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1.
Analyst ; 143(21): 5127-5136, 2018 Oct 22.
Artigo em Inglês | MEDLINE | ID: mdl-30280166

RESUMO

A method has been developed for extracting poppy alkaloids from oily matrices, specifically lipid residues associated with archaeological ceramics. The protocol has been applied to fresh and artificially aged poppyseed oil and to residue from a Late Bronze Age Cypriot juglet in the collections of the British Museum. The juglet is of a type that has been linked with ancient trade in opium due to its poppy-head shape and wide distribution; it is a rare example of an intact vessel with contents sealed inside. Bulk analysis of the residue by GC-EI-MS and pyGC-EI-MS indicated a degraded plant oil and possible presence of papaverine. Analysis of the alkaloid extracts by HPLC-ESI-MS using both triple quadrupole and FTICR mass spectrometers detected the five primary opium alkaloids in fresh poppyseed oil and papaverine in most of the aged samples. Papaverine and thebaine were detected in the juglet residue, providing the first rigorous chemical evidence to support a link between this vessel type and opium, or at least poppies. The association of opium with oil raises new questions about the ancient purpose of the commodities within these vessels, and the low levels (ng g-1) of opiates detected in this unusually well-preserved residue shed doubt on the scope for their detection in more fragmentary ceramic remains (potsherds). Papaverine was found to exhibit challenging carryover behaviour in all the analytical methods used in this study. The phenomenon has not been reported before and should be considered in future analyses of this analyte in all application areas.


Assuntos
Cerâmica/análise , Ópio/análise , Papaverina/análise , Óleos Vegetais/análise , Extração em Fase Sólida/métodos , Tebaína/análise , Arqueologia/métodos , Cromatografia Líquida de Alta Pressão/métodos , Cromatografia Gasosa-Espectrometria de Massas/métodos , Limite de Detecção , Papaver/química , Espectrometria de Massas por Ionização por Electrospray/métodos
2.
J Forensic Sci ; 63(4): 1229-1235, 2018 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-28973785

RESUMO

Recently, medical examiners reported two cases of a 21-year-old male and 24-year-old male with high amounts of morphine in their blood at autopsy. It was suspected that the decedents ingested lethal amounts of morphine from home-brewed poppy seed tea. No studies to date have investigated opium alkaloid content extracted from poppy seeds by home-brewing methods. Various poppy seed products were purchased from online sources and extracted with four home-brewing methods representative of recipes found on drug user forums. Morphine, codeine, and thebaine were quantified in the tea extracts by liquid chromatography-tandem mass spectrometry using a validated analytical method. Morphine, codeine, and thebaine concentrations from seeds were <1-2788 mg/kg, <1-247.6 mg/kg, and <1-124 mg/kg, respectively. Alkaloid yield varied between extractions, but regardless of extraction conditions, lethal amounts of morphine can be rinsed from poppy seed coats by home-brewing methods.


Assuntos
Codeína/análise , Morfina/análise , Papaver , Sementes , Chá/química , Tebaína/análise , Cromatografia Líquida , Toxicologia Forense , Humanos , Masculino , Espectrometria de Massas em Tandem , Adulto Jovem
3.
J Chromatogr A ; 1511: 77-84, 2017 Aug 18.
Artigo em Inglês | MEDLINE | ID: mdl-28689582

RESUMO

The separation of a mixture containing five major opium alkaloids, namely morphine, codeine, thebaine, noscapine and papaverine has been investigated in hydrophilic interaction liquid chromatography (HILIC) mode using five different stationary phases: bare silica, zwitterion, aminopropyl, diol and cyanopropyl. In order to propose the appropriate column for separation and purification, retention behaviors of the five natural opioids have been studied on mentioned HILIC stationary phases. The mechanism of separation in diverse HILIC media, based on the formation of water-rich layer on surface of the HILIC stationary phases and the physicochemical properties of opium alkaloids, such as pKa (acidic pK) and the octanol-water distribution coefficient (log Do/w) are discussed. Chromatographic responses including modified limit of detection LODm, signal to noise ratio (S/N)m, and defined modified RSm have considered for suggestion of the suitable column for quantitative/qualitative and preparative purposes. According to the obtained results, diol stationary phase is best suited for analytical chromatography, whereas bare silica and zwitterionic stationary phases are appropriate for preparative applications.


