Sanguinarin

Structural formula
	Illustration of the Sanguinarin cation
General
Surname	Sanguinarin
other names	Pseudochelerythrine
Molecular formula	C 20 H 15 NO 5 (hydroxide); C 20 H 14 ClNO 4 (chloride);
Brief description	orange needles (chloride)
External identifiers / databases
ECHA InfoCard	100.017.731
PubChem	5154
Wikidata	Q347392
properties
Molar mass	349.42 g mol −1 (hydroxide); 367.79 g mol −1 (chloride);
Physical state	firmly
Melting point	210–211 ° C (hydroxide); 277–280 ° C (chloride);
solubility	soluble in water
safety instructions
GHS labeling of hazardous substances danger
H and P phrases	H: 301
	P: 280-301 + 310
Toxicological data	1660 mg kg −1 ( LD 50 , rat , oral ) ; 19.4 mg kg −1 ( LD 50 , mouse , iv ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Sanguinarine is a quaternary ammonium compound from the group of isoquinoline - alkaloids , which as the hydroxide or chloride in many poppy plants ( Papaveraceae ), diamond plants ( Rutaceae ) and Erdrauchgewächsen ( Fumariaceae ), about celandine , Mexican Argemone , yellow horn poppy , White spring poppies and the Canadian bloodroot ( Sanguinaria canadensis ) occurs.

Sanguinarine is toxic by overriding the sodium-potassium pump .

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 or 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.

use

Sanguinarine is used as a natural bactericide in dentistry.

Individual evidence

↑ ^a ^b ^c ^d Entry on Sanguinarin. In: Römpp Online . Georg Thieme Verlag, accessed on May 15, 2013.

↑ ^a ^b ^c data sheet sanguinarine nitrate rotichrome (PDF) from Carl Roth , accessed on May 8, 2013.

^ Toxicologist. Vol. 5, p. 176, 1985.

↑ ^a ^b Entry on sanguinarine in the ChemIDplus database of the United States National Library of Medicine (NLM) .

↑ Farmakologiya i Toksikologiya. Vol. 29, p. 76, 1966.

↑ Heinrich Naschold: About the Sanguinarin, its properties and its composition . Fischer & Wittig, 1869 ( full text in the Google book search - Inaug. Diss).

^ 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)

↑ 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 )

↑ 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)

↑ 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 )

↑ M. Chastaing. Chimie organique. Alcaloïdes naturels. Chélérythrine . In: Edmond Frémy (ed.). Encyclopédie chimique . Volume VIII. Dunod, Paris 1885, pp. 172–176 (digitized version )

↑ 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)

^ Theodor Husemann. Handbook of the entire pharmacology. Springer, Berlin, 2nd edition, Volume II (1883), pp. 839–840 (digitized version )

↑ 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).

↑ Entry in the dental dictionary

[römpp-1] Entry on Sanguinarin. In: Römpp Online . Georg Thieme Verlag, accessed on May 15, 2013.

[cr-2] ta sheet sanguinarine nitrate rotichrome (PDF) from Carl Roth , accessed on May 8, 2013.

[3] Toxicologist. Vol. 5, p. 176, 1985.

[chemid-4] Entry on sanguinarine in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[5] Farmakologiya i Toksikologiya. Vol. 29, p. 76, 1966.

[6] Heinrich Naschold: About the Sanguinarin, its properties and its composition . Fischer & Wittig, 1869 ( full text in the Google book search - Inaug. Diss).

[7] 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)