Chelerythrine

Structural formula
General
Surname	Chelerythrine
other names	1,2-Dimethoxy-12-methyl [1,3] benzodioxolo [5,6-c] phenanthridinium
Molecular formula	C 21 H 18 NO 4 +
Brief description	colorless solid
External identifiers / databases
CAS number 34316-15-9 3895-92-9 (chloride) EC number 251-930-0 ECHA InfoCard 100.047.194 PubChem 2703 ChemSpider 2602 Wikidata Q5089853
properties
Molar mass	348.37 g mol −1
Physical state	firmly
Melting point	213 ° C (chloride)
solubility	practically insoluble in water Easily soluble in absolute alcohol
safety instructions
GHS hazard labeling no classification available
Toxicological data	95 mg kg −1 ( LD 50 ,  mouse ,  sc )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Chelerythrine is a chemical compound from the group of quaternary benzophenanthridines .

Occurrence

Chelerythrine occurs naturally in celandine ( Chelidonium majus ). It is the most effective alkaloid (content up to 2%) in the plant. It is also found in other plants such as California poppy ( Eschscholtzia californica ) and various types of horned poppy .

history

In 1839, JMA Probst made the alkaloid chelerythrine from the celandine and the yellow horn poppy . In 1842 Jacob Heinrich Wilhelm Schiel (1813–1889) stated that the American chemist James Freeman Dana (1793–1827) made it from the Canadian roots in 1828 Bloodweed ( Sanguinaria canadensis ) represented sanguinarine is identical to Probst's chelerythrine. In 1869 Ludwig Weyland tried sanguinarine (chelerythrine) in animal experiments on the frog. According to Husemann (1871 and 1883), 0.06 g of the alkaloid known as chelerythrine and sanguinarine caused vomiting in humans, and 0.001 g subcutaneously killed frogs and 0.02 g rabbits. Symptoms of poisoning resulted in adynamia and clonic or even tonic convulsions . Death resulted from paralysis of the respiratory center . Small doses increased the pulse rate and blood pressure, while large doses reduced it by paralyzing the vasomotor center and the heart.

properties

Chelerythrine is a colorless solid, its salts being yellow in color and fluorescing in aqueous solution. Chelerythrine combines with acids to form salts that are soluble in water.

use

Chelerythrine is recommended as an antimicrobial and anti-inflammatory agent against infections of the oral cavity and is an inhibitor of rat liver aminotransferase , a potent cytotoxic agent and decoupler of oxidative phosphorylation .

safety instructions

Chelerythrine is locally irritating and when taken orally causes vomiting, gastroenteritis and severe diarrhea . In larger doses it has central paralyzing effects and causes death from respiratory paralysis.

Individual evidence

1. ↑ ^{a b} W.LF Armarego: Purification of Laboratory Chemicals . Butterworth-Heinemann, 2017, ISBN 978-0-12-805456-7 , pp. 463 ( limited preview in Google Book search).
2. ↑ ^{a b c} Entry on Benzo [c] phenanthridine alkaloids. In: Römpp Online . Georg Thieme Verlag, accessed on July 2, 2019.
3. ↑ ^{a b c} Zeno.org: Chelerythrine , accessed July 2, 2019.
4. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
5. ↑ ^{a b c} Franz-Xaver Reichl: Pocket Atlas of Toxicology Substances, Effects, Environment . Georg Thieme Verlag, 2002, ISBN 978-3-13-108972-4 , p. 256 ( limited preview in Google Book Search).
6. ↑ Lexicon of Medicinal Plants and Drugs: Chelerythrine - Lexicon of Medicinal Plants and Drugs , accessed on July 2, 2019.
7. ↑ Rudolf Hänsel, Konstantin Keller, Horst Rimpler, Georg Schneider: Hager's handbook of pharmaceutical practice, drugs E-O . Springer-Verlag, 2013, ISBN 978-3-642-57993-6 , pp. 111 ( limited preview in Google Book search).
8. ↑ R. Hegnauer: Chemotaxonomie der Pflanzen An overview of the distribution and the systematic importance of plant substances . Springer-Verlag, 2013, ISBN 978-3-0348-7985-9 , pp. 276 ( limited preview in Google Book search).
9. ^ Sanguinarine, a new organic alkali in Sanguinaria canadiensis . From Dana. In: Philipp Lorenz Geiger (Hrsg.): Magazine for pharmacy and the sciences involved . 6th year (1828) Volume XXIII, p. 124 (digitized version)
10. ↑ Dr. Probst. Description and method of representation of some of the substances newly discovered during the analysis of Chelidonium majus . In: Annalen der Pharmacie , Volume XXIX (1839), pp. 113–131, here: pp. 120–123 (digitized version ) --- Description and method of representation of some peculiar substances found during the investigation of the Glaucium luteum, as a material contribution to a comparative one Analysis of the Papaveraceae . In: Annalen der Pharmacie , Volume XXXI (1839), pp. 241–258, here: pp. 250–254 (digitized version )
11. ↑ Squint. About the Sanguinarin . In: Annals of Chemistry and Pharmacy . Volume XLIII (1842), pp. 233-236 (digitized version ) --- Sanguinarine identical to chelerythrine . In: Journal for practical chemistry . Volume LXVII (1856), p. 61 (digitized version)
12. ↑ Ludwig Weyland. Comparative studies on veratrine, sabadillin, dolphinine, emetine, aconitine, sanguinarine and potassium chloride . Brühl, Giessen 1869 (Inaug. Diss.). P. 18–19 and P. 31–34: Sanguinarin (digitized version )
13. ↑ M. Chastaing. Chimie organique. Alcaloïdes naturels. Chélérythrine . In: Edmond Frémy (ed.). Encyclopédie chimique . Volume VIII. Dunod, Paris 1885, pp. 172–176 (digitized version )
14. ↑ August Husemann and Theodor Husemann : The plant substances in chemical, physiological, pharmacological and toxicological terms. For doctors, pharmacists, chemists and pharmacologists. Springer, Berlin 1871, pp. 199-202: Chelerythrine. Sanguinarin. (Digitized version)
15. ^ Theodor Husemann. Handbook of the entire pharmacology. Springer, Berlin, 2nd edition, Volume II (1883), pp. 839–840 (digitized version )
16. ↑ Atta-ur- Rahman: Studies in Natural Products Chemistry Bioactive Natural Products, Part H . Elsevier, 2002, ISBN 978-0-08-052785-7 , pp. 158 ( limited preview in Google Book search).