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PubMed1986

Separation and identification of illicit heroin samples by liquid chromatography using an alumina and C18 coupled column system and photodiode array detection.

The analysis of illicit heroin and opium samples on a coupled alumina and C18 column system is described. The compounds to be analysed can be divided into two groups: those with low pKa values, such as caffeine, papaverine and noscapine, and those with high pKa values, such as heroin, acetylcodeine, O6-monoacetylmorphine, procaine, codeine, morphine and strychnine. The first group can best be separated on a C18 column, whereas alumina is more suitable for the second group. Previously reported criteria for choosing proper buffer systems for ion-exchange separations on alumina were used together with an iterative regressive optimization procedure developed in our laboratory. The system can be used with and without valve-switching, depending on the sample type. The peak purity of the judicially important components heroin and O6-monoacetylmorphine has been checked with a photodiode array detector and by use of advanced software.

Chromatography, Liquid↗
PubMed1988

Separation of eight alkaloids and meconic acid and quantitation of five principal alkaloids in gum opium by gradient reversed-phase high-performance liquid chromatography.

The separation of the five principal alkaloids (morphine, codeine, thebaine, noscapine and papaverine), three minor alkaloids (laudanosine, cryptopine and narceine), meconic acid and some unidentified constituents in gum opium samples has been achieved on a reversed-phase phenyl column by gradient high-performance liquid chromatography using a simple and inexpensive mobile phase system. The linear gradient programme was started at 5% and ended at 70% methanol in triethylammonium phosphate buffer in 20 min. The five principal alkaloids were also determined with good precision. The method requires minimum sample preparation and is suitable for routine analysis.

Alkaloids↗
PubMed2003

Use of dynamically coated capillaries with added cyclodextrins for the analysis of opium using capillary electrophoresis.

A rapid, precise, accurate, and robust method using capillary electrophoresis (CE) with dynamically coated capillaries for the analysis of the major opium alkaloids in opium is presented. Dynamic coating of the capillary surface is accomplished using a commercially available reagent kit (polycation coating followed by polyanion coating). The addition of dual cyclodextrins (hydroxypropyl-beta-cyclodextrin and dimethyl-beta-cyclodextrin) to the run buffer imparts excellent selectivity for the opium alkaloids. For the determination of morphine, papaverine, codeine, noscapine and thebaine in opium gum and opium latex samples (using tetracaine as an internal standard) good agreement with values obtained by gradient high-performance liquid chromatography is obtained. Compared to the latter technique, CE affords better resolution with significantly faster analysis time (12 min versus 29 min). Dynamically coated capillaries, which give rise to a relatively high and robust electroosmotic flow (EOF) at the background electrolyte pH of 2.5, allow for rapid analysis and excellent migration time and peak area precision (RSDs < or = 0.12% and < or = 1.2%, respectively). Reproducible separations (relative migration times) for over 500 samples have been obtained on a single capillary. The nature of the injection solvent, the injection time and the contents of the waste vials have a profound effect on the pressure injection precision of the relatively hydrophobic solutes. The CE conditions reported in this study are also applicable to the analysis of lysergic acid diethylamide (LSD) exhibits.

Cyclodextrins↗
PubMed2003

Measuring the mitotic index in chemically-treated human lymphocyte cultures by flow cytometry.

In the human lymphocyte chromosome aberration assay, the mitotic index (MI) is the standard cytotoxic parameter for determining which test concentrations will be evaluated for chromosome aberrations. Assessment of the MI is performed microscopically by determining the frequency of mitotic cells in a population of 1000 cells. With the commercial availability of antibodies to the mitosis-specific marker, phosphorylated-histone H3 at serine 10, automating the assessment of the MI using flow cytometry is now possible [Cytometry 32 (1998) 71]. Our laboratory has utilized and validated this technology to measure the mitotic index of chemically-treated human lymphocyte cultures. Comparisons between the microscopic and flow MI frequencies from 24h treatments with mitomycin-C, aphidicolin, eugenol, etoposide, hydroxyrurea, potassium cyanide, staurosporine, ethyl alcohol, noscapine and colcemid((R)) are presented. Our results show that the mitosis specific H3-P marker is excellent for measuring the MI frequency in human lymphocyte cultures treated up to toxic concentrations. In addition, this study demonstrates that automation of analysis by flow cytometry is an excellent alternative to the microscopic method of analysis producing less variability than the microscopic scoring and a more complete dose response curve.

