Aconitine

Structural formula
General
Surname	Aconitine
other names	Aconite
Molecular formula	C 34 H 47 NO 11
Brief description	light yellow solid which crystallizes in hexagonal plates
External identifiers / databases
EC number	206-121-7
ECHA InfoCard	100.005.566
PubChem	245005
Wikidata	Q342108
properties
Molar mass	645.72 g mol −1
Physical state	firmly
Melting point	204 ° C
pK s value	5.88
solubility	very good in dilute acids and chloroform ; little in water (0.3 g l −1 ) and ethanol (35 g l −1 );
safety instructions
GHS hazard labeling from Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger
H and P phrases	H: 300 + 330
	P: 301 + 310 + 330-304 + 340 + 310
Toxicological data	0.166 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 .

Aconitine or aconitine is a diterpene alkaloid that is derived from aconane . Aconitine can be hydrolyzed to benzoylaconine and aconine .

Occurrence

Aconitum napellus subsp. vulgare in Andorra

Aconitine is the main alkaloid in all Aconitum species, including the monkshood . Aconitine is found in all parts of the plant. The discovery and first isolation is attributed to the Heidelberg pharmacist Philipp Lorenz Geiger .

Analytics

The specific rotation is [α] _D + 17.3 ° when it was dissolved in chloroform . The detection takes place via Dragendorff reagent , in which an orange color reaction can be observed.

The reliable qualitative and quantitative determination of aconitine succeeds after adequate sample preparation by using the coupling of HPLC with mass spectrometry

effect

Aconitine is considered to be one of the most powerful plant poisons ever; it is more effective than strychnine . Aconitine and related alkaloids are absorbed very quickly intestinally , but also through intact skin and mucous membranes . Aconitine slows the inactivation of the voltage-gated sodium channel and thereby prolongs the influx of sodium ions during the action potential. It has a peripheral and central effect on motor and sensory nerves, initially stimulating, followed by paralysis. The main cardiac effects are arrhythmias and bradycardia , which leads to diastolic cardiac arrest at a lethal dose .

The lethal dose of aconitine for an adult is around 5 milligrams. That is why it - in the form of the blue iron hat - was previously used as arrow , bait - and murder poison.

Aconitine requires a prescription . It is still used in homeopathic doses for rheumatism and colds. Aconitine is only available without a prescription from the D4 potency (which corresponds to a dilution of 1: 10,000). In combination preparations, lower potencies are also used in small individual quantities.

Individual evidence

↑ ^a ^b Data sheet Aconitine from Sigma-Aldrich , accessed on June 15, 2011 ( PDF ).
↑ Entry on aconitine. In: Römpp Online . Georg Thieme Verlag, accessed on July 16, 2014.
↑ ^a ^b ^c Entry on aconitine in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
^ ^A ^b ^c F. von Bruchhausen, S. Ebel, AW Frahm, E. Hackenthal: Hagers Handbook of Pharmaceutical Practice. Volume 7: Fabrics A – D. 5th edition. Birkhäuser / Springer, 1991, ISBN 3-540-52688-9 , p. 63.
↑ Entry on Aconitine in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
^ Geiger, Philipp Lorenz. In: Edward Kremers, George Urdang, Glenn Sonnedecker: Kremers and Urdang's History of Pharmacy. American Institute of the History of Pharmacy, Madison WI 1986, ISBN 0-931292-17-4 , p. 459.
↑ SW Ng, CK Ching, AY Chan, TW Mak: Simultaneous detection of 22 toxic plant alkaloids (aconitum alkaloids, solanaceous tropane alkaloids, sophora alkaloids, strychnos alkaloids and colchicine) in human urine and herbal samples using liquid chromatography-tandem mass spectrometry. In: J Chromatogr B Analyt Technol Biomed Life Sci. 942-943, Dec 30, 2013, pp. 63-69. PMID 24216273 .
^ J. Carlier, J. Guitton, L. Romeuf, F. Bévalot, B. Boyer, L. Fanton, Y. Gaillard: Screening approach by ultra-high performance liquid chromatography-tandem mass spectrometry for the blood quantification of thirty-four toxic principles of plant origin. Application to forensic toxicology. In: J Chromatogr B Analyt Technol Biomed Life Sci. 975, Jan 15, 2015, pp. 65-76. PMID 25438245 .

[sigma-1] Data sheet Aconitine from Sigma-Aldrich , accessed on June 15, 2011 ( PDF ).

[2] Entry on aconitine. In: Römpp Online . Georg Thieme Verlag, accessed on July 16, 2014.

[GESTIS-3] Entry on aconitine in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .

[hager-4] A ^b ^c F. von Bruchhausen, S. Ebel, AW Frahm, E. Hackenthal: Hagers Handbook of Pharmaceutical Practice. Volume 7: Fabrics A – D. 5th edition. Birkhäuser / Springer, 1991, ISBN 3-540-52688-9 , p. 63.

[CLP_100.005.566-5] Entry on Aconitine in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[Geiger-6] Geiger, Philipp Lorenz. In: Edward Kremers, George Urdang, Glenn Sonnedecker: Kremers and Urdang's History of Pharmacy. American Institute of the History of Pharmacy, Madison WI 1986, ISBN 0-931292-17-4 , p. 459.

[7] SW Ng, CK Ching, AY Chan, TW Mak: Simultaneous detection of 22 toxic plant alkaloids (aconitum alkaloids, solanaceous tropane alkaloids, sophora alkaloids, strychnos alkaloids and colchicine) in human urine and herbal samples using liquid chromatography-tandem mass spectrometry. In: J Chromatogr B Analyt Technol Biomed Life Sci. 942-943, Dec 30, 2013, pp. 63-69. PMID 24216273 .

[8] J. Carlier, J. Guitton, L. Romeuf, F. Bévalot, B. Boyer, L. Fanton, Y. Gaillard: Screening approach by ultra-high performance liquid chromatography-tandem mass spectrometry for the blood quantification of thirty-four toxic principles of plant origin. Application to forensic toxicology. In: J Chromatogr B Analyt Technol Biomed Life Sci. 975, Jan 15, 2015, pp. 65-76. PMID 25438245 .