Brucine
| Brucine | |
|---|---|
 | |
| IUPAC name 2,3-dimethoxystrychnidin-10-one | |
| Other names 2,3-Dimethoxystrychnine | |
| Identifiers | |
| CAS number | 357-57-3  |
| PubChem | 442021 |
| ChemSpider | 390579 |
| UNII | 6NG17YCK6H |
| KEGG | C09084 |
| ChEMBL | CHEMBL501756 |
| IUPHAR ligand | 342 |
| Jmol-3D images | {{#if:O=C7N2c1cc(OC)c(OC)cc1[C@@]64[C@@H]2[C@@H]3[C@@H](OC/C=C5\[C@@H]3C[C@@H]6N(CC4)C5)C7|Image 1 |
| |
| |
| Properties | |
| Molecular formula | C23H26N2O4 |
| Molar mass | 394.46 g mol−1 |
| Melting point | 178 °C; 352 °F; 451 K |
(verify) (what is: / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
| 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.
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][2] Another source gives the minimal lethal dose in humans as 30 mg.[3]
A solution of brucine in concentrated sulfuric acid can be used to test for nitrates and nitric acid giving a red color.
For medicinal purposes, brucine is primarily used in the regulation of high blood pressure and other comparatively benign cardiac ailments. It (which plant?) is cultivated commercially in some parts of the United States and European Union.
The alkaloid brucine is isostructural to strychnine, but with methoxy groups at positions 9 and 10 on the aromatic ring rather than hydrogen atoms. Both brucine and strychnine are commonly used as agents for chiral resolution, the separation of racemic mixtures. 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 diastereomeric 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 Cristo, the novel by French author Alexandre Dumas, père, in a discussion of mithridatism:
- "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, 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.
References
- ↑ Gosselin, 1984
- ↑ Arlina Borges, "Brucine - 7.2.1.1 Adults" International Programme on Chemical Safety (IPCS), Canadian Centre for Occupational Health and Safety (CCOHS), April 1990.
- ↑ M. Wink and B.-E. van Wyk (2008), Mind-altering and Poisonous Plants of the World, p.221, Portland: Timber Press.
External links
 |
Wikisource has the text of the 1911 Encyclopædia Britannica article Brucine. |
- Brucine, INCHEM.org
| ||||||||||||||||||||||||||||||||||||||||||||||