A rapid, high-yield conversion of codeine to morphine
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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.Urinary total morphine: total codeine ratios were studied in two groups of people. Group A consisted of 76 subjects receiving three different medicinal preparations containing morphine or codeine, while Group B consisted of 33 drug abusers detected at urinary mass screening. Distinct differences in these ratios were observed. In Group A, total morphine: codeine ratios of 1:2.6 and below were obtained for subjects consuming either Tablet Codeine Co or Syrup Phensedyl. Subjects consuming Kaolin et Morphine mixture did not excrete any codeine in the urine. In Group B, total morphine: total codeine ratios of 1.9:1 and above were obtained. In addition all subjects in Group B excreted both morphine and codeine. The clear separation of the morphine: codeine ratios makes this a possible index to differentiate between these groups.
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Urinary levels of morphine and codeine were studied in two groups of people: Group A--urine samples of 76 subjects receiving three different medicinal preparations containing morphine or codeine. Group B--urine samples of 67 drug abusers detected at urinary mass screening. Distinct differences in these levels were observed. In Group A, UPPER 99% Confidence limits of morphine concentrations of 2.56 microgram/ml, 2.40 microgram/ml and 2.29 microgram/ml were reached after consumption of prescribed doses of Syrup Phensedyl, Tablet Codeine Co and Kaolin et Morphine mixture respectively. In Group B, the LOWER 99% Confidence limit of morphine concentration was 3 microgram/ml. In contrast, the codeine levels obtained for both groups were similar. The clear separation of the ranges of morphine values for the two groups shows that the urinary morphine level forms a reliable index for the differentiation between these two groups.
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Introduction/Objective. Heroin is metabolized to 6-monoacetylmorphine (6-MAM) and morphine. The objective of this study is to examine 6-MAM, morphine, and codeine relationships in order to distinguish deaths related to heroin consumption from deaths related to morphine and/or codeine consumption. Methods. The autopsy blood and urine samples from 45 opioid drug addicts were examined. Gas chromatography/mass spectrometry was applied to evaluate morphine, 6-MAM, and codeine. Two groups were formed: 6-MAM-positive (n = 35) and 6-MAM-negative (n = 10). Results. Compared to the 6-MAM-negative group, blood morphine levels were higher in the 6-MAMpositive group (p = 0.022), while blood codeine levels were similar (p = 0.575). In the 6-MAM-negative group, the blood morphine/codeine ratio was 8.3, and it was 4.3 in the 6-MAM-positive group. There was no difference between the groups regarding urine morphine levels (p = 0.859). The urine morphine/ codeine ratio was 6.2 in the 6-MAM-negative group, whilst it was 32.2 in the 6-MAM-positive group. In the blood samples, morphine and codeine concentrations were significantly correlated (r = 0.607; p = 0.006). In urine samples, correlations between morphine and codeine (r = 0.766; p < 0.001), morphine and 6-MAM (r = 0.650; p < 0.001), as well as codeine and 6-MAM (r = 0.620; p < 0.001), were also significant. Conclusion. Analyses of 6-MAM and morphine/codeine ratio in blood and urine autopsy samples may be used as diagnostic tools to distinguish deaths related to the consumption of different opioid drugs.
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Opiate
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The urinary excretion patterns of morphine and codeine in a number of individuals following consumption of morphine-based narcotic drugs have been studied. From the data collected the relative amounts of codeine and morphine in urine specimens were compared and certain trends, consistencies and irregularities were revealed. To a certain extent, the ratio of the proportion of codeine to morphine excretion in urine may be used to determine the nature of the drugs consumed. This correlation is useful in the interpretation of the results of urine analysis which is the basis of effective control and rehabilitation of drug addiction.
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After the ingestion of three poppy-seed bagels, the following codeine and morphine concentrations were determined in the urine: 214 ng/mL codeine and 2797 ng/mL morphine at 3 h, and 16 ng/mL codeine and 676 ng/mL morphine at 22 h. This work indicates that a positive finding of codeine or morphine in the urine of an individual does not necessarily indicate heroin, morphine, or codeine use.
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After administration of high-dose codeine we found that in two cases 20-40% of the total morphine-equivalents in the 24-hour urine sample were free morphine. After another 24 hours the proportion of free morphine was up to 70% and after roughly 96 hours even went up to 96%. Although 10% of the administered codeine was eliminated as morphine. In contrast to the values reported in literature we found that even with codeine/morphine ratios greater than 0.5 and morphine concentrations of up to 2000 ng/ml urine one cannot naturally conclude that morphine/diamorphine has been consumed. The short half-life of codeine in serum was 2-4 hours, the final half-life was 9-11 hours. In urine we found a short half-life of 1-6 hours as well as a long half-life of 7-12 hours. When diazepam was administered simultaneously with codeine the expected half-life in serum was up to 1.5 times and in urine 2.5 times. The codeine/morphine ratios were hardly affected so far as evidence goes which they give of preceding drug-intake.
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Endogenous codeine and morphine were identified in rat brain by immunological determination following HPLC. To demonstrate occurrence of a biosynthetic pathway to morphine in mammals similar to that used by the poppy plant, (+)-salutaridine, (-)-thebaine, and (-)-codeine were administered to rats intravenously. These compounds, which are intermediates in the synthesis of morphine in Papaver somniferum, caused a marked increase in the codeine and morphine levels in rat tissues. This provides evidence for a biosynthetic pathway to morphine in mammalians.
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The opioids codeine and morphine have legitimate uses in managing chronic pain conditions, but they are frequently abused. Patients prescribed opioids submit urine samples for medication compliance monitoring, and the interpretation of the results is complex. The purpose of this study was to evaluate the percentage of codeine- and morphine-positive urine drug tests that result from morphine use only, with the positive codeine result arising from low levels of codeine present in pharmaceutical formulations of morphine. This study included 80 urine samples which tested positive for codeine and morphine after pre-analytical hydrolysis and analysis by gas chromatography-mass spectrometry. Quantitative results were correlated with patient prescription information and immunoassay results to classify patients into one of four categories: heroin users (50%), codeine users (34%), codeine and morphine users (5%), and morphine users (11%). The percentage of codeine-positive resulting from morphine use was higher than previous estimates. Urine from patients prescribed morphine only was found to contain codeine at <1% of the morphine concentration, a ratio that was also observed in patients who used heroin. Careful analysis of urine drug testing results, including assessing the ratio of codeine to morphine (C/M), can help providers determine if patients are compliant with their pain management regimens.
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