| Brucine | |
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2,3-dimethoxystrychnidin-10-one |
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Other names
2,3-Dimethoxystrychnine |
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| Identifiers | |
| CAS number | 357-57-3 |
| PubChem | 442021 |
| ChemSpider | 390579 |
| UNII | 6NG17YCK6H |
| KEGG | C09084 |
| ChEMBL | CHEMBL501756 |
| IUPHAR ligand | 342 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C23H26N2O4 |
| Molar mass | 394.46 g mol−1 |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| 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). The probable fatal dose in adults is estimated at 1 gram.[1][2]
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 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.
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:
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.
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