Assuntos
Alcaloides/análise , Ópio/química , Cromatografia Líquida/métodos , Codeína/análise , Interações Hidrofóbicas e Hidrofílicas , Morfina/análise , Noscapina/análise , Papaverina/análise , Dióxido de Silício/química , Tebaína/análise
4.
J Nat Med ; 68(4): 677-85, 2014 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-24952707

RESUMO

In May 2011, numerous poppy plants closely resembling Papaver bracteatum Lindl., a type of narcotic plant that is illegal in Japan, were distributed directly from several large flower shops or through online shopping throughout Japan, including the Tokyo Metropolitan area. In order to better identify the narcotic plants, the relative nuclear DNA content at the vegetative stage was measured by flow cytometric (FCM) analysis in 3 closely-related species of the genus Papaver section Oxytona, namely P. orientale, P. pseudo-orientale, and P. bracteatum, based on the difference between the chromosome numbers of these species. The results showed that the nuclear DNA content differed between these 3 species, and that most of the commercially distributed plants examined in this study could be identified as P. bracteatum. The remaining plants were P. pseudo-orientale, a non-narcotic plant. In addition, the FCM results for the identification of P. bracteatum completely agreed with the results obtained by the morphological analysis, the inter-genic spacer sequence of rpl16-rpl14 (PS-ID sequence) of chloroplast DNA, and the presence of thebaine. These results clearly indicate the usefulness of FCM analysis for the identification of P. bracteatum plants, including when they are in their vegetative stage.


Assuntos
Citometria de Fluxo , Papaver/classificação , DNA de Cloroplastos/química , Flores/química , Japão , Entorpecentes/análise , Papaver/anatomia & histologia , Papaver/química , Papaver/genética , Tebaína/análise
5.
Drug Test Anal ; 6(3): 194-201, 2014 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-24339374

RESUMO

A major toxicological challenge is distinguishing whether morphine in urine, in the absence of 6-monoacetylmorphine (6-MAM), originates from 'street' heroin use or poppy seed ingestion. Manufacturing byproducts from the synthesis of illicit heroin include those that originate from the reaction of acetic anhydride with the alkaloid impurity, thebaine, which undergoes skeletal rearrangement, resulting in compounds with a 2-(N-methylacetamido)ethyl side-chain. The hypothesis that the tertiary amide in this side-chain is resistant to endogenous hydrolysis was supported from in-vitro experiments; a glucuronide metabolite (designated 'ATM4G') was identified that may be used as a marker of 'street' heroin administration. Liquid chromatography-tandem mass spectrometry (LC-MS/MS) analysis for this metabolite was then performed on selected urine specimens from 22 known heroin users, these being negative on routine testing for 6-MAM by gas chromatography-mass spectrometry (GC-MS), using the generally applied reporting threshold of 10 ng/mL, but positive for the presence of morphine. Peaks corresponding to the retention time for the metabolite marker were clearly observed for 16 of the 22 samples, with variations of the ratios of its three dependent ions being within ± 30% of that produced in vitro. Conversely, 6-MAM was detected in only 3 samples, but at concentrations <1 ng/mL. Such a high frequency for the presence of the metabolite marker in urine, in the absence of 6-MAM, is noteworthy and suggests that detection of this metabolite may offer an important advance in forensic toxicology, allowing the development of a new and more definitive test for heroin abuse and thus a potential solution to the so-called 'poppy seed defense'.


Assuntos
Heroína/urina , Derivados da Morfina/urina , Papaver , Detecção do Abuso de Substâncias/métodos , Tebaína/urina , Acetilação , Adulto , Cromatografia Líquida/métodos , Cromatografia Gasosa-Espectrometria de Massas , Heroína/análise , Heroína/metabolismo , Humanos , Masculino , Pessoa de Meia-Idade , Derivados da Morfina/análise , Derivados da Morfina/metabolismo , Papaver/química , Sementes/química , Espectrometria de Massas em Tandem/métodos , Tebaína/análise , Tebaína/metabolismo
6.
Planta Med ; 78(12): 1395-8, 2012 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-22763738

RESUMO

In this paper, we report a case of misidentification of medicinal plants involving dried petals of Papaver rhoeas (red poppy) contaminated with Papaver bracteatum (scarlet poppy) petals. Preliminary TLC analysis indicated the presence of thebaine either in the fluid extracts or in the petals. It was therefore necessary to carry out an accurate botanic examination of the plant material, which revealed contamination of the red poppy petals with scarlet poppy petals. Moreover, to confirm the adulteration, we developed and validated an efficient, reversed-phase ion pair HPLC method for determination of the alkaloids specific for the Papaver species. Six petal batches and five commercial fluid extracts were analyzed. Only one petal batch from Iran contained thebaine and its analogue oripavine while the alkaloids typical for the Papaver bracteatum species were identified in all fluid extracts, meaning that they were all prepared with contaminated petals.


