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PubMed2002

A rapid GC-MS method for the determination of dihydrocodeine, codeine, norcodeine, morphine, normorphine and 6-MAM in urine.

The presence of the heroin metabolite 6-monoacetylmorphine (6-MAM) in urine is used to definitively identify recent heroin abuse. A rapid and sensitive GC-MS method for the simultaneous analysis of codeine, norcodeine, morphine, normorphine and 6-MAM in urine was developed and successfully applied to the analysis of 321 'heroin-positive' urine specimens from individual subjects (identified by the presence of 6-MAM), to provide quantitative urinary opiate excretion data for heroin abusers. The cohort analysed was composed of 238 males (age range 16-53 years) and 83 females (age range 16-50 years). The concentrations of free 6-MAM, morphine and codeine determined in these 321 specimens ranged between 103-246,312, 129-193,600 and 103-519,000 microg/l, respectively. Free norcodeine and normorphine concentrations were found to range between 143-50,200 and 205-149,700 microg/l, respectively. A statistically significant relationship was determined between the subject age and the 6-MAM concentration, possibly indicating opiate tolerance in these individuals.

Adolescent↗

PubMed2001

Simultaneous determination of codeine and ethyl morphine HCL in tablet formulations using LC.

A reverse phase high performance liquid chromatography (HPLC) method was developed for the simultaneous determination of codeine (methyl morphine) and dionin (ethyl morphine hydrochloride) in antitussive analgesic tablet formulations. A C(18) column and methanol-water (1:2) mixture mobile phase (pH 3.0) were used. Spectrophotometric detection was carried out at 210 nm. The total elution time was shorter than 7 min. This method was found to be quite precise and reproducible. This proposed method was successfully applied to the determination of codeine and ethyl morphine hydrochloride in tablets produced by the Turkish Army Drug Factory.

Chromatography, High Pressure Liquid↗

PubMed1998

TLC-UV densitometric and GC-MSD methods for simultaneous quantification of morphine and codeine in poppy capsules.

Thin-layer chromatographic (TLC)-UV densitometric and gas-chromatographic-mass spectrometric detection (GC-MSD) methods were developed for simultaneous quantification of morphine and codeine in poppy capsules (Papaver somniferum). Morphine and codeine were isolated by extraction with chloroform: isopropanol (3:1, v/v) at pH = 8.5 and by solid-phase extraction on Snap-Cap cartridges at pH = 8.5. The TLC-UV densitometric quantification was performed by external standard method on silica gel plates using ethyl acetate: toluene: methanol: ammonia (68:17:10:5, v/v) as developing solvent and UV detection at 275 nm. For the GC-MSD analysis, the drugs were derivatized with acetic anhydride: pyridine (1:1, v/v) and separated on a 30 m HP5 capillary column. The quantification was performed using nalorphine as internal standard.

Analgesics, Opioid↗

PubMed1986

Analgesia following arthroscopic surgery: comparison of diflunisal and acetaminophen with codeine.

In this study, 40 postarthroscopy patients were treated with either diflunisal or acetaminophen with codeine to control postoperative pain. In comparing these two drugs, better known as Dolobid and Tylenol #3, the results were comparable, though acetaminophen with codeine seemed to have a more rapid onset of action. Diflunisal provided better continuity of analgesia and less frequent dosing.

Acetaminophen↗

PubMed2000

Transdermal fentanyl in opioid-naive cancer pain patients: an open trial using transdermal fentanyl for the treatment of chronic cancer pain in opioid-naive patients and a group using codeine.

To treat cancer pain, physicians often decide to jump directly from step 1 of the World Health Organization (WHO) analgesic ladder to step 3. The use of transdermal fentanyl in patients with cancer pain who had either used no opioid before, or only codeine, is evaluated in the present trial. Both opioid-naive (N = 14) and codeine-using (N = 14) patients started with transdermal fentanyl in the lowest available delivery rate (25 microg/hr). Immediate-release oral morphine was present as "rescue" medication. Transdermal fentanyl provided good to excellent pain relief in the majority (68%) of these patients. During the study, 5 patients continued with 25 microg/hr, and the others used a higher dose. Clinically relevant respiratory depression was not observed. The common side effects of opioids were found; constipation was mentioned by 3 patients (11%). Transdermal fentanyl appeared a safe analgesic in these opioid-naive cancer pain patients. In this study, WHO step 2 could be skipped without untoward complications.

Administration, Cutaneous↗

PubMed2006

Optimized LC/MS/MS analysis of morphine and codeine in poppy seed and evaluation of their fate during food processing as a basis for risk analysis.

