Vomicine

a crystalline alkaloid C22H24N2O4 occurring with brucine and strychnine

//An alternative spelling for "Brucine"//: A powerful vegetable alkaloid, found, associated with strychnine, in the seeds of different species of Strychnos, especially in the Nux vomica. It is less powerful than strychnine. Called also brucia and brucina.
 * 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][|]] 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 hydrogens. 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. Vomicine (left) is a poisonous molecule that gets its name from the nut // Nux Vomica //, which is the seed of a tree found on the coasts of the East Indies. The seeds are sometimes called 'Quaker buttons', and are a source of strychnine as well as the emetic vomicine