery, and carryover statistics of these analytical protocols are presented. The advantages of extraction using the RapidTrace instead of solid-phase extraction with the manual vacuum manifold or liquid-liquid extraction methods are described.

Cocaine↗
PubMed1998

An evaluation of the role of ROC plots in the prediction of heroin use from total codeine and total morphine concentrations in urine.

A diagnostic system to predict the presence of 6-acetylmorphine (6AM) in opiate-positive urines was recently proposed. A twofold criterion based on the total morphine concentration and the total codeine to total morphine concentration ratio was identified. Using relative operating characteristic (ROC) analysis, it was determined that the diagnostic system had a sensitivity of 92%, a specificity of 79%, and an overall accuracy of 73%. We applied similar decision criteria to a study population of 125 opiate-positive urines collected from criminal justice clients of a West Coast reference laboratory. ROC analysis on this population produced very different results: a sensitivity of 91%, a specificity of 49%, and an accuracy of 45%. These data illustrate the importance of choosing a representative study population without any selection biases that may compromise the validity of the accuracy measure. The ROC plot is an important tool for assessing a clinical test's performance, but in order for toxicologists and Medical Review Officers to benefit from the diagnostic test results, they must also know the predictive value (based on test accuracy and the prevalence of heroin use) of the test results. They need to know how well the test predicts the presence of 6AM, and therefore, the illicit use of heroin, in the population of interest whether it be workplace, criminal justice, hospital emergency department clients, or a combination of all populations.

Cocaine-Related Disorders↗
PubMedDate not supplied

In vivo formation of codeinone-glutathione adduct: isolation and identification of a new metabolite in the bile of codeine-treated guinea pig.

Codeinone-glutathione adduct (CO-GSH) in the bile of guinea pigs given a subcutaneous injection of codeine was isolated and identified. Synthesized authentic CO-GSH was characterized by the mass and nuclear magnetic resonance spectra and used as the standard sample. The metabolite was isolated by preparative high-performance liquid chromatography on a C18 column. The fractions containing the conjugated metabolite were purified using Sep-Pak C18 cartridges. For further purification of the metabolite CO-GSH, a Radial Pak CN column was used. Structure assignment of the metabolite was then performed by fast-atom-bombardment mass spectrometry and 500 MHz Fourier-transform-NMR spectrometric analysis and identified as S-[4,5-epoxy-3-methoxy-17-methyl-6-oxomorphinan-(8S)-yl] glutathione.

Animals↗
PubMed2002

The simultaneous determination of codeine, morphine, hydrocodone, hydromorphone, 6-acetylmorphine, and oxycodone in hair and oral fluid.

Recently, the abuse of prescription opiates as alternatives to heroin has become a national concern. The determination of a six-drug opiate panel, codeine, morphine, 6-acetylmorphine, hydrocodone, hydromorphone, and oxycodone, in hair and oral fluid using solid-phase extraction and capillary gas chromatography-mass spectrometry (GC-MS) is described. Oral fluid was obtained from the donor by insertion of absorptive collectors into the mouth. Hair was collected from the patient and powdered using stainless steel ball bearings in a mini bead-beater apparatus. Opiates present in the samples were extracted from a buffered, aqueous matrix using a solid-phase cartridge. The extracts were concentrated and the methoxime/BSTFA derivatives prepared in order to eliminate interference from the keto-opiates. The extracts were separated by GC-MS in electron impact mode. By utilizing methoxyamine, we were able to produce the methoxime derivatives required for single derivative production and chromatographically separate all six opiates. The routine analysis of these opiates in hair and oral fluid using GC-MS is described for the first time.

Codeine↗
PubMedDate not supplied

Urinary concentrations of morphine and codeine after consumption of poppy seeds.

A quantitative analysis of morphine and codeine in human urine was performed after oral intake of cakes containing commercially available poppy seeds in order to estimate the possibility of positive doping results. Therefore, eight products from different manufacturers (poppy seeds or baking mixtures) and origin were obtained and analyzed by gas chromatography-mass spectrometry for the presence of the alkaloids. One selected batch of poppy seeds was used as an ingredient in a typical cake and was the object of an excretion study with nine volunteers. After application, several urine specimens contained morphine with concentrations higher than 1 microg/mL, and peak values of approximately 10.0 microg/mL were detected. Because the International Olympic Committee set a cutoff limit for morphine at 1 microg/mL, high-performance athletes could possibly test positive in doping control after consumption of products containing poppy seeds.