The opiate alkaloids present in poppy seed intended for use in food recently have raised major concerns. An efficient method for routine analysis of morphine and codeine using liquid chromatography in combination with tandem mass spectrometry on a triple quadrupole instrument (LC/MS/MS) was therefore developed. The optimal sample preparation was found to be cold extraction of 10 g of unground poppy seed with 30 mL of methanol containing 0.1% acetic acid for 60 min shaken at 250 rpm. The fate of morphine during food processing was also studied. All experiments led to a significant reduction of morphine and codeine. For poppy cake only 16-50% of the morphine was recovered, and in poppy buns at the highest temperature (220 degrees C) only 3% of the original morphine content was found. Ground poppy seed showed significantly lower recoveries than untreated seed. Morphine elimination during food processing has to be taken into account in the current discussion about its maximum limits in poppy seed.

Chromatography, High Pressure Liquid↗

PubMed1981

Efficient synthesis of 14-hydroxymorphinans from codeine.

Codeine is converted to 7,8-dihydro-14-hydroxynorcodeinone (noroxycodone) in six steps and 52% overall yield of the noroxymorphone in seven steps and 43% overall yield. N-Demethylation and oxidation of codeine afford N-(ethoxycarbonyl)norcodeinone, which is converted to its dienol acetate derivative and oxidized with singlet oxygen to give N-(ethoxycarbonyl)-14-hydroxynorcodeinone in the key step. Hydrogenation of the latter affords N-(ethoxycarbonyl)noroxycodone, which upon acid hydrolysis yields noroxycodone. Alternatively, O-demethylation of N-(ethoxycarbonyl)noroxycodone with boron tribromide and subsequent acid hydrolysis gives noroxymorphone. The results of the singlet oxygen oxidation of the pyrrolidine dienamine derived from N-(ethoxycarbonyl)norcodeinone are also described.

Chemical Phenomena↗

PubMed1976

A practical synthesis of codeine from dihydrothebainone.

The conversion of dihydrothebainone to codeine or thebaine has been achieved in high yield. Bromination and dehydrobromination constructs the 4,5-oxide bridge to give 1-bromo- and 1,7-dibromodihydrocodeinone which yield dihydrocodeinone practically quantitatively after catalytic debromination. Ketalization and acid-catalyzed elimination of methanol give excellent yields of delta6-dihydrothebaine to which is added methyl hypobromite using N-bromoacetamide in methanol. The action of potassium tert-butoxide in Me2SO on the resulting 7-bromodihydrocodeinone dimethyl ketal gives codeinone dimethyl ketal selectivity at 60 degrees while at 120 degrees thebaine is the exclusive product. Hydrolysis to codeinone and borohydride reduction give codeine in 70% overall yield. The bromo intermediates in the formation of the 4,5-oxide bridge have been examined. 1,5beta, 7alpha-Tribromodihydrothebainone has been identified as the main product in the tribromination of dihydrothebainone.

Codeine↗

PubMed1976

Conversion of Thebaine to Codeine.

An improved conversion of thebaine to codeine has been developed. Oxymercuration of thebaine with mercuric acetate in refluxing methanol, followed by hydrolysis of the intermediate 7-acetomercurineopinone dimethyl ketal with 3 N acetic acid, or, alternatively, reduction of the organomercury compound with sodium borohydride and mild acid hydrolysis of the resulting neopinone dimethyl ketal, gives neopinone in 95-100% yields. Either acid- or alkali-catalyzed isomerization to codeinone leads to the equilibrium mixture consisting of codeinone-neopinone, 3:1. Complete conversion to codeinone in 85-90% yield results from treatment of neopinone with anhydrous hydrogen chloride or hydrogen bromide in ether-methylene chloride, followed by elimination of hydrogen halide from the intermediate 8-halodihydrocodeinone. The known borohydride reduction of codeinone then gives codeine in 85% overall yield from thebaine.

Codeine↗

PubMed2000

Safety, efficacy, and long-term results of a modified version of rapid opiate detoxification under general anaesthesia: a prospective study in methadone, heroin, codeine and morphine addicts.

