Molecular formula C
23H 26N 2O 4
Molar mass 394.46 g mol
Melting point 178 °C (352 °F; 451 K)
Except where noted otherwise, data are given for materials in their
standard state (at 25 °C (77 °F), 100 kPa)
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This article needs attention from an expert in Chemistry or Medicine. The specific problem is: poor medical and toxicology converage, and all but total omission of major chemistry uses of brucine, with significant detail on lesser matters. (July 2014)
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Brucine is a bitter alkaloid closely related to strychnine. It occurs in several plant species, the most well known being the tree, found in South-East Asia. Strychnos nux-vomica
Toxicity [ edit ]
While brucine is related to strychnine, it is not as poisonous. Nevertheless, a human consuming over 2 mg of pure brucine will almost certainly suffer symptoms resembling strychnine poisoning (
LD (rats, oral) 1 mg/kg, LD 50 50 (rabbit, oral) 4 mg/kg). The probable fatal dose in adults is estimated at 1 gram. [1 ] Another source gives the minimal lethal dose in humans as 30 mg. [2 ] [3 ]
Medical uses [ edit ]
For medicinal purposes, brucine is primarily used in the regulation of high blood pressure and other comparatively benign cardiac ailments. It is derived from cultivated plants,
commercially, in some parts of the United States and European Union.
Chemistry [ edit ]
Brucine sees use in
asymmetric synthesis, and was, in fact, the first natural product used as an organocatalyst in a reaction resulting in a successful enantiomeric enrichment (i.e., by Marckwald in 1904). [4 ]
The alkaloid brucine is similar in structure to
strychnine, with methoxy groups rather than hydrogen atoms at positions 9 and 10 on the aromatic ring. Brucine and strychnine are basic and thus have a tendency to crystallize with acids; protonation of brucine is at the N(2) position. The ability of brucine, and to a lesser extent strychnine, to function as resolving agents for amino acids was reported by Fisher in 1899. The formation of diastereomeric brucine salts has been reported for thousands of organic compounds.
A solution of brucine in concentrated sulfuric acid can be used to test for nitrates and nitric acid giving a red color.
Cultural references [ edit ]
Perhaps the best-known cultural reference to brucine occurs in
, the novel by French author The Count of Monte Cristo Alexandre Dumas, père, in a discussion of mithridatism:
"'Well,' replied Monte Cristo, 'suppose, then, that this poison was brucine, and you were to take a milligramme the first day, two milligrammes the second day, and so on.'"
starring The Mechanic Charles Bronson, in which the young hitman Steve McKenna ( Jan-Michael Vincent) betrays his mentor, aging hitman Arthur Bishop (Bronson), using a celebratory glass of wine spiked with brucine, leaving Bishop to die of an apparent heart attack.
Brucine was also mentioned in the 1972 movie
References [ edit ]
^ Gosselin, 1984
^ Arlina Borges, "Brucine - 126.96.36.199 Adults" International Programme on Chemical Safety (IPCS), Canadian Centre for Occupational Health and Safety (CCOHS), April 1990.
^ M. Wink and B.-E. van Wyk (2008) Mind-altering and Poisonous Plants of the World, p. 221, Portland: Timber Press.
^ Ari M. P. Koskinen (2012) Asymmetric Synthesis of Natural Products, 2nd Ed., New York:John Wiley & Sons, , pp. 17, 28-29, ISBN 1118347331, see , accessed 1 July 2014.
External links [ edit ]