Northebaine was identified as the major metabolite formed during the biotransformation of thebaine by Mucor piriformis. Minor metabolites identified are isomeric thebaine N-oxides. Among isomeric thebaine Noxides, the one with the equatorial oxygen attached to the nitrogen is relatively unstable. Resting cells. grown in the presence of thebaine for 24 hr, efficiently converted thebaine into nor...

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 o...

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 sample...

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) ...

Metal to ligand complex with molecular formula [Co (L)]Cl2 , (L= thebaine) of thebaine as an alkaloid and its cobalt complex have been prepared and characterized by elemental analysis, 1H-NMR, IR and UV-Visible spectroscopy. The Biological activity of alkaloids is believed to increase when they are coordinated with transition metal ions. However, the literature on this subject is contradictory ...

The photooxidation of thebaine (3) with a sun lamp affords two main products: hydrodibenzofuran 10 (major) and benzofuran 11 (minor). The latter compound becomes predominant if a Hg lamp is used instead of a sun lamp. The formation of 10 proceeds via an endoperoxide intermediate that undergoes oxidation at the nitrogen atom. Protection of the nitrogen either by protonation or quaternization pre...

As part of a research programme to establish an analytical method for the simultaneous detection of the five major opium alkaloids in poppy seeds by liquid chromatography-electrospray ionization-mass spectrometry (LC-ESI-MS) it was discovered that the inclusion of thebaine produced two peaks for the same compound. This was in contrast to the effective simultaneous detection, by LC-ESI-MS, of mo...

background & aim: papaver bracteatum lindl.  (papaverace) is an important pharmaceutical plant which contains isoqinoline alkaloids. isoqinoline alkaloids constitute one distinct group of secondary metabolites of the papaverace family. codeine and thebaine are important alkaloids of papaver bracteatum which use widely due to its medicinal properties. therefore it is necessary to determinati...

The rearrangement reaction of thebaine (1) with methanesulfonic acid, in the presence of hydrogen sulfide, resulted in a sulfide-type bisaporphine 13, instead of the expected thiol 12. The acidic hydrolysis of the thiocyanato derivatives 3, 9, 20 and 21, obtained from thebaine (1), as well as the reduction of 9 and 21 with sodium borohydride yielded disulfide-type bisaporphines 16 and 23.

Opiates such as morphine and codeine are mainly obtained by extraction from opium poppies. Fermentative opiate production in microbes has also been investigated, and complete biosynthesis of opiates from a simple carbon source has recently been accomplished in yeast. Here we demonstrate that Escherichia coli serves as an efficient, robust and flexible platform for total opiate synthesis. Thebai...