BACKGROUND: In the present study a method of rapid opiate detoxification under general anaesthesia has been evaluated regarding the safety, the efficacy in preventing withdrawal symptoms, and the long-term results. In addition, it was investigated whether the profile and severity of withdrawal symptoms depend on the type of opiate abused (methadone, heroin, codeine, morphine). METHODS: Seventy-two opiate addicts were detoxified in an intensive care unit (ICU). Anaesthesia was induced and maintained using propofol infusion. Patients were endotracheally intubated. The opiate receptor antagonist naltrexon was administered into the stomach via a nasogastric tube. Withdrawal symptoms before and after the detoxification treatment were assessed using an objective and a subjective opiate withdrawal scale (OOWS, SOWS). After detoxification patients entered a long-term naltrexone maintenance programme as well as a supportive psychotherapy programme. Vital organ function was monitored using haemodynamic and respiratory parameters as well as body temperature. RESULTS: Organ function parameters were stable during the whole treatment in all patients and no anaesthetic complications were registered. Minor side effects such as bradycardia or hypotension were observed in 20 patients. Compared to patients with pre-existing heroin, codeine, or morphine abuse respectively, patients from the methadone maintenance programme had significantly higher (P<0.01) OOWS as well as SOWS values after the treatment. Twelve months after the detoxification 49 patients (68%) were abstinent from opiates whereas 17 patients had relapsed during the period of follow-up. Six patients were lost during follow-up. CONCLUSIONS: Rapid opiate detoxification under general anaesthesia is a safe and efficient method to suppress withdrawal symptoms. This treatment may be of benefit in patients who particularly suffer from severe withdrawal symptoms during detoxification and who have failed repeatedly to complete conventional withdrawal. Methadone patients have more withdrawal symptoms than other opiate addicts.

Adult↗

PubMed2001

The use of compound 48/80 and codeine phosphate as positive controls for intradermal skin testing in dogs.

The mast cell secretagogues compound 48/80 and codeine phosphate were evaluated as potential positive controls for intradermal skin testing in dogs. Wheal responses to both agents were compared with responses to histamine and saline in 11 normal dogs, and were strong and not significantly different from histamine responses in nine dogs (P < 0.01), and significantly weaker than histamine in two dogs (P < 0.05). Wheal responses to compound 48/80 (1 mg mL-1) were evaluated in 82 suspected atopic dogs and were similar to histamine in 79 dogs and markedly weaker than histamine in three dogs. Of nine confirmed atopic dogs with weak responses to injected allergens, seven had strong responses to compound 48/80, and eight had strong responses to histamine. Compound 48/80 and codeine phosphate appear unreliable positive controls for skin testing in normal dogs. Compound 48/80 (1 mg mL-1) may be a reliable positive control in atopic dogs but is a poor indicator of skin reactivity to allergens.

Animals↗

PubMed1991

[Codeine and dihydrocodeine as substitute and alternative drugs].

There has been an increasing tendency in West Germany since the beginning of the 60s to abuse codeine and dihydrocodeine-containing drugs as substitutes and alternative drugs. This paper will firstly look at this situation from an epidemiological point of view and summarize the chemical and pharmacological effects, the side effects and toxicology of both kinds of substances. On the basis of own case reports the importance of codeine and dihydrocodeine during the development of an addiction of polydrug addicts and opiate addicts has been revealed, analysed and discussed, also with a view to the legal aspects in connection with the issue of treatment by substitution of drug dependents.

Adult↗

PubMed1990

[The detection of codeine abuse by hair analysis].

For the purpose of assessing possible opiate dependence (question of culpability) toxicological tests (gas chromatography; mass-spectrometry) were performed on cuttings of hair of a 30-year-old man who had within a short period committed several punishable offences 8 months previously. It was thus possible to determine opiate intake over a period of time corresponding to the length of hair. About 20 micrograms/g codeine and up to 4 micrograms/g morphine were demonstrated, in addition also 30 micrograms/g bromazepam. These results proved that amounts exceeding therapeutic levels of bromazepam and codeine-containing drugs had been taken during the period in question.

Adult↗

PubMed1986

Morphine and codeine from mammalian brain.

Recently, we described the presence of six immunoreactive (ir) morphinans in bovine adrenal and hypothalamus and identified one as morphine [Goldstein, A., Barrett, R. W., James, I. F., Lowney, L. I., Weitz, C. J., Knipmeyer, L. L. & Rapaport, H. (1985) Proc. Natl. Acad. Sci. USA 82, 5203-5207]. We now report that ir morphinans corresponding to the previously reported peak 1 (morphine), peak 4, and peak 5 are consistently present in extracts of bovine hypothalamus and variably present in extracts of bovine adrenal and rat brain. We no longer detect the previously reported peaks 2, 3, or 6, and we have established that they were contamination artifacts. Peak 1 is coeluted with morphine in two distinct reversed-phase HPLC systems, as is peak 4 with codeine. We have purified peak 1 and peak 4 compounds from bovine hypothalamus and determined their identities by gas chromatography/mass spectrometry (GC/MS): peak 1 is confirmed to be morphine and peak 4 is codeine.