Assuntos
Flores/química , Papaver/química , Papaver/classificação , Extratos Vegetais/química , Tebaína/análogos & derivados , Tebaína/análise , Cromatografia Líquida de Alta Pressão/métodos , Cromatografia de Fase Reversa/métodos , Contaminação de Medicamentos , Europa (Continente) , Irã (Geográfico) , Especificidade da Espécie
7.
Artigo em Inglês | MEDLINE | ID: mdl-22165856

RESUMO

Poppy seed-containing foods are popular dishes in Hungary and some other Central European countries. The alkaloids of poppy are used in the production of medicines. Poppy seeds used as food may also contain considerable amounts of alkaloids, which raises the question of food safety. Morphine, codeine, thebaine and noscapine concentrations of poppy seed samples from the period 2001-2010 and consumption data from two Hungarian surveys, carried out in 2003 and 2009, were evaluated. Exposure calculations were made for morphine intake by both point estimate and probabilistic methods, and the uncertainty of the calculated values was estimated. The point estimate for the acute consumer exposure, calculated using the 97.5th percentiles of morphine concentration and of poppy seed consumption and taking into account the reduction of morphine content by processing, was 78.64 µg (kg bw)⁻¹ day⁻¹ for adults, and 116.90 µg (kg bw)⁻¹ day⁻¹ for children. Based on probabilistic estimations, the 97.5th and 99th percentile exposures ranged between 18.3-25.4 and 25.6-47.4 µg (kg bw)⁻¹ day⁻¹ for adults, and between 32.9 and 66.4 µg (kg bw)⁻¹ day⁻¹ for children, respectively. As a no observed effect level (NOEL) had not been established, the significance of exposure could not be assessed.


Assuntos
Dieta/efeitos adversos , Morfina/administração & dosagem , Morfina/análise , Entorpecentes/administração & dosagem , Entorpecentes/análise , Papaver/química , Sementes/química , Adulto , Criança , Codeína/análise , Dieta/etnologia , Dieta/tendências , Registros de Dieta , Feminino , Análise de Alimentos , Manipulação de Alimentos , Humanos , Hungria , Lactente , Masculino , Modelos Biológicos , Morfina/efeitos adversos , Entorpecentes/efeitos adversos , Noscapina/análise , Papaver/efeitos adversos , Medição de Risco/métodos , Sementes/efeitos adversos , Tebaína/análise
8.
Anal Chim Acta ; 701(2): 181-8, 2011 Sep 09.
Artigo em Inglês | MEDLINE | ID: mdl-21801886

RESUMO

Opium determination is of great importance from toxicological and pharmaceutical standpoints. In present work, electromembrane extraction (EME) coupled with high-performance liquid chromatography (HPLC) and ultraviolet (UV) detection was developed for determination of thebaine as a natural alkaloid, in different matrices containing water, urine, poppy capsule, street heroine, and codeine tablet. Thebaine migrated from 3 mL of sample solutions, through a thin layer of 2-nitrophenyl octyl ether (NPOE) immobilized in the pores of a porous hollow fiber, and into a 15 µL acidic aqueous acceptor solution present inside the lumen of the fiber. The variables of interest, such as chemical composition of the organic liquid membrane, stirring speed, extraction time and voltage, pH of donor and acceptor phases and salt effect in the EME process were optimized. Under optimal conditions, thebaine was effectively extracted from different matrices with recoveries in the range of 45-55%, which corresponded to preconcentration factors in the range of 90-110. Good linearity was achieved for calibration curves with a coefficient of estimation higher than 0.997. Detection limits and intra-day precision (n=3) were less than 15 µg L(-1) and 8.9%, respectively.


