Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/08/06 17:05:17」(JST)

wiki en

Thebaine (paramorphine), is an opiate alkaloid, its name coming from the Greek Θῆβαι, Thēbai, an ancient city in Upper Egypt. A minor constituent of opium, thebaine is chemically similar to both morphine and codeine, but has stimulatory rather than depressant effects. At high doses, it causes convulsions similar to strychnine poisoning. The "unnatural" enantiomer (+)-thebaine does show analgesic effects apparently mediated through opioid receptors, unlike the inactive natural enantiomer (-)-thebaine.^[3] Thebaine is not used therapeutically, but as the main alkaloid extracted from Papaver bracteatum (Iranian Poppy), it can be converted industrially into a variety of compounds including oxycodone, oxymorphone, nalbuphine, naloxone, naltrexone, buprenorphine and etorphine.

Thebaine is controlled under international law, is listed as a Class A drug under the Misuse of Drugs Act 1971 in the United Kingdom, and is controlled as a Schedule II of the Controlled Substances Act in the United States of America.

This alkaloid is biosynthetically related to salutaridine, oripavine, morphine and reticuline.^[4]

References[edit source | edit]

^ Mikus G, Somogyi AA, Bochner F, Eichelbaum M. "Thebaine O-demethylation to oripavine: genetic differences between two rat strains." Xenobiotica. 1991 Nov; 21(11):1501-9. PMID 1763524
^ WHO Advisory Group. "The dependence potential of thebaine." Bulletin on Narcotics. 1980; 32(1):45–54. Accessed October 5, 2007. PMID 6778542
^ Aceto MD, Harris LS, Abood ME, Rice KC. "Stereoselective mu- and delta-opioid receptor-related antinociception and binding with (+)-thebaine." European Journal of Pharmacology. 1999 Jan 22;365(2-3):143-7. PMID 9988096
^ Novak et al. "Morphine Synthesis and Biosynthesis—An Update" Current Organic Chemistry (2000) 4, 343-362. http://brocku.ca/mathematics-science/departments-and-centres/chemistry/faculty/Hudlicky/CurrOrgChem-2000-4-343.pdf

English Journal

Design and implementation of an automated liquid-phase microextraction-chip system coupled on-line with high performance liquid chromatography.

Li B1, Petersen NJ2, Payán MD3, Hansen SH1, Pedersen-Bjergaard S4.Author information 1Department of Pharmacy, Faculty of Health and Medical Sciences, University of Copenhagen, Universitetsparken 2, 2100 Copenhagen, Denmark.2Department of Pharmacy, Faculty of Health and Medical Sciences, University of Copenhagen, Universitetsparken 2, 2100 Copenhagen, Denmark. Electronic address: nickolaj.petersen@sund.ku.dk.3Department of Analytical Chemistry, Faculty of Chemistry, University of Seville, P.O. Box 41012, Seville, Spain.4Department of Pharmacy, Faculty of Health and Medical Sciences, University of Copenhagen, Universitetsparken 2, 2100 Copenhagen, Denmark; School of Pharmacy, University of Oslo, P.O Box 1068 Blindern, 0316 Oslo, Norway.AbstractAn automated liquid-phase microextraction (LPME) device in a chip format has been developed and coupled directly to high performance liquid chromatography (HPLC). A 10-port 2-position switching valve was used to hyphenate the LPME-chip with the HPLC autosampler, and to collect the extracted analytes, which then were delivered to the HPLC column. The LPME-chip-HPLC system was completely automated and controlled by the software of the HPLC instrument. The performance of this system was demonstrated with five alkaloids i.e. morphine, codeine, thebaine, papaverine, and noscapine as model analytes. The composition of the supported liquid membrane (SLM) and carrier was optimized in order to achieve reasonable extraction performance of all the five alkaloids. With 1-octanol as SLM solvent and with 25mM sodium octanoate as anionic carrier, extraction recoveries for the different opium alkaloids ranged between 17% and 45%. The extraction provided high selectivity, and no interfering peaks in the chromatograms were observed when applied to human urine samples spiked with alkaloids. The detection limits using UV-detection were in the range of 1-21ng/mL for the five opium alkaloids presented in water samples. The repeatability was within 5.0-10.8% (RSD). The membrane liquid in the LPME-chip was regenerated automatically between every third injection. With this procedure the liquid membrane in the LPME-chip was stable in 3-7 days depending on the complexity of sample solutions with continuous operation. With this LPME-chip-HPLC system, series of samples were automatically injected, extracted, separated, and detected without any operator interaction.
Talanta.Talanta.2014 Mar;120:224-9. doi: 10.1016/j.talanta.2013.12.016. Epub 2013 Dec 14.
An automated liquid-phase microextraction (LPME) device in a chip format has been developed and coupled directly to high performance liquid chromatography (HPLC). A 10-port 2-position switching valve was used to hyphenate the LPME-chip with the HPLC autosampler, and to collect the extracted analytes
PMID 24468363

Enhanced thebaine production in Papaver bracteatum cell suspension culture by combination of elicitation and precursor feeding.