Adrenal Glands↗

PubMed2003

The separation of codeine from nonprescription combination analgesic products.

In the United Kingdom number of products containing codeine in combination with nonopioid analgesics are available from pharmacies for purchase without a prescription. These products may be abused and it has been reported that in order to avoid nonopioid toxicity, some users may attempt to separate the components of combination analgesics, by mixing the dosage form in water and passing it through a coffee filtration apparatus (coffee filters). The present research sought to test the ease of separation of products available in the United Kingdom. The results obtained indicated that separation was possible; however, the extent of separation was influenced by the volume of water used and the product chosen. Healthcare professionals must be aware that separation may be attempted by those wishing to abuse codeine; however, significant nonopioid toxicity could still arise in the abuser.

Analgesics↗

PubMedDate not supplied

Testing human hair for drugs of abuse. I. Individual dose and time profiles of morphine and codeine in plasma, saliva, urine, and beard compared to drug-induced effects on pupils and behavior.

The time course of appearance of morphine and codeine in beard after single dose administration in two human subjects was monitored by radioimmunoassay and confirmed by gas chromatography/mass spectrometry. Both morphine and codeine appeared in beard approximately 7-8 days after drug administration at a time when drug levels in urine, plasma, and saliva were not detectable and drug-induced effects had disappeared. Drug levels in beard appeared to be dose-related suggesting that hair analysis can provide evidence of time and degree of drug exposure.

Behavior↗

PubMedDate not supplied

A simplified procedure for the determination of free codeine, free morphine, and 6-acetylmorphine in urine.

A procedure for detection and quantification of free codeine, free morphine, and 6-acetylmorphine in urine is presented. The analytes were extracted at neutral pH by solid-phase extraction prior to derivatization to their trifluoroacetyl derivatives. The derivatized extracts were analyzed by gas chromatography/mass spectrometry in the electron impact mode. Confirmation of the analytes was accomplished by comparing the ion abundance ratios of the analytes to those of a previously analyzed standard. The qualitative ion abundance ratios were required to be within 20% of those of the standard for acceptance. Quantification was based on the tri-deuterated analogs of the analytes. Linearity was obtained in the range of 10 to 1000 ng/mL, with correlation coefficients of all analytes exceeding 0.999. Percent recoveries were 90% for codeine, 88% for morphine, and 85% for 6-acetylmorphine. No hydrolysis of 6-acetylmorphine occurs during the extraction procedure. The authors also studied the stability of 6-acetylmorphine at various storage conditions of pH, temperature, and chemical preservation. 6-Acetylmorphine was found to be stable for 12 weeks when stored at -17 degrees C.

Chemistry Techniques, Analytical↗

PubMedDate not supplied

GC-MS confirmation of codeine, morphine, 6-acetylmorphine, hydrocodone, hydromorphone, oxycodone, and oxymorphone in urine.

A procedure for the simultaneous confirmation of codeine, morphine, 6-acetylmorphine, hydrocodone, hydromorphone, oxycodone, and oxymorphone in urine specimens by gas chromatography-mass spectrometry (GC-MS) is described. After the addition of nalorphine and naltrexone as the two internal standards, the urine is hydrolyzed overnight with beta-glucuronidase from E. coli. The urine is adjusted to pH 9 and extracted with 8% trifluoroethanol in methylene dichloride. After evaporating the organic, the residue is sequentially derivatized with 2% methoxyamine in pyridine, then with propionic anhydride. The ketone groups on hydrocodone, hydromorphone, oxycodone, oxymorphone, and naltrexone are converted to their respective methoximes. Available hydroxyl groups on the O3 and O6 positions are converted to propionic esters. After a brief purification step, the extracts are analyzed by GC-MS using full scan electron impact ionization. Nalorphine is used as the internal standard for codeine, morphine, and 6-acetylmorphine; naltrexone is used as the internal standard for the 6-keto-opioids. The method is linear to 2000 ng/mL for the 6-keto-opioids and to 5000 ng/mL for the others. The limit of quantitation is 25 ng/mL in hydrolyzed urine. Day-to-day precision at 300 and 1500 ng/mL ranged between 6 and 10.9%. The coefficients of variation for 6-acetylmorphine were 12% at both 30 and 150 ng/mL. A list of 38 other basic drugs or metabolites detected by this method is tabulated.

Codeine↗