Assuntos
Líquidos Corporais/química , Cromatografia Líquida de Alta Pressão/métodos , Entorpecentes/química , Papaver/química , Tebaína/análise , Água/química , Cápsulas/química , Técnicas Eletroquímicas/métodos , Éteres/química , Concentração de Íons de Hidrogênio , Sais/química , Tebaína/isolamento & purificação
9.
Forensic Sci Int ; 204(1-3): 115-8, 2011 Jan 30.
Artigo em Inglês | MEDLINE | ID: mdl-20558018

RESUMO

Opium poppy products are often illegally used for both recreational and medicinal purposes. In order to demonstrate the ingestion of opium poppy substances, morphine, codeine and their metabolites have been identified. However, morphine and codeine also originate from the ingestion of therapeutic drugs. Therefore, thebaine, one of the main opium alkaloids, in hair was suggested as a marker for chronic use of illegal opium poppy substances in the present study. First, thebaine was included in the analyte list of our routine analytical method for the simultaneous quantification of codeine, morphine, norcodeine, normorphine and 6-acetylmorphine (6-AM) in hair, which was fully validated previously. Then, the incorporation of thebaine and other opiates into hair and the effect of hair pigmentation were examined using lean Zucker rats with both dark grey and white hair on the same body. Thebaine was also measured in hair samples from actual cases of opium poppy substance use. Consequently, thebaine in hair was demonstrated as a marker of chronic use of illegal opium poppy substances using an animal study and actual cases. Thebaine and other opiates were successfully measured in pigmented hair from rats that ingested raw opium suspension. Moreover, thebaine identified in hair excluded possibility of ingestion of pharmaceutical opiates in actual cases.


Assuntos
Cabelo/química , Entorpecentes/análise , Transtornos Relacionados ao Uso de Opioides/diagnóstico , Ópio/análise , Tebaína/análise , Adulto , Animais , Biomarcadores/análise , Feminino , Toxicologia Forense , Cromatografia Gasosa-Espectrometria de Massas , Humanos , Masculino , Pessoa de Meia-Idade , Papaver , Ratos , Ratos Zucker , Detecção do Abuso de Substâncias/métodos
10.
J Sep Sci ; 33(14): 2153-9, 2010 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-20552599

RESUMO

This study investigated the use of ultrasound-assisted extraction to improve the extraction efficiency of morphine, codeine and thebaine from the papaver plants. Extraction conditions such as type of solvent, temperature, duration, frequency and power level of ultrasonic were optimized and the influences of different parameters on resolution of alkaloids in CE were studied. The optimized condition for CE separation includes a sodium phosphate buffer (100 mM, pH 3.0) containing 5 mM alpha-CD. The optimized extraction conditions for ultrasound-assisted extraction was an extraction time of 1 h, an ultrasonic frequency of 60 kHz with water-methanol (80:20) at 40 degrees C as the extraction solvent. The LOD for alkaloids was found to be 0.1 microg/mL at a signal-to-noise ratio of 3:1. The RSDs for peak areas were in the range of 1.4-4.4%. The amounts of opium alkaloids (mg/100 g dried sample) in four Iranian papaver plants were found to be in the range of 7.8-8.7 (morphine), 5.5-9.5 (codeine) and 1.4-10.4 (thebaine). It should be emphasized that no cleanup of the filtered extract was required; hence, direct determination after extraction drastically simplifies the analytical process.


Assuntos
Codeína/análise , Ciclodextrinas/química , Eletroforese Capilar/métodos , Morfina/análise , Papaver/química , Tebaína/análise , Ultrassom , Tampões (Química) , Eletroforese Capilar/instrumentação , Concentração de Íons de Hidrogênio , Limite de Detecção , Extratos Vegetais/química , Solventes/química , Temperatura
11.
Artigo em Inglês | MEDLINE | ID: mdl-20042361

RESUMO

In this work, a batch chemiluminescence (CL) method has been proposed for the simultaneous determination of two structurally similar alkaloids, noscapine and thebaine. The method is based on the kinetic distinction of the CL reactions of noscapine and thebaine with Ru(bipy)(3)(2+) and Ce(IV) system in a sulfuric acid medium. The least squared support vector machine (LS-SVM) regression was applied for relating the concentrations of both compounds to their CL profiles. The parameters of the model consisting of sigma(2) and gamma were optimized by constructing LS-SVM models with all possible combinations of these two parameters to select the model with the minimum root mean squared error of cross validation (RMSECV) as the best. The parameters of this model were then selected as optimized values. Under the optimized experimental conditions for both compounds, the detection limits obtained using the LS-SVM regression were 0.08 and 0.1 micromo lL(-1) for noscapine and thebaine, respectively. The proposed method was utilized for the simultaneous determination of the compounds in pharmaceutical formulations and plasma samples with satisfactory results.