Zare N1, Farjaminezhad R, Asghari-Zakaria R, Farjaminezhad M.Author information 1a Department of Agronomy and Plant Breeding , Faculty of Agriculture, University of Mohaghegh Ardabili , Ardabil , Iran.AbstractIn this study, the effect of methyl jasmonate (MJ) and ultrasound (US), individually and in combination with L-tyrosine, on the stimulation of thebaine production in Papaver bracteatum cell suspension cultures was studied. The addition of L-tyrosine did not significantly affect the cell biomass, but significantly increased the thebaine yield of cells compared with the control. The synergistic effects of MJ and L-tyrosine in the combined treatment of 100 μM MJ and 2 mM L-tyrosine increased the thebaine yield of cells up to 84.62 mg L- 1 at 6 days after treatment. Sonication of the cells for 20 s caused a significant decrease in cell growth and biomass, whereas the thebaine yield increased up to 39.60 mg L- 1 at 6 days after treatment. The combination of US (10 s) and L-tyrosine feeding (2 mM) significantly increased the production of thebaine in comparison to individual utilisation of 2 mM L-tyrosine and US (10 s).
Natural product research.Nat Prod Res.2014 Feb 5. [Epub ahead of print]
In this study, the effect of methyl jasmonate (MJ) and ultrasound (US), individually and in combination with L-tyrosine, on the stimulation of thebaine production in Papaver bracteatum cell suspension cultures was studied. The addition of L-tyrosine did not significantly affect the cell biomass, but
PMID 24499458

Microbe associated molecular patterns from rhizosphere bacteria trigger germination and Papaver somniferum metabolism under greenhouse conditions.

Bonilla A1, Sarria AL2, Algar E1, Muñoz Ledesma FJ3, Ramos Solano B4, Fernandes JB5, Gutierrez Mañero FJ1.Author information 1Faculty of Pharmacy, San Pablo CEU University, PO Box 67, Boadilla del Monte, 28668 Madrid, Spain.2Universidade Federal de São Carlos, Laboratório de Produtos Naturais, Departamento de Química, São Carlos, SP 13.565-905, Brazil; Faculty of Pharmacy, San Pablo CEU University, PO Box 67, Boadilla del Monte, 28668 Madrid, Spain.3ALCALIBER I+D+i, S.L.U. Ctra, Carmona-El Viso del Alcor, km. 18, 41410 Carmona, Sevilla, Spain.4Faculty of Pharmacy, San Pablo CEU University, PO Box 67, Boadilla del Monte, 28668 Madrid, Spain. Electronic address: bramsol@ceu.es.5Universidade Federal de São Carlos, Laboratório de Produtos Naturais, Departamento de Química, São Carlos, SP 13.565-905, Brazil.AbstractTen PGPR from different backgrounds were assayed on Papaver somniferum var. Madrigal to evaluate their potential as biotic elicitors to increase alkaloid content under the rationale that some microbe associated molecular patterns (MAMPs) are able to trigger plant metabolism. First, the 10 strains and their culture media at two different concentrations were tested for their ability to trigger seed germination. Then, the best three strains were tested for their ability to increase seedling growth and alkaloid levels under greenhouse conditions. Only three strains and their culture media enhanced germination. Then, germination enhancing capacity of these best three strains, N5.18 Stenotrophomonas maltophilia, Aur9 Chryseobacterium balustinum and N21.4 Pseudomonas fluorescens was evaluated in soil. Finally, the three strains were applied on seedlings at two time points, by soil drench or by foliar spray. Photosynthesis was measured, plant height was recorded, capsules were weighted and alkaloids analyzed by HPLC. Only N5.18 delivered by foliar spray significantly increased plant height coupled to an increase in total alkaloids and a significant increase in opium poppy straw dry weight; these increases were supported by a better photosynthetic efficiency. The relative contents of morphine, thebaine, codeine and oripavine were affected by this treatment causing a significant increase in morphine coupled to a decrease in thebaine, demonstrating the effectivity of MAMPs from N5.18 in this plant species. Considering the increase in capsule biomass and alkaloids together with the acceleration of germination, strain N5.18 appears as a good candidate to elicit plant metabolism and consequently, to increase productivity of Papaver somniferum.
Plant physiology and biochemistry : PPB / Société française de physiologie végétale.Plant Physiol Biochem.2014 Jan;74:133-40. doi: 10.1016/j.plaphy.2013.11.012. Epub 2013 Nov 19.
Ten PGPR from different backgrounds were assayed on Papaver somniferum var. Madrigal to evaluate their potential as biotic elicitors to increase alkaloid content under the rationale that some microbe associated molecular patterns (MAMPs) are able to trigger plant metabolism. First, the 10 strains an
PMID 24296249

