Brucine

From Wikipedia, the free encyclopedia
  (Redirected from Brucin)
Jump to: navigation, search
Brucine
Brucine2.svg
Identifiers
CAS number 357-57-3 YesY
PubChem 442021
ChemSpider 390579 YesY
UNII 6NG17YCK6H YesY
KEGG C09084 YesY
ChEMBL CHEMBL501756 YesY
IUPHAR ligand 342
Jmol-3D images Image 1
Properties
Molecular formula C23H26N2O4
Molar mass 394.46 g mol−1
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)
 YesY (verify) (what is: YesY/N?)
Infobox references

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.

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 (LD50 (rats, oral) 1 mg/kg, LD50 (rabbit, oral) 4 mg/kg).[citation needed] The probable fatal dose in adults is estimated at 1 gram.[1][full citation needed][2] Another source gives the minimal lethal dose in humans as 30 mg.[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,[which?] 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.[clarification needed][citation needed] Brucine and strychnine are basic and thus have a tendency to crystallize with acids; protonation of brucine is at the N(2) position.[clarification needed][citation needed] The ability of brucine, and to a lesser extent strychnine, to function as resolving agents for amino acids was reported by Fisher in 1899.[citation needed] The formation of diastereomeric brucine salts has been reported for thousands of organic compounds.[citation needed]

A solution of brucine in concentrated sulfuric acid can be used to test for nitrates and nitric acid giving a red color.[further explanation needed][citation needed]

Cultural references[edit]

Perhaps the best-known cultural reference to brucine occurs in The Count of Monte Cristo,[original research?] the novel by French author Alexandre Dumas, père, in a discussion of mithridatism:[this quote needs a citation]

"'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.'"

[original research?][this quote needs a citation] Brucine was also mentioned in the 1972 movie The Mechanic starring Charles Bronson,[original research?] 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.[citation needed]

References[edit]

  1. ^ Gosselin, 1984[full citation needed]
  2. ^ Arlina Borges, "Brucine - 7.2.1.1 Adults" International Programme on Chemical Safety (IPCS), Canadian Centre for Occupational Health and Safety (CCOHS), April 1990.
  3. ^ M. Wink and B.-E. van Wyk (2008) Mind-altering and Poisonous Plants of the World, p. 221, Portland: Timber Press.
  4. ^ Ari M. P. Koskinen (2012) Asymmetric Synthesis of Natural Products, 2nd Ed., New York:John Wiley & Sons, , pp. 17, 28-29, ISBN 1118347331, see [1], accessed 1 July 2014.

External links[edit]