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At least 19 recordsLinked to original sources
PubMed1992

Increase in thebaine content of Papaver bracteatum Lindl. after colchicine treatment of seeds. Annual fluctuations in thebaine level of individual plants.

From colchicine-treated seeds of Papaver bracteatum Lindl. some poppy plants were obtained that developed capsules richer in thebaine than the controls. The individual poppies were analyzed for capsule thebaine content annually for eight successive years, the results revealing significant year-to-year differences. One of the poppies, X7, (ca 5% thebaine) developed capsules consisting partly of polyploid tissue during the first and second year. This plant was propagated vegetatively to give a series (the X7 series) of new P. bracteatum plants. The capsule thebaine content of these individuals differed markedly the first two years, whereupon the alkaloid production decreased and appeared to level out and reach a value still clearly higher than the controls (mean values 2.3% and 1.3%, respectively). From seeds of four of the thebaine-rich poppies of the X7 series, four new series of P. bracteatum plants were obtained. The capsule thebaine level of these was significantly lower than that of the mother plants.

Colchicine↗
PubMed1986

Precursors of the mammalian synthesis of morphine: (+)-salutaridine and (-)-thebaine from (+)-6-demethylsalutaridine, and (-)-N-13CH3-thebaine from (-)-northebaine.

Standard samples of pure (+)-salutaridine and (-)-thebaine required to study the mammalian origin of morphine, were prepared from (+)-6-demethylsalutaridine by published procedures and were characterized by CD spectra and physical data. Reductive N-methylation of (-)-northebaine afforded (-)-thebaine, and when 13C-labeled formalin was used, (-)-thebaine with a 13C label on the N-methyl carbon atom resulted. The latter represents a model procedure to prepare ultimately N-14CH3-labeled (-)-thebaine and 14C-labeled congeners.

Animals↗
PubMed1977

Papaver bracteatum Lindley: thebaine content in relation to plant development.

Four thebaine-rich varieties of P. bracteatum have been grown in the open over two seasons and the thebaine distribution in aerial parts examined to determine the most suitable source material for commercial production. The leaves contained only 0-1 to 0-15%; the capsules 0-5 to 3-0% and the bled latex 28 to 53%. The maximum for the latter occurred about 3-4 weeks after petal opening and during the day, at about 15,00 h. A product 'bractium' prepared exactly as opium from P. somniferum contained up to 55% thebaine and calculations from the 1974 results gave theoretical yields up to 58 k of thebaine per hectare. However this is a very labour intensive method; furthermore bled latex only represents about 46% of the total thebaine of the capsule. In addition the pedicels contain significant amounts of thebaine, so that fruiting tops may be recommended as source material. In the capsule the thebaine content reaches a peak 3 to 4 weeks after petal opening and again two weeks later. At this fully ripe stage there is a theoretical yield of 50 kg per hectare. Two further advantages accrue from collection at this time: the ripe seeds can probably be used for similar purposes as poppy seed; and the pericarps at this stage contain no 'bound thebaine' (i;e., thebaine insoluble in MeOH; NH4OH but soluble in acetic acid--in unripe capsules bound thebaine represents 18 to 36% of the total thebaine). There is some evidence that, as this perennial plant increases in age, the capacity for thebaine production seems to continue increasing. Storage of raw material, even in ideal conditions, led to a loss of thebaine of 12 to 20% in one year.

Papaver↗
PubMed1997

The analysis of thebaine in urine for the detection of poppy seed consumption.

The consumption of poppy seeds in various foods may lead to a positive opiate result in urine subjected to testing for drugs of abuse. As a natural constituent of poppy seeds, thebaine was investigated as a possible marker for poppy seed consumption. Poppy seeds were examined for opiate content by gas chromatography-ion trap mass spectrometry (GC-MS) after extraction with methanol. Urine samples spiked with thebaine and urine from subjects given 11 g of poppy seeds were tested for the presence of thebaine, codeine, and morphine. Street heroin, one morphine and one codeine tablet, and urine from individuals who had used heroin were also examined for thebaine. Urine specimens were screened by enzyme immunoassay (EMIT) and confirmed for thebaine by GC-MS using a solid-phase extraction method. The GC-MS assay showed a linear response over a range of 1-100 ng/mL and a limit of detection of 0.5 ng/mL. Thebaine was detectable in the urine of poppy seed eaters in concentrations ranging from 2 to 81 ng/mL. Because thebaine was absent in powdered drugs and the urine of true opiate drug users, thebaine is proposed as a direct marker for poppy seed use.

Codeine↗
PubMed1977

Thebaine content of selections of Papaver bracteatum Lindl. at different ages.

Approximately 200 accessions of Papaver species were evaluated for identification as P. bracteatum Lindl. and for thebaine content. Fifteen authentic P. bracteatum accessions were selected on the basis of chromosome count. Statistical analyses of variation in alkaloid content were made for these accessions. Four of the 15 warranted further study based on the vigor of the plant and the total thebaine present in the tissue. Significant variability in thebaine content was found in wild strains of P. bracteatum, thus requiring genetic selection studies. The data showed that total yield potential of thebain should be considered in selecting P. bracteatum strains for commercial growth rather than concentrating on strains that produce the highest thebaine concentrations. A method for the quantitative estimation of thebaine from P. bracteatum is presented.

Papaver↗
PubMed1981

Behavioral effects of thebaine in the rhesus monkey.