Japanese Journal

A Rapid and Reliable Solid-Phase Extraction Method for High-Performance Liquid Chromatographic Analysis of Opium Alkaloids from Papaver Plants

YOSHIMATSU Kayo,KIUCHI Fumiyuki,SHIMOMURA Koichiro,MAKINO Yukiko
Chemical & pharmaceutical bulletin 53(11), 1446-1450, 2005-11-01
… 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. …
NAID 10016784457

Simultaneous analysis of Thebaine, 6-MAM and six abused opiates in postmortem fluids and tissues using Zymark^【○!R】 automated solid-phase extraction and gas chromatography-mass spectrometry

LEWIS R. J.,JOHNSON R. D.,HATTRUP R. A.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 822(1), 137-145, 2005-08-05
NAID 10016978932

「麻薬」

Thebaine
	IUPAC name 6,7,8,14-tetradehydro-4,5a-epoxy-; 3,6-dimethoxy-17-methylmorphinan
	Other names Paramorphine
Identifiers
CAS number	115-37-7
PubChem	5324289
ChemSpider	4481822 , 4479543
UNII	2P9MKG8GX7
KEGG	C06173
MeSH	Thebaine
ChEBI	CHEBI:9519
ChEMBL	CHEMBL403893
Jmol-3D images	Image 1
	SMILES O(c5ccc4c2c5O[C@H]3C(/OC)=C\C=C1\[C@H](N(CC[C@]123)C)C4)C ;
	InChI InChI=1S/C19H21NO3/c1-20-9-8-19-12-5-7-15(22-3)18(19)23-17-14(21-2)6-4-11(16(17)19)10-13(12)20/h4-7,13,18H,8-10H2,1-3H3/t13-,18+,19+/m1/s1 ; Key: FQXXSQDCDRQNQE-VMDGZTHMSA-N ;
Properties
Molecular formula	C19H21NO3
Molar mass	311.37 g mol−1
Pharmacology
Metabolism	O-demethylation
Legal status	Class A(UK) Schedule II(US)
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references

　　[★]

英: narcotic narcotics, narcotic drugs
ラ: narcotica
関

日本の法医学上の定義

麻薬取締法によって規制を受けていた薬物。現在、法律上は麻薬及び向精神薬取締法となっている。

分類

SLE.62

麻薬性鎮痛薬 narcotic analgesics

1. アヘンアルカロイド系 opium alkaloids (いわゆるオピオイド)

a. アヘン及び精製アルカロイド

アヘン opium：複数のアルカロイドが含まれている

b. モルヒネ誘導体

2. 合成麻薬

中枢神経興奮薬 stimulants

3. コカアルカロイド系 coca alkaloids

ニュース

レディー・ガガの麻薬使用発言に批判集中！音楽制作では「麻薬が刺激になった」

2010年8月29日 1時22分
シネマトゥデイ映画ニュース
奇抜な衣装と大胆なパフォーマンスが人気のスター、レディー・ガガが、自身の創造性について「麻薬が刺激を与えてくれた」と発言した。

「テバイン」

　　[★]

英: thebaine
関: ケシ

ケシアルカロイド

[mikus1991-1] Mikus G, Somogyi AA, Bochner F, Eichelbaum M. "Thebaine O-demethylation to oripavine: genetic differences between two rat strains." Xenobiotica. 1991 Nov; 21(11):1501-9. PMID 1763524

[who1980-2] WHO Advisory Group. "The dependence potential of thebaine." Bulletin on Narcotics. 1980; 32(1):45–54. Accessed October 5, 2007. PMID 6778542

[aceto_1999-3] Aceto MD, Harris LS, Abood ME, Rice KC. "Stereoselective mu- and delta-opioid receptor-related antinociception and binding with (+)-thebaine." European Journal of Pharmacology. 1999 Jan 22;365(2-3):143-7. PMID 9988096

[4] Novak et al. "Morphine Synthesis and Biosynthesis—An Update" Current Organic Chemistry (2000) 4, 343-362. http://brocku.ca/mathematics-science/departments-and-centres/chemistry/faculty/Hudlicky/CurrOrgChem-2000-4-343.pdf

匿名

検索

案内

案内

thebaine