Assuntos
Cério/química , Noscapina/análise , Rubídio/química , Tebaína/análise , Luminescência , Modelos Estatísticos
12.
J Sep Sci ; 30(17): 3011-7, 2007 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-17960847

RESUMO

A method for the separation and determination of five major opium alkaloids (narcotine, papaverine, thebaine, codeine, and morphine) in pericarpium papaveris by pressurized CEC (pCEC) with monolithic column has been developed. Under the optimum condition, linear calibration ranges of narcotine, papaverine, thebaine, codeine, and morphine were obtained as 2-85, 2-85, 5-75, 10-65, and 10-65 microg/mL, respectively. LODs of these analytes were 1.5-6.0 microg/mL. The RSD (n=7) of the migration time and peak area were 1.94-5.24 and 4.05-8.21%, respectively. The proposed method was successfully applied to the analysis of pericarpium papaveris samples. Average recoveries of 79.0-95.9% at different fortified levels of alkaloids were achieved with RSD less than 4.6%. Meanwhile, the mechanism of the separation of the alkaloids on the monolithic column was also discussed. The result showed that the separation of alkaloids was mainly based on the mixed mode of hydrophilic interaction (HI) and cation exchange.


Assuntos
Eletrocromatografia Capilar/métodos , Codeína/análise , Morfina/análise , Noscapina/análise , Papaverina/análise , Tebaína/análise , Eletrocromatografia Capilar/instrumentação , Cátions/química , Troca Iônica , Conformação Molecular , Tamanho da Partícula , Pressão , Reprodutibilidade dos Testes , Sensibilidade e Especificidade , Estereoisomerismo , Propriedades de Superfície , Fatores de Tempo
13.
J Pharm Biomed Anal ; 43(3): 1164-8, 2007 Feb 19.
Artigo em Inglês | MEDLINE | ID: mdl-17097256

RESUMO

This paper describes the determination of opiate alkaloids (morphine, codeine, oripavine and thebaine) in industrial process liquors using capillary zone electrophoresis with UV-absorption detection at 214 nm. A study of cyclodextrin type and concentration revealed that the addition of 30 mM hydroxypropyl-beta-cyclodextrin to the electrolyte solution (100mM Tris adjusted to pH 2.8) was suitable to resolve the four analytes of interest. Typical analysis time was 12 min and the limit of detection for each alkaloid was 2.5 x 10(-6) M. The results for the proposed methodology were in good agreement with those of a conventional HPLC procedure. Under the same conditions, short-end injection was used to reduce the effective separation length from 41.5 to 8.5 cm, which allowed the determination of morphine and thebaine in process liquors within 2.5 min.


Assuntos
Alcaloides/análise , Analgésicos Opioides/análise , Eletrocromatografia Capilar , Cromatografia Líquida de Alta Pressão , Codeína/análise , Ciclodextrinas/análise , Indicadores e Reagentes , Morfina/análise , Solventes , Espectrofotometria Ultravioleta , Tebaína/análogos & derivados , Tebaína/análise
14.
J Chromatogr B Analyt Technol Biomed Life Sci ; 822(1-2): 137-45, 2005 Aug 05.
Artigo em Inglês | MEDLINE | ID: mdl-15993661

RESUMO

Opiates are some of the most widely prescribed drugs in America and are often abused. Demonstrating the presence or absence of opiate compounds in postmortem fluids and/or tissues derived from fatal civil aviation accidents can have serious legal consequences and may help determine the cause of impairment and/or death. However, the consumption of poppy seed products can result in a positive opiate drug test. We have developed a simple method for the simultaneous determination of eight opiate compounds from one extraction. These compounds are hydrocodone, dihydrocodeine, codeine, oxycodone, hydromorphone, 6-monoacetylmorphine, morphine, and thebaine. The inclusion of thebaine is notable as it is an indicator of poppy seed consumption and may help explain morphine/codeine positives in cases where no opiate use was indicated. This method incorporates a Zymark RapidTracetrade mark automated solid-phase extraction system, gas chromatography/mass spectrometry, and trimethyl silane (TMS) and oxime-TMS derivatives. The limits of detection ranged from 0.78 to 12.5 ng/mL. The linear dynamic range for most analytes was 6.25-1600 ng/mL. The extraction efficiencies ranged from 70 to 103%. We applied this method to eight separate aviation fatalities where opiate compounds had previously been detected.