Three experiments were conducted with rhesus monkeys to assess some behavioral effects of the opium alkaloid, thebaine, in relation to its dependence liability. The concurrent intramuscular administration of naloxone did not antagonize the rate-decreasing effects of thebaine on a fixed-ratio (FR) schedule of food-reinforced responding. Animals trained to self-administer codeine (0.3 mg/kg/inj) on an FR 30 schedule did not self-administer thebaine (0.003-1.0 mg/kg/inj) at rates comparable to these of codeine. Rates were minimally above those of saline at 0.3 mg/kg inj. Monkeys given 23 hrs/day continuous access to 1.0 mg/kg/inj thebaine did, however, self-administer the drug at rates significantly higher than those maintained by saline, but not as high as those supported by 2.0 mg/kg/inj codeine. Two animals self-administering thebaine did not show any signs of withdrawal when injected with 0.1-1.0 mg/kg of naloxone or when saline was substituted for thebaine. A third monkey showed a severe reaction leading to death following an injection of 1.0 mg/kg naloxone.

Animals↗
PubMed1999

Stereoselective mu- and delta-opioid receptor-related antinociception and binding with (+)-thebaine.

In vivo and in vitro binding studies with natural thebaine and its enantiomer, (+)-thebaine were conducted to elucidate further their interactions with the opioid system. (-)-Thebaine a key intermediate in the biosynthesis of morphine in the poppy plant (Papaver somniferum) and in mammalian tissue, was poorly effective antinociceptively in mice at doses to 30 mg/kg. Its principal behavioral manifestation was lethal convulsions. Naltrindole, at doses of 1 and 10 mg/kg did not block either the convulsions or lethal effects, suggesting that the delta-opioid receptor system was not involved in this action. Surprisingly, the dextrorotatory isomer exhibited significant antinociceptive activity in the tail-flick [ED50 = 8.9 (3.4-22.1) mg/kg], hot-plate [ED50 = 22.9 (10.9-48.1) mg/kg] and phenylquinone [ED50) = 1.9 (1.6-9.5) mg/kg] assays. Studies with opioid receptor-subtype antagonists, beta-funaltrexamine, nor-binaltorphimine and naltrindole, indicated that antinociception was associated with mu- and delta-opioid receptors. Results of displacement experiments supported the in vivo data. Significant competition for [3H]diprenorphine binding with both isomers for cloned mu- and delta-opioid receptors was observed. However, (-)-thebaine was more effective at the delta-opioid receptor (Ki = 1.02+/-0.01 microM) whereas (+)-thebaine was more effective at the mu-opioid receptor ( Ki = 2.75+/-0.01 microM). Opioid-induced antinociception associated with unnatural thebaine raises the possibility of additional mu- and delta-opioid receptor sites.

Analgesics↗
PubMed1991

Thebaine O-demethylation to oripavine: genetic differences between two rat strains.

1. Codeine O-demethylation to morphine is mediated by cytochrome P450 IID1 (rat), or P450 IID6 (man), and exhibits genetic polymorphism. Thebaine is a precursor in the formation of endogenous morphine and codeine in man, being O-demethylated to oripavine. 2. The objective of the present study was to ascertain whether the O-demethylation of thebaine to oripavine was mediated by cytochrome P450 IID1 in rat liver microsomes. 3. Thebaine O-demethylation showed strain differences in female Sprague-Dawley (SD) and female Dark-Agouti (DA) rats, which serve as a model for the human debrisoquine/sparteine metabolism phenotypes. 4. The total intrinsic clearance of thebaine to oripavine was high (19.7 ml/h per mg protein) in SD rats, indicating that oripavine is a major metabolite of thebaine. A 3-fold lower intrinsic clearance was observed in DA rats (6.7 ml/h per mg protein). 5. Thebaine O-demethylation was inhibited by quinine and known substrates of cytochrome P450 IID1/P450 IID6, supporting the major involvement of cytochrome P450 IID1 in oripavine formation in rats.

Animals↗
PubMedDate not supplied

Thebaine variations between germplasm sources within one collection of Papaver bracteatum Lindl.

Plants of Papaver bracteatum Lindl. derived from different germplasm sources within one Iranian collection were grown for 18 and 37 weeks in the greenhouse and controlled environment chambers. Gas-chromatographic analyses showed significant differences between thebaine concentrations of root tissue for 18-week-old plants, but not for 37-week-old plants. The two age groups did not differ in thebaine yield per unit of dry weight of root tissue. However, due to more profuse root growth, the total yield of thebaine from roots of the older plants was about four times that of the younger plants. Shoot thebaine concentrations differed significantly for 18- and 37-week-old plants. The over-all mean thebaine concentration for shoots of older plants was nearly twice that of younger plants. The variation in thebaine concentrations in these plants suggested genetic differences between the germplasm sources. Thus, domestication of P. bracteatum will require selection of germplasm from within and between collections, for plants of the greatest economic potential.

Iran↗
PubMed1980

Recovery of thebaine and cryptopine from Indian opium.

The thebaine content of the opium collected in the Madhya Pradesh region of India has been estimated and reported to range from 1.5 to 2.0 per cent. A technological process for the recovery of thebaine from the mother liquor remaining after the separation of natural codeine in the Government Opium and Alkaloid Works, Neemuch, has been developed in the laboratory and stepped up to an industrial scale. A method for the recovery to thebaine from the waste slaked-lime residues obtained from crude alkaloid cake mother liquor in the Government Opium and Alkaloid Works at Ghazipur has been worked out and the technical details of the process described. The recovery of thebaine would help to increase the production of codeine, and thebaine can also be used as a raw material for the manufacture of other drugs. Cryptopine has also been recovered from the mother liquor after the separation of thebaine.

Alkaloids↗