3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||394.471 g·mol−1|
|Melting point||178 °C (352 °F; 451 K)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Brucine, an alkaloid closely related to strychnine, is most commonly found in the Strychnos nux-vomica tree. Brucine poisoning is rare, since it is usually ingested with strychnine, and strychnine is more toxic than brucine. In synthetic chemistry, it can be used as a tool for stereospecific chemical syntheses.
Brucine was discovered in 1819 by Pelletier and Caventou in the bark of the Strychnos nux-vomica tree. While its structure was not deduced until much later, it was determined that it was closely related to strychnine in 1884, when the chemist Hanssen converted both strychnine and brucine into the same molecule.
Since brucine is a large chiral molecule, it has been used in chiral resolution. Fisher first reported its use as a resolving agent in 1899, and it was the first natural product used as an organocatalyst in a reaction resulting in a enantiomeric enrichment by Marckwald, in 1904. Its bromide salt has been used as the stationary phase in HPLC in order to selectively bind one of two anionic enantiomers. Brucine has also been used in fractional distillation in acetone in order to resolve dihydroxy fatty acids, as well as diarylcarbinols.
“Well, suppose, then, that this poison was brucine, and you were to take a milligramme the first day, two milligrams the second day, and so on…at the end of a month, when drinking water from the same carafe, you would kill the person who drank with you, without your perceiving…that there was any poisonous substance mingled with this water.”
Brucine in also mentioned in the 1972 version of The Mechanic, in which the hitman Steve McKenna betrays his mentor, aging hitman Arthur Bishop, using a celebratory glass of wine spiked with brucine, leaving Bishop to die of an apparent heart attack.
Brucine intoxication occurs very rarely, since it is usually ingested with strychnine. Symptoms of brucine intoxication include muscle spasms, convulsions, rhabdomyolysis, and acute renal failure. Brucine’s mechanism of action closely resembles that of strychnine. It acts as an antagonist at glycine receptors and paralyzes inhibitory neurons.
The probable fatal dose of brucine in adults is 1 g. In other animals, the LD50 varies considerably.
|Animal||Route of Entry||LD50|
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|Wikisource has the text of the 1911 Encyclopædia Britannica article Brucine.|
- Brucine, INCHEM.org