Assuntos
Autopsia/métodos , Derivados da Morfina/análise , Entorpecentes/análise , Tebaína/análise , Autoanálise , Líquidos Corporais/química , Calibragem , Cromatografia Gasosa-Espectrometria de Massas/métodos , Toxicologia/métodos
15.
Artigo em Japonês | MEDLINE | ID: mdl-14740399

RESUMO

The effect of fertilizer on the yield and yield components of opium from Papaver somniferum L.cv.Ikkanshu were investigated from 1993 to 1995. The weight of opium per one capsule was tendency to increase in the order of peat moss > pulverized charcoal > compound fertilizer, but the differences among the results were not significant. Furthermore, no difference in the capsule weight per 100 m2 and the yields of opium and alkaloids per 100 m2 were detected. The significant difference was only observed when the data were compared among the weights and yields of different years. The difference among the yield of opium was mainly due to the weight of opium per one capsule. The weight of opium per one capsule showed a high correlation with capsule husk weight. The alkaloids contents in opium obtained with a different fertilizer application showed no difference. Morphine content at the first lancing was about 11%, and the value decreased with the order of lancing. On the contrary, the codeine and the thebaine content did not change during lancing and the value were 6-7% and 3%, respectively. The papaverine and the noscapine content decreased in the order of lancing.


Assuntos
Fertilizantes , Ópio/análise , Papaver/química , Codeína/análise , Morfina/análise , Noscapina/análise , Ópio/química , Papaver/crescimento & desenvolvimento , Papaverina/análise , Tebaína/análise , Fatores de Tempo
16.
Analyst ; 125(1): 91-5, 2000 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-10885066

RESUMO

A simple and robust capillary electrophoresis chemiluminescence detection system for the determination of morphine, oripavine and pseudomorphine is described, based upon the reaction of these analytes with acidic potassium permanganate in the presence of sodium polyphosphate. The reagent solution was contained in a quartz detection cell which also held both the capillary and the anode. The resultant chemiluminescence was monitored directly using a photomultiplier tube mounted flush against the base of the detection cell. To ensure that no migration of the permanganate anion occurred, the anode was placed at the detector end whilst the electroosmotic flow was reversed by the addition of hexadimethrine bromide (0.001% m/v) to the electrolyte. The three analytes were separated counter to the electroosmotic flow via their interaction with alpha-cyclodextrin. The methodology realised detection limits (3 x S/N) of 2.5 x 10(-7) M for both morphine and oripavine and 5 x 10(-7) M for pseudomorphine. The relative standard deviations of the migration times and the peak heights for the three analytes ranged from 0.6 up to 0.8% and from 1.5 up to 2.1%, respectively.


Assuntos
Morfina/análise , Entorpecentes/análise , Eletroforese Capilar , Medições Luminescentes , Morfina/química , Derivados da Morfina/análise , Derivados da Morfina/química , Entorpecentes/química , Tebaína/análogos & derivados , Tebaína/análise , Tebaína/química
17.
Forensic Sci Int ; 96(1): 29-38, 1998 Aug 31.
Artigo em Inglês | MEDLINE | ID: mdl-9800363

RESUMO

The universally accepted 300 ng/ml cut-off limit for opiate assays stated to be mandatory for all drug screening laboratories by the Substance Abuse and Mental Health Services Administration, has been questioned recently due to positive results being obtained following the ingestion of poppy seed containing food products. To establish the plausibility of the 'the poppy seed defence' the concentrations of codeine, norcodeine, morphine, normorphine and thebaine (a potential marker for seed ingestion) in several varieties of poppy seeds from different countries were quantified by GC-MS. The country of origin of the seed specimen analysed and the preparation of the seeds prior to their culinary use was found to influence the alkaloid concentration determined. The maximum morphine and codeine concentrations determined in the seeds were found to be 33.2 and 13.7 micrograms/g seed respectively. In addition, thebaine concentrations were found to vary with each seed sample analysed. Following the consumption of bread rolls (mean 0.76 g seed covering per roll) by four subjects, all urine specimens analysed produced negative results (using the Dade Bebring EMIT II opiate screening assay) with the exception of one subject (body weight 63.0 kg) who consumed two poppy seed rolls. In this subject opiate positive screening results were obtained for up to 6 h post ingestion with maximum urinary morphine and codeine concentrations of 832.0 ng/ml (@ 2-4 h post ingestion) and 47.9 ng/ml (@ 0-2 h post ingestion) respectively being achieved. Following the ingestion of poppy seed cake containing an average of 4.69 g of seed per slice by four individuals, opiate positive screening results were obtained for up to 24 h. In one subject (dose equivalent to 0.07 g poppy seed/kg body weight) maximum urinary morphine and codeine concentrations of 302.1 ng/ml (@ 0-2 h) and 83.8 ng/ml (@ 2-4 h) respectively were recorded. The elimination of thebaine was found to vary widely between individuals, therefore suggesting that its absence from a specimen is not necessarily indicative of opiate abuse. These findings demonstrate that the poppy seed defence could be used as an argument in medico-legal and employment medical cases. Great care should therefore be taken when interpreting the data produced when screening for opiates.