Adult↗
PubMed2006

Coated wire potentiometric detection for capillary electrophoresis studied using organic amines, drugs, and biogenic amines.

Capillary electrophoresis was coupled successfully and reliably to potentiometric sensors, which are based on an ionically conductive rubber phase coating, applied on a 250 microm diameter metal substrate. The membrane components included potassium tetrakis(p-chlorophenyl)borate (TCPB), bis(2-ethylhexyl)sebacate (DOS), and high molecular mass poly(vinyl chloride) (PVC). Potentiometry reveals a very sensitive CE detection mode, with sub-micromolar detection limits for amines and the randomly chosen drugs quinine, clozapine, cocaine, heroine, noscapine, papaverine, and ritodrine. The lowest detection limit, 1 x 10(-8) M injected concentration, was obtained for the quaternary ammonium compound tetrahexylammonium chloride. The more polar lower aliphatic amines and the biogenic amines dopamine, adrenaline, and cadaverine have much higher detection limits. The detection limits are log P dependent. Addition of a commercially available calixarene molecule or a synthetic macrocyclic amphiphilic receptor molecule to the electrode coatings enhanced the sensitivity respectively for the lower aliphatic amines and for the biogenic amines. A transpose of the Nikolskii-Eisenman-type function was suggested and used to convert the signal of the detector to a concentration-dependent signal.

Biogenic Amines↗
PubMed2005

Comparative qualitative and quantitative determination of alkaloids in narcotic and condiment Papaver somniferum cultivars.

In the present study morphinan, tetrahydrobenzylisoquinoline, benzo[c]phenanthridine, and phthalideisoquinoline alkaloids were determined qualitatively and quantitatively by HPLC and LC-MS analysis in tissues of the Tasmanian Papaver somniferum L. elite cultivar C048-6-14-64. The data were compared with the results from the low-morphine cultivar "Marianne". In the elite cultivar, 91.2% of the latex alkaloids consist of the three pharmaceutically most valuable alkaloids: morphine, codeine, and thebaine. In the root system, the major alkaloids are sanguinarine/10-hydroxysanguinarine and dihydrosanguinarine/10-hydroxydihydrosanguinarine. In the stems and leaves of C048-6-14-64, the same alkaloids were measured as in the latex. In the stems, a gradient in relative total alkaloid content from the top downward toward the roots was observed. The concentration of morphine was decreasing toward the roots, whereas an increasing gradient from the upper to the lower stem parts was detected for codeine. The relative total alkaloid concentration in leaves remained constant; no gradient was observed. The cultivar "Marianne" displayed a shifted pattern of alkaloid accumulation and reduced levels of total alkaloid. In the condiment cultivar, 80.5% of the alkaloids of the latex consisted of the two phthalideisoquinoline alkaloids narcotoline and noscapine. Only 18.8% of the relative total alkaloid content were morphinan alkaloids. In contrast to the narcotic cultivar, in which the benzo[c]phenanthridines in roots dominated over the morphinan and tetrahydrobenzylisoquinoline alkaloids, the concentration of benzo[c]phenanthridines in "Marianne" was similar to that of morphinan and tetrahydrobenzylisoquinoline alkaloids. These data suggest a differential alkaloid regulation in each cultivar of P. somniferum.

Alkaloids↗
PubMed1981

The separation and quantitation of the narcotic components of illicit heroin using reversed-phase high performance liquid chromatography.

The separation of heroin from other narcotic components of illicit preparations is achieved by high performance liquid chromatography. Using an aminopropyl bonded silica packing and a mixture of 85% acetonitrile and 15% 0.005 M tetrabutylammonium phosphate as the mobile phase, caffeine, heroin, acetylcodeine, 6-acetylmorphine, codeine, and morphine are separated from each other and are accurately quantified. Papaverine, noscapine, thebaine, and strychnine are also separated from these principal components.

Caffeine↗
PubMed2001

Detection of non-prescription heroin markers in urine with liquid chromatography-atmospheric pressure chemical ionization mass spectrometry.

