Brucine is an alkaloid closely related to strychnine, most commonly found in the Strychnos nux-vomica tree. Brucine poisoning is rare, since it is usually ingested with strychnine, and strychnine is more Toxicity than brucine. In chemical synthesis, it can be used as a tool for stereospecific chemical syntheses.
Brucine's name derives from this of the genus Brucea, named after James Bruce who brought back Brucea antidysenterica from Ethiopia.
History
Brucine was discovered in 1819 by the French chemist Pelletier and the French pharmacist Caventou in the bark of the
Strychnos nux-vomica tree.
While its chemical 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.
Identification
Brucine can be detected and quantified using liquid chromatography-mass spectrometry.
Historically, brucine was distinguished from strychnine by its reactivity toward
chromic acid.
Applications
Chemical applications
Since brucine is a large
Chirality 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 an
Enantiomer enrichment by Marckwald, in 1904.
Its bromide salt has been used as the stationary phase in
HPLC to selectively bind one of two an
enantiomers.
Brucine has also been used for fractional crystallization in
acetone to resolve dihydroxy
fatty acids,
as well as di
Aryl group.
If formic acid is added to a mixture of brucine and potassium nitrate, its color instantly turns red. This reaction has been used for the direct colorimetric detection of
.
Medical applications
While brucine has been shown to have good
Chemotherapy effects, on both hepatocellular carcinoma
and
breast cancer,
its narrow therapeutic window has limited its use as a treatment for
cancer.
Brucine is also used in traditional Chinese medicine as an anti-inflammatory and analgesic agent,
Alcohol denaturant
Brucine is one of the many chemicals used as a denaturant to make
ethanol unfit for human consumption.
Cultural references
One of the most famous cultural references to brucine occurs in
The Count of Monte Cristo, the novel by French author
Alexandre Dumas. In a discussion of
mithridatism, Monte Cristo states:
“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 is also mentioned in the 1972 version of The Mechanic, in which the hitman Steve McKenna betrays his mentor, ageing hitman Arthur Bishop, using a celebratory glass of wine spiked with brucine, leaving Bishop to die of an apparent heart attack.
Such fictions run contrary to reality in the very properties which make brucine useful as a denaturant, and useless as a covert poison. While being only about one-eighth as toxic as strychnine, its threshold of bitterness occurs at 69 % greater dilution. A drink laden with brucine, overwhelmingly bitter at far below Lethal dose, would cause an intended victim to gag on the first sip.
Safety
Brucine intoxication occurs very rarely, since it is usually ingested with strychnine. Symptoms of brucine intoxication include muscle
,
,
rhabdomyolysis, and acute kidney injury. Brucine’s mechanism of action closely resembles that of strychnine. It acts as an
antagonist at
and paralyzes
Neurotransmitter.
The probable lethal dose of brucine in adults is 1 g.
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