Aged↗
PubMedDate not supplied

Monitoring saliva concentrations of methaqualone, codeine, secobarbital, diphenhydramine and diazepam after single oral doses.

A preliminary investigation was undertaken to determine the feasibility of monitoring saliva levels of drugs for forensic purposes. Single oral doses of the title compounds were administered to healthy volunteers. Plasma and saliva levels were measured and ratios calculated for all drugs except diazepam. Saliva/plasma ratios for methaqualone, diphenhydramine and secobarbital were all less than one and reasonably consistent between collection times and subjects. The saliva/plasma ratios for codeine were more variable, but always greater than one. Although more detailed investigation is necessary, saliva may be a useful medium for forensic monitoring of drug ingestion.

Administration, Oral↗
PubMedDate not supplied

Application of the combined use of fused silica capillary columns and NPD for the toxicological determination of codeine and ethylmorphine in a human overdose case.

The applicability of capillary gas chromatography to the toxicological analysis of extracts of human tissue samples was investigated for codeine and ethylmorphine in a case of drug overdose. After column extraction, the samples were injected onto a fused silica capillary column, using a direct injection technique. The nitrogen-phosphorus detector provided excellent stability and sensitivity without the need for extensive clean-up procedures.

Adult↗
PubMedDate not supplied

Simultaneous determination of codeine and morphine in urine and blood by HPLC.

A procedure is presented for the determination of nanogram quantities of codeine and morphine in biological specimens by HPLC. The quantitative method is based on hydrolysis of the urine samples followed by basic extraction of urine and blood with organic solvents. Separation by liquid chromatography is a reverse phase system on a Spherisorb-CN (5 micron) column with a mobile phase of 40% methanol and phosphate buffer, pH 6.8. The method separated the opiates for screening purposes and was used for confirmation of morphine detected by radioimmunoassay.

Chromatography, High Pressure Liquid↗
PubMed1984

Descriptive epidemiology of mortality in New Jersey due to combinations of codeine and glutethimide.

A review of records of the Toxicology Laboratory of the New Jersey State Medical Examiner's Office yielded a total of 36 deaths attributable to overdose of "hits," an oral combination of codeine and glutethimide, during 1980-1981. During the same period, 126 deaths due to heroin overdose and 46 deaths due to methadone overdose occurred. The majority of hits cases (77.8%) occurred in the Newark vicinity. Demographic features of persons who died of the three agents are presented, and some explanations are advanced for the unexpectedly high mortality due to the oral narcotic combination.

Adult↗
PubMed1996

An assessment of the routes of incorporation of opiates into beard hair after a single oral dose of codeine.

The time course of appearance of immunoreactive opiates was monitored in saliva, sweat, and beard hair in six healthy whites who were not opiate users after oral administration of 60 mg of codeine phosphate. The opiate concentration in saliva peaked within 30 min of drug administration and returned to near the predose level within 24 h. Ninety-one percent of the total secretion of opiates in sweat was collected by the skin-collection patch worn during the first 24 h after drug administration. Detectable material was also present in sweat patches on the following 2 days. Opiates were detected in extracts of alkali digests of beard hair in all subjects on the day after drug administration. Hair concentration peaked on day 3 after dosing and then decreased continuously until day 8. From day 8 until the end of the experiment on day 14, beard hair contained opiate concentrations significantly greater than the predose level. From comparison with cotinine pharmacokinetics, it is proposed that an early and the largest transfer of opiates into beard hair is through sweat. Transfer during hair growth is secondary and of comparable importance to a newly identified contribution of long duration that may involve transfer from storage depots within skin.

Adult↗
PubMed1989

The effects of octreotide, soy polysaccharide, codeine and loperamide on nutrient, fluid and electrolyte absorption in the short-bowel syndrome.

Four agents, which could delay intestinal transit, were tested in six short-bowel patients (jejunal length 30-120 cm) on long-term nutritional/electrolyte replacement therapy. Intestinal transit time of a liquid test meal and nutrient, water and sodium absorption were measured during a control study and with each test agent on separate days. Soy polysaccharide tended to increase transit time, but decreased the absorption of water, sodium and nutrients. Codeine phosphate and loperamide caused inconsistent and clinically unimportant changes. Octreotide, a long-acting analogue of somatostatin, delayed transit and increased water, sodium and calorie absorption from the meal. Octreotide appears to have the potential to reduce the need for electrolyte and nutritional supplements in patients with the short-bowel syndrome.

Codeine↗