The planned introduction of a prescription heroin program in Germany created a need for differentiation between non-prescription and prescribed diamorphine use. The following substances were chosen as markers of non-prescription heroin: acetylcodeine (AC); its metabolites codeine (C) and codeine 6-glucuronide (C6G); papaverine (P); and noscapine (N). Typical heroin markers diamorphine (DAM) and its metabolites monoacetylmorphine (MAM) and morphine (M) were also determined. The drugs were extracted from urine samples with solid-phase extraction (C18) using standard 200-mg columns and 96-well microplates (100 mg). The extracts were examined with liquid chromatography-atmospheric pressure chemical ionization mass spectrometry (positive ionization) in two isocratic systems. Selected ion monitoring procedures were applied for protonated molecular masses and characteristic fragments of drugs involved. The limits of detection were in the range of 0.5-1 ng/mL urine. The occurrence of selected heroin markers was investigated in 25 urine samples collected from heroin abusers (road traffic offenders and overdosed patients). C6G was found in all samples, C in 24 samples, N in 22 samples, MAM in 16 samples, P in 14 samples, DAM in 12 samples, and AC in 4 samples. The appearance of these compounds in urine reflects their pharmacokinetic properties and the composition of non-prescription heroin.

Adult↗
PubMed2005

Drug-resistant T-lymphoid tumors undergo apoptosis selectively in response to an antimicrotubule agent, EM011.

We have shown previously that EM011, a synthetic compound, binds tubulin with a higher affinity than the founding compound, noscapine, without changing total microtubule polymer mass. Now we show that EM011 is potently effective against vinblastine-resistant human lymphoblastoid line CEM/VLB100 and its parental vinblastine-sensitive line CEM. The cytotoxicity is mediated by cell cycle arrest at G2/M phase and subsequent apoptosis, as indicated by altered plasma membrane asymmetry, loss of mitochondrial transmembrane potential, activation of caspase-3, and increased DNA fragmentation. Furthermore, oral EM011 treatment of nude mice bearing human lymphoma xenografts results in pronounced tumor regression by triggering apoptosis and significantly lengthens the survival time of mice. EM011 treatment does not have obvious side effects in tissues with frequently dividing cells, such as the spleen and duodenum. In addition, EM011 does not show any toxicity in the liver, lung, heart, brain, and sciatic nerve. More importantly, EM011 does not affect hematopoiesis as determined by complete blood count profiles. These findings suggest that EM011 may be a safe and effective chemotherapeutic agent for oral treatment of drug-resistant human lymphomas.

Animals↗
PubMed2005

A rapid and reliable solid-phase extraction method for high-performance liquid chromatographic analysis of opium alkaloids from papaver plants.

A rapid and reliable solid-phase extraction method for HPLC analysis of opium alkaloids from Papaver plants was established. Fifty mg of dried and powdered plant sample was extracted with 5 ml of 5% acetic acid for 30 min under sonication. After centrifugation, 3 ml of the supernatant was loaded on a reversed-phase cation-exchange solid-phase extraction cartridge. After seriate washings with 0.1 M hydrochloric acid and methanol, alkaloids were eluted with a mixture of 28% ammonia and methanol (1:19). The eluate was concentrated under nitrogen stream at 40 degrees C and the residue was dissolved in 50% aqueous methanol for high performance liquid chromatographic analysis. With this solid-phase extraction method, the recovery of morphine, codeine, oripavine, thebaine, papaverine, noscapine and sanguinarine was from 99.94 to 112.18% when the standard alkaloids were added to the plant samples. Opium alkaloids of a variety of genus Papaver plants cultivated in a field and phytotron were analyzed by this method.

Alkaloids↗
PubMed1998

[Mechanisms of central antitussives].

This paper provides an overview of our current understanding of the central mechanisms of cough and antitussives. Systemic administration of 8-OH-DPAT at doses of 0.1 and 0.3 mg/kg, i.p. markedly reduced the number of coughs in rats in a dose-dependent manner. The antitussive effect of 8-OH-DPAT, dihydrocodeine and dextromethorphan significantly was reduced by pretreatment with methysergide, but not ketanserin. Therefore, it is possible to speculate that the 5-HT1 receptors, in particular the 5-HT1A receptors, may be more important than others with respect to the effect of antitussive drugs. DAMGO, a selective mu-opioid receptor agonist, and U-50,488H, a highly selective kappa-opioid receptor agonist, have potent antitussive effects when administered either i.c. or i.p. However, we did not observe a cough-depressant effect of DPDPE, a selective delta-opioid receptor agonist. These results indicate that the antitussive effects of opioids are mediated predominantly by mu- and kappa-opioid receptors. On the other hand, naloxonazine, a selective mu 1-opioid receptor antagonist, had no effect on the antitussive effects associated with i.c.v. DAMGO. These results indicate that mu 2-rather than mu 1-opioid receptors are involved in mu-opioid receptor-induced antitussive effects. Antitussive effects of dextromethorphan and noscapine were significantly and dose-dependently reduced by pretreatment with rimcazole, a specific antagonist of sigma sites. However, rimcazole did not have a significant effect on the antitussive effect of morphine. These results suggest that sigma sites may be involved in the antitussive mechanism of non-narcotic antitussive drugs.

