Thebaine

from Wikipedia, the free encyclopedia
Structural formula
Structure of thebaine
General
Surname Thebaine
other names
  • Paramorphine
  • (5 R , 9 R , 13 S ) -3,6-dimethoxy- N -methyl-4,5-epoxymorphine-6,8-diene ( IUPAC )
Molecular formula C 19 H 21 NO 3
Brief description

colorless leaflets

External identifiers / databases
CAS number 115-37-7
EC number 204-084-1
ECHA InfoCard 100.003.713
PubChem 5321926
ChemSpider 4479543
Wikidata Q410169
properties
Molar mass 311.37 g · mol -1
Physical state

firmly

density

1.31 g cm −3

Melting point

190-193 ° C , sublimed at 170-180 ° C

pK s value

6.05

solubility
safety instructions
GHS labeling of hazardous substances
06 - Toxic or very toxic

danger

H and P phrases H: 301-310-330
P: 260-280-284-301 + 310-302 + 350-310
Toxicological data

54 mg kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Thebaine ( paramorphine ) is an organic-chemical natural substance and belongs to the group of opiates .

Occurrence

Poppy seeds, Papaver bracteatum , whose milky sap contains thebaine.

Thebaine is particularly found in the milk juice of medicinal poppy seeds ( Papaver bracteatum ) in proportions of up to 26%. The content in the opium is up to 0.2-0.5%. Thebaine is used as a raw material for the manufacture of certain opioids and opioid antagonists. It has no therapeutic application itself.

In the case of the opium poppy , the milky sap is formed in the capsule as well as in the stem and the leaves. However, it is not contained in the ripe seeds. However, varieties such as the opium poppy, which are also used as food, can come into contact with the milky sap during mechanical harvesting and thus become contaminated with thebaine. In this way, thebaine can be accidentally ingested with food.

In 2018, the Federal Institute for Risk Assessment pointed out insufficient toxicological knowledge and incomplete information on the amount of poppy seeds consumed in Germany. The institute advised that care should be taken in food production to reduce the levels of opium alkaloids, including thebaine, as far as technically possible.

history

Thebain was discovered by Pierre Joseph Pelletier in 1833 , the structure was determined by Clemens Schöpf . The name is derived from the ancient Egyptian name of today's city of Luxor , Thebes , which was built in the 18th and 19th centuries. It was a center of the opium trade in the 18th century and where the opium Thebaicum , a powdery mass made from opium, was obtained as early as the Middle Ages .

effect

Thebaine has a stronger stimulating effect, but has a weaker analgesic effect than morphine , inhibits cholinesterase and, in high concentrations, causes strychnine- like cramps (convulsive poison ).

Thebain falls under the Narcotics Act .

use

Buprenorphine is produced from thebaine using the Diels-Alder reaction . Also, oxycodone , naloxone , nalbuphine , oxymorphone and etorphine can be synthesized from thebaine.

Individual evidence

  1. ↑ a b c d e f Entry on Thebain. In: Römpp Online . Georg Thieme Verlag, accessed on December 28, 2014.
  2. ↑ a b c d Thebaine data sheet at Sigma-Aldrich , accessed on April 24, 2011 ( PDF ).
  3. ↑ a b Entry on thebaine in the ChemIDplus database of the United States National Library of Medicine (NLM) .
  4. ↑ Hermann Ammon (Ed.): Hunnius Pharmaceutical Dictionary . 8th edition, de Gruyter, Berlin 2004, ISBN 3-11-015792-6 .
  5. ↑ Federal Institute for Risk Assessment: Poppyseed in Food: The content of the opium alkaloid thebaine should be reduced as much as possible. December 7, 2018, accessed July 11, 2019 .
  6. ↑ Gundolf Keil : "blutken - bloedekijn". Notes on the etiology of the hyposphagma genesis in the 'Pommersfeld Silesian Eye Booklet' (1st third of the 15th century). With an overview of the ophthalmological texts of the German Middle Ages. In: Specialized prose research - Crossing borders. Volume 8/9, 2012/2013, pp. 7–175, here: p. 54.