Assuntos
Entorpecentes/análise , Papaver/química , Plantas Medicinais , Sementes/química , Administração Oral , Adulto , Codeína/análogos & derivados , Codeína/análise , Codeína/urina , Análise de Alimentos/métodos , Cromatografia Gasosa-Espectrometria de Massas , Humanos , Masculino , Morfina/análise , Morfina/urina , Derivados da Morfina/análise , Derivados da Morfina/urina , Entorpecentes/urina , Tebaína/análise , Tebaína/urina
18.
Planta Med ; 62(6): 544-7, 1996 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-9000887

RESUMO

In addition to codeine and morphine, three more compounds: narcotine (noscapine), papaverine, and thebaine were found in Indian and Netherlands poppy seeds (Papaver somniferum L). The compounds were detected by a GC/MS technique and the identities were confirmed by comparing retention times and ion ratios with the known references. The concentrations of codeine, morphine, thebaine, papaverine, and narcotine were 44, 167, 41, 67, and 230 micrograms/g in Indian poppy seeds, and were 1.8, 39, 1.0, 0.17, 0.84 micrograms/g in Netherlands poppy seeds, respectively. Because these compounds may be urinary products after poppy seed consumption, the lowest detectable concentrations of codeine, morphine, thebaine, papaverine, and narcotine in urine are of interest and were found to be 4, 4, 5, 0.4, and 4 ng/ml, respectively. The detection of urinary narcotine, papaverine, or thebaine may be utilized to differentiate poppy seed consumption from illicit codeine, morphine, or heroin use.


Assuntos
Noscapina/análise , Papaver/química , Papaverina/análise , Plantas Medicinais , Tebaína/análise , Cromatografia Gasosa-Espectrometria de Massas , Humanos , Noscapina/urina , Papaverina/urina , Sementes/química , Detecção do Abuso de Substâncias , Tebaína/urina
19.
Biol Pharm Bull ; 16(10): 1051-3, 1993 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-8287039

RESUMO

Opium alkaloids (thebaine, codeine and morphine) have been conjugated with bovine serum albumin (BSA) to give individual antigen conjugates which are analyzed by matrix-assisted laser desorption/ionization (MALDI) mass spectrometry. It became clear that 9 molecules of thebaine were contained in a thebaine-BSA conjugate. Codeine and morphine contents in individual conjugates were determined to be 12 and 6 molecules, respectively.


Assuntos
Codeína/análise , Morfina/análise , Soroalbumina Bovina/análise , Tebaína/análise , Lasers , Espectrometria de Massas/métodos
20.
Proc Natl Acad Sci U S A ; 86(2): 716-9, 1989 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-2911601

RESUMO

The convulsant opiate thebaine, an intermediate of morphine biosynthesis, was purified from bovine brain to homogeneity by gel filtration and high-performance liquid chromatography (HPLC) monitored by a radioimmunoassay. The immunoreactive material behaved identically to standard thebaine in two HPLC systems and was confirmed to be thebaine by combined gas chromatography/mass spectrometry. To our knowledge, the presence of thebaine in mammalian tissue has not been demonstrated previously. Codeine and morphine were also found to exist in ovine brain. The presence of thebaine in ovine brain provides strong evidence that morphine and codeine, in various mammalian tissues, are of endogenous origin and actually biosynthesized from a precursor.


Assuntos
Química Encefálica , Tebaína/análise , Animais , Fenômenos Químicos , Química , Cromatografia em Gel , Cromatografia Líquida de Alta Pressão , Codeína/análise , Codeína/biossíntese , Cromatografia Gasosa-Espectrometria de Massas , Morfina/análise , Morfina/biossíntese , Radioimunoensaio , Ovinos
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