8-Hydroxy-2-(di-n-propylamino)tetralin↗
PubMed1999

[Possible role of sigma-receptors in the regulation of cough reflex, gastrointestinal and retinal function].

This paper provides an overview of our current understanding of the role of sigma-receptors in the regulation of cough, gastrointestinal and retinal function. Systemic administration of N-(+)-allylnormetazocine ((+)SKF-10,047), 1,2-di-(2-toyl)guanidine (DTG) or pentazocine markedly reduced the number of coughs in a dose-dependent manner. The antitussive effect of these sigma-receptor ligands was significantly reduced by pretreatment with haloperidol or rimcazol, a specific antagonist of sigma-receptors. Antitussive effects of dextromethorphan and noscapine were significantly and dose-dependently reduced by pretreatment with rimcazole. However, rimcazole did not have a significant effect on the antitussive effect of morphine. These results suggest that haloperidol-sensitive sigma-receptors may be involved in the antitussive mechanism of non-narcotic antitussive drugs. Selective sigma-receptor ligands such as (+)SKF-10,047, DTG and (+)pentazocine elicit a potent protection against gastric and duodenal ulcers. Ulcerprotective activity of sigma-receptor ligands may be related to their stimulating effect on bicarbonate secretion through interaction with sigma-receptors in the gastrointestinal mucosa. Activation of sigma-receptors in retina protect retinal cells against glutamate-induced neurotoxicity. It is possible that sigma-receptor ligands may be useful as therapeutic drugs against retinal disease with ischemia-induced neuronal cell death such as retinal artery occlusion, diabetes mellitus or glaucoma.

Animals↗
PubMed2006

Interaction of papaverine with the enalapril-induced cough in guinea pig.

BACKGROUND: Angiotensin Converting Enzyme Inhibitors (ACEIs) like enalapril are extremely effective in the treatment of hypertension and heart failure. One of the most important side-effects of these drugs which can lead to cessation of therapy is a persistant dry cough, induced because of increased bradykinin levels in the lung. Although antitussive alkaloids like codeine are effective in suppressing this cough, they too present a wide range of side-effects, most notably addiction. OBJECTIVE: In a previous work we were able to show that noscapine, a non-narcotic antitussive agent, was able to decrease enalapril induced cough in guinea pigs. In this work, papaverine, another non-narcotic alkaloid found in opium latex was tested in the guinea pig model for antitussive activity. METHOD: Cough was induced in enalapril pretreated guinea pigs by forcing the animals to inspire capsaicin aerosol in an air-tight chamber. Coughs were recorded in control animals and in those which had received different doses of papaverine. Characteristic changes in chamber air pressure, were detected by a pressure transducer. RESULTS: . At low doses (0.5 and 0.25 mg/kg) papaverine was able to decrease enalapril induced cough. CONCLUSION. This effect was not mediated by the action of the drug on mu receptors and was only observed in animals treated with enalapril.

Angiotensin-Converting Enzyme Inhibitors↗
PubMed2001

Isoquinoline alkaloid production by transformed cultures of Papaver somniferum.

Three clones of transformed cultures of opium poppy (Papaver somniferum L.) were established by infection with Agrobacterium rhizogenes MAFF 03-01724. MAFF clone 1 being capable of forming somatic embryos was selected and its growth and isoquinoline alkaloid production was investigated. The illumination, temperature and nutrient medium composition greatly affected growth, cell morphology and alkaloid accumulation. The MAFF clone 1 cultured in Root Culture medium in the dark at 22 degrees C accumulated a high quantity of sanguinarine (652 micrograms/g dry weight) though the growth was poor (4.4 fold as fresh weight basis after 2 months of culture). The MAFF clone 1 cultured in a quarter macro salt strength Woody Plant medium under 14 h/day light at 22 degrees C developed into plantlets and accumulated significant quantity of codeine (648 micrograms/g dry wt) together with papaverine, noscapine, and sanguinarine. This clone was applied to a rotating drum fermenter (2 L working volume), and ca. 0.3 mg codeine and 0.06 mg sanguinarine were obtained after 4 weeks of culture. One quarter of the codeine produced was found in the culture medium.

