Brucine

Structural formula
General
Surname	Brucine
other names	2,3-dimethoxystrychnine; 10,11-dimethoxystrychnine; (-) - Brucine;
Molecular formula	C 23 H 26 N 2 O 4
Brief description	white, crystalline solid
External identifiers / databases
EC number	206-614-7
ECHA InfoCard	100.006.014
PubChem	442021
Wikidata	Q411022
properties
Molar mass	394.47 g mol −1
Physical state	firmly
Melting point	178 ° C
solubility	poor in water (3.2 g l −1 at 15 ° C)
safety instructions
GHS hazard labeling from Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger
H and P phrases	H: 300 + 330-412
	P: 273-304 + 340-309 + 310
Toxicological data	150 mg kg −1 ( LD 50 , mouse , oral ) ; 60 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 .

Brucine [ brut͡siːn ] (after the Scottish scientist James Bruce ) is a highly toxic alkaloid which in the seeds of ordinary Brechnuss and strychnos ignatii occurs. It belongs to the group of the Strychnos alkaloids .

Poisonous effect

Brucine acts already in small amounts as a neurotoxin . There is a risk of poisoning not only if swallowed, but also if inhaled and in contact with the skin. The consequences are pulmonary edema and central respiratory paralysis. Heart, kidney and liver patients are particularly at risk. The oral lethal dose for a rat is given as 1 mg kg ⁻¹ .

properties

Brucine is very similar to strychnine and, like strychnine, occurs naturally in neaf nuts. Chemically include both connections to the Hydrocarbazol - alkaloids . Brucine has a very bitter taste; the taste is still perceptible in an aqueous solution at a dilution of 1: 220,000.

Analytics

The reliable qualitative and quantitative detection of brucine is possible with chromatographic methods. The thin layer chromatography is however rarely used and is usually only in the presence of relatively high concentrations. Sufficient sample preparation steps are essential for the analysis of complex specimens such as urine or blood serum . The method most frequently used today is the coupling of HPLC with mass spectrometry , with which the brucine metabolites can also be recorded. These procedures are also suitable for use in forensics .

use

Brucine finds u. a. Use in analytics. This is how it reacts in conc. Sulfuric acid with nitrate ions to form a red to red-orange colored compound, the composition of which is unknown.

Individual evidence

↑ ^a ^b ^c ^d ^e Entry on brucine in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
↑ Entry on Brucine 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 .
↑ ^a ^b Entry on brucine in the ChemIDplus database of the United States National Library of Medicine (NLM) .
↑ Entry on brucine. In: Römpp Online . Georg Thieme Verlag, accessed on April 19, 2014.
↑ K. Dhalwal, VM Shinde, AG Namdeo, KR Mahadik, SS Kadam: Development and validation of a TLC-densitometric method for the simultaneous quantitation of strychnine and brucine from Strychnos spp. and its formulations. In: Journal of Chromatographic Science . 45 (10), 2007, pp. 706-709, PMID 18078581 .
↑ X. Liu, S. Zheng, Z. Jiang, C. Liang, R. Wang, Z. Zhou, Y. Zhang, Y. Yu: Rapid separation and identification of Strychnos alkaloids metabolites in rats by ultra high performance liquid chromatography with linear ion trap Orbitrap mass spectrometry. In: Journal of Separation Science . 37 (7), 2014, pp. 764-774. PMID 24812693 .
↑ X. Chen, Y. Lai, Z. Cai: Simultaneous analysis of strychnine and brucine and their major metabolites by liquid chromatography-electrospray ion trap mass spectrometry. In: Journal of Analytical Toxicology . 36 (3), 2012, pp. 171-176. PMID 22417832 .
^ J. Teske, JP Weller, UV Albrecht, A. Fieguth: Fatal intoxication due to brucine. In: Journal of Analytical Toxicology. 35 (4), 2011, pp. 248-253. PMID 21513620 .
↑ Gerhart Jander, Ewald Blasius: Textbook of analytical and preparative inorganic chemistry. 12th edition. S. Hirzel Verlag, Stuttgart 1983, ISBN 3-7776-0379-1 , p. 441.

[GESTIS-1] Entry on brucine in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .

[CLP_100.006.014-2] Entry on Brucine 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 .

[ChemIDplus-3] Entry on brucine in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[roempp-4] Entry on brucine. In: Römpp Online . Georg Thieme Verlag, accessed on April 19, 2014.

[5] K. Dhalwal, VM Shinde, AG Namdeo, KR Mahadik, SS Kadam: Development and validation of a TLC-densitometric method for the simultaneous quantitation of strychnine and brucine from Strychnos spp. and its formulations. In: Journal of Chromatographic Science . 45 (10), 2007, pp. 706-709, PMID 18078581 .

[6] X. Liu, S. Zheng, Z. Jiang, C. Liang, R. Wang, Z. Zhou, Y. Zhang, Y. Yu: Rapid separation and identification of Strychnos alkaloids metabolites in rats by ultra high performance liquid chromatography with linear ion trap Orbitrap mass spectrometry. In: Journal of Separation Science . 37 (7), 2014, pp. 764-774. PMID 24812693 .

[7] X. Chen, Y. Lai, Z. Cai: Simultaneous analysis of strychnine and brucine and their major metabolites by liquid chromatography-electrospray ion trap mass spectrometry. In: Journal of Analytical Toxicology . 36 (3), 2012, pp. 171-176. PMID 22417832 .

[8] J. Teske, JP Weller, UV Albrecht, A. Fieguth: Fatal intoxication due to brucine. In: Journal of Analytical Toxicology. 35 (4), 2011, pp. 248-253. PMID 21513620 .

[9] Gerhart Jander, Ewald Blasius: Textbook of analytical and preparative inorganic chemistry. 12th edition. S. Hirzel Verlag, Stuttgart 1983, ISBN 3-7776-0379-1 , p. 441.