Brucine is a bitter
alkaloidAlkaloids are naturally occurring chemical compounds containing basic nitrogen atoms. The name derives from the word alkaline and was used to describe any nitrogen-containing base. Alkaloids are produced by a large variety of organisms, including bacteria, fungi, plants, and animals and are part of...
closely related to
strychnineStrychnine is a very toxic , colorless crystalline alkaloid used as a pesticide, particularly for killing small vertebrates such as birds and rodents. Strychnine causes muscular convulsions and eventually death through asphyxia or sheer exhaustion. The most common source is from the seeds of the...
. It occurs in several plant species, the most well known being the
Strychnos nux-vomica tree, found in South-East Asia.
While brucine is related to strychnine, it is not as poisonous. Nevertheless, a human consuming over 2 milligrams of pure brucine will almost certainly suffer symptoms resembling strychnine poisoning.
For medicinal purposes, brucine is primarily used in the regulation of high blood pressure and other comparatively benign cardiac ailments.
Brucine is a bitter
alkaloidAlkaloids are naturally occurring chemical compounds containing basic nitrogen atoms. The name derives from the word alkaline and was used to describe any nitrogen-containing base. Alkaloids are produced by a large variety of organisms, including bacteria, fungi, plants, and animals and are part of...
closely related to
strychnineStrychnine is a very toxic , colorless crystalline alkaloid used as a pesticide, particularly for killing small vertebrates such as birds and rodents. Strychnine causes muscular convulsions and eventually death through asphyxia or sheer exhaustion. The most common source is from the seeds of the...
. It occurs in several plant species, the most well known being the
Strychnos nux-vomica tree, found in South-East Asia.
While brucine is related to strychnine, it is not as poisonous. Nevertheless, a human consuming over 2 milligrams of pure brucine will almost certainly suffer symptoms resembling strychnine poisoning.
For medicinal purposes, brucine is primarily used in the regulation of high blood pressure and other comparatively benign cardiac ailments. It is cultivated commercially in some parts of the United States and European Union.
The alkaloid brucine is isostructural to
strychnineStrychnine is a very toxic , colorless crystalline alkaloid used as a pesticide, particularly for killing small vertebrates such as birds and rodents. Strychnine causes muscular convulsions and eventually death through asphyxia or sheer exhaustion. The most common source is from the seeds of the...
, with methoxy groups at the aromatic ring rather than hydrogens (positions 9 and 10). Both brucine and strychnine are commonly used as agents for
chiral resolutionChiral resolution in stereochemistry is a process for the separation of racemic compounds into their enantiomers. It is an important tool in the production of optically active drugs...
. The separation of racemic mixtures by alkaloids from the cinchona bark has been known since 1853, when its use as such was reported by Pasteur. The ability of brucine, and to a lesser extent strychnine, to function as resolving agents for amino acids was reported by Fisher in 1899. Brucine and strychnine are basic and thus have a tendency to crystallise with acids. The acid-base reaction leaves the brucine protonated at the N(2) position. The formation of
diastereomerDiastereomers are stereoisomers that are not enantiomers . Diastereomers can have different physical properties and different reactivity...
ic salts has been reported for thousands of organic compounds. The packing of brucine in corrugated (waving) layers was an essential aspect in the co-crystallisation of brucine, whereas strychnine was shown to crystallise predominantly in bilayers.
Cultural references
Perhaps the best-known reference to brucine occurs in
The Count of Monte CristoThe Count of Monte Cristo is an adventure novel by Alexandre Dumas, père. It is often considered to be, along with The Three Musketeers, Dumas' most popular work. The writing of the work was completed in 1844...
, the novel by French author
Alexandre Dumas, pèreAlexandre Dumas, père, born Dumas Davy de la Pailleterie was a French writer, best known for his numerous historical novels of high adventure which have made him one of the most widely read French authors in the world...
, in a discussion of
mithridatismMithridatism is the practice of protecting oneself against a poison by gradually self-administering non-lethal amounts. The word derives from Mithridates VI, the King of Pontus, who so feared being poisoned that he regularly ingested small doses, aiming to develop immunity...
:
- "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."
Brucine was also mentioned in the 1972 movie
The MechanicThe Mechanic is a 1972 action thriller film, directed by Michael Winner. It stars Charles Bronson and Jan-Michael Vincent.The film is noted for its opening...
, starring
Charles BronsonCharles Bronson was an American actor best known for his "tough guy" image, who starred in such classic films as Once Upon a Time in the West, The Magnificent Seven, The Dirty Dozen, The Great Escape, The Evil That Men Do and the popular Death Wish series...
in which the young
hitmanA hitman usually is an assassin who is hired to assassinate a target via contract killing.- Hitmen in organized crime :Hitmen are largely linked to the world of organized crime. Hitmen are hired people, usually males who kill people for money. For notable examples see Murder, Inc...
Steve McKenna (
Jan-Michael VincentJan-Michael Vincent is an American actor best-known for his role as helicopter pilot Stringfellow Hawke on the 1980s U.S. television series Airwolf , which continues to enjoy a large cult fanbase...
) betrays his mentor, ageing hitman Arthur Bishop (Bronson), using a celebratory glass of wine spiked with brucine, leaving Bishop to die of an apparent heart attack.