Alkaloids↗
PubMed2002

GC/MS determination of pyrolysis products from diacetylmorphine and adulterants of street heroin samples.

The inhalation of heroin vapors after heating on aluminium foil ("chasing the dragon") is gaining popularity nowadays among heroin users seeking to avoid the risks of parenteral drug administration. The heroin-smoking procedure was simulated under laboratory conditions by heating the samples on aluminium foil at 250 to 400 degrees C and collecting the vapors in a condenser trap. A total of 72 pyrolysis products of diacetylmorphine, street heroin, residues from aluminium foils used to smoke street heroin, typical by-products, and adulterants were detected by gas chromatography/mass spectrometry (GC/MS). About half of these compounds could be identified. Diacetylmorphine (base and salt) undergoes substantial to complete degradation. Some typical street heroin constituents, like morphine, codeine, acetylcodeine, papaverine, and caffeine, are rather heat-stable. Other compounds, like noscapine and paracetamol, are pyrolyzed to a greater extent. The principal chemical reactions leading to the formation of pyrolysis products are desacetylation, transacetylation, N-demethylation, O-methylation, ring cleavage and oxydation.

Drug Contamination↗
PubMed1990

[Efficacy and side effects of epidural opioids depending on the site of surgery].

We reported the requirement of supplemental analgesics following epidural opioids including Opial 5mg and 10mg, and morphine HCl 2.5mg, for 24 hours in postoperative period after surgery of body surface, and lower and upper abdominal surgeries. Incidence of their side effects was also observed. Opial contains 50% morphine HCl and other opioids such as codeine, thebaine, papaverine, and noscapine etc. After upper abdominal surgeries, patients required additional analgesics more frequently. Kinds and doses of opioids used, suggest that epidural administration of other opioids contained in Opial has some analgesic effect. After the surgery of body surface the opioid requirement may be influenced by the intraoperative anesthetic technics and the state of mind of the patient. Urinary retention was the most interesting side effect observed and our data suggest that papaverine contained in Opial may have favorable effect and morphine HCl may have adverse effects regarding its incidence.

Analgesia, Epidural↗
PubMed1988

[Pharmacotherapy of cough].

The optimal approach to the treatment of cough consists, first, in determination of its precise cause. Treatment should be directed at the specific etiology or the pathophysiologic mechanism responsible for cough. The outcome of specific treatment is almost always successful. However, there are also situations in which the cause of cough is unknown or in which the cough does not serve any useful purpose but prevents rest and sleep. In such cases symptomatic treatment with antitussives may be indicated. Centrally acting antitussives such as opium alkaloids, dextromethorphan and noscapine are the most effective drugs. The indication for expectorants lacks scientifically based support.

Anesthetics, Local↗
PubMedDate not supplied

An evaluation of TLC systems for opiate analysis.

The authors selected 38 thin-layer-chromatography (TLC) systems described in the available literature published over the last 10 years and evaluated those systems with respect to their suitability for detection and identification of opiates in urine, opium and heroin, as well as adulterants in heroin. A total of 14 substances: 8 opiates (morphine, 6-monoacetylmorphine, diacetylmorphine, codeine, acetylcodeine, noscapine, papaverine and thebaine) and 6 adulterants (ephedrine, quinine, methadone, caffeine, cocaine and strychnine) were used as test samples for this research. Using laboratory-coated plates and pre-coated plates, 15 and 13 TLC systems, respectively, were found to be able to detect and identify morphine and codeine in urine without interference from the remaining 12 substances. For the detection of opiates in opium samples as well as opiates and adulterants in illicit heroin samples the TLC system: chloroform-n-hexane-triethylamine (9:9:4) which was developed by the National Drug Research Centre, Penang, Malaysia, was found to be most suitable on both laboratory-coated and pre-coated plates. In addition, the following two systems, one on laboratory-coated plates--hexane-chloroform-diethylamine (50:30:7)--and the other on pre-coated plates--benzene-dioxane-ethanol-ammonia (50:40:5:5; T-7)--were also found to be among most suitable TLC systems for the analysis of opiates in opium samples. The article also presents the relative cost of each of the 38 evaluated TLC systems.

Chromatography, Thin Layer↗