Brucine
Encyclopedia
Brucine is a bitter alkaloid
closely related to strychnine
. 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 mg of pure brucine will almost certainly suffer symptoms resembling strychnine poisoning ( (rats, oral) 1 mg/kg, LD50 (rabbit, oral) 4 mg/kg). The probable fatal dose in adults is estimated at 1 gram.
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 strychnine
, 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 resolution
. 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 crystallize with acids. The acid-base reaction leaves the brucine protonated at the N(2) position. The formation of diastereomer
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-crystallization of brucine, whereas strychnine was shown to crystallize predominantly in bilayers.
, the novel by French author Alexandre Dumas, père
, in a discussion of mithridatism
:
Brucine was also mentioned in the 1972 movie The Mechanic
, starring 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.
Alkaloid
Alkaloids are a group of naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids...
closely related to strychnine
Strychnine
Strychnine is a highly 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...
. 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 mg of pure brucine will almost certainly suffer symptoms resembling strychnine poisoning ( (rats, oral) 1 mg/kg, LD50 (rabbit, oral) 4 mg/kg). The probable fatal dose in adults is estimated at 1 gram.
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 strychnine
Strychnine
Strychnine is a highly 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...
, 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 resolution
Chiral resolution
Chiral 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
Base (chemistry)
For the term in genetics, see base A base in chemistry is a substance that can accept hydrogen ions or more generally, donate electron pairs. A soluble base is referred to as an alkali if it contains and releases hydroxide ions quantitatively...
and thus have a tendency to crystallize with acids. The acid-base reaction leaves the brucine protonated at the N(2) position. The formation of diastereomer
Diastereomer
Diastereomers are stereoisomers that are not enantiomers.Diastereomerism occurs when two or more stereoisomers of a compound have different configurations at one or more of the equivalent stereocenters and are not mirror images of each other.When two diastereoisomers differ from each other at...
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-crystallization of brucine, whereas strychnine was shown to crystallize predominantly in bilayers.
Cultural references
Perhaps the best-known reference to brucine occurs in The Count of Monte CristoThe Count of Monte Cristo
The Count of Monte Cristo is an adventure novel by Alexandre Dumas. It is often considered to be, along with The Three Musketeers, Dumas's most popular work. He completed the work in 1844...
, the novel by French author Alexandre Dumas, père
Alexandre Dumas, père
Alexandre Dumas, , born Dumas Davy de la Pailleterie was a French writer, best known for his historical novels of high adventure which have made him one of the most widely read French authors in the world...
, in a discussion of mithridatism
Mithridatism
Mithridatism 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 Mechanic
The Mechanic
The Mechanic is a 1972 American action-thriller film directed by Michael Winner. It stars Charles Bronson and Jan-Michael Vincent.The film is noted for its opening...
, starring Charles Bronson
Charles Bronson
Charles Bronson , born Charles Dennis Buchinsky was an American actor, best-known for such films as Once Upon a Time in the West, The Magnificent Seven, The Dirty Dozen, The Great Escape, Rider on the Rain, The Mechanic, and the popular Death Wish series...
in which the young hitman
Hitman
A hitman is a person hired to kill another person.- Hitmen in organized crime :Hitmen are largely linked to the world of organized crime. Hitmen are hired people who kill people for money. Notable examples include Murder, Inc., Mafia hitmen and Richard Kuklinski.- Other cases involving hitmen...
Steve McKenna (Jan-Michael Vincent
Jan-Michael Vincent
Jan-Michael Vincent is an American actor best known for his role as helicopter pilot Stringfellow Hawke on the 1980s U.S. television series Airwolf .-Early life:...
) 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.
External links
- Brucine, INCHEM.org