Brucine

Brucine

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IUPACName=
OtherNames=2,3-Dimethoxystrychnine
10,11-Dimethoxystrychnine
Section1= Chembox Identifiers
CASNo=357-57-3
PubChem=442021
SMILES=COC1=C(C=C2C(=C1) [C@] 34C CN5 [C@H] 3C [C@@H] 6 [C@@H] 7 [C@@H] 4N2C(=O)C [C@@H] 7OCC=C6C5)OC
Section2= Chembox Properties
C=23|H=26|N=2|O=4
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Section3= Chembox Hazards
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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 milligrams of pure brucine will almost certainly suffer symptoms resembling strychnine poisoning.

Medically, 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 crystallise 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-crystallisation of brucine, whereas strychnine was shown to crystallise 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, ageing hitman Arthur Bishop (Bronson), using a celebratory glass of wine spiked with brucine, leaving Bishop to die of an apparent heart attack.

References


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Look at other dictionaries:

  • Brucine — Structure Général Synonymes 2,3 diméthoxy strychnine No CAS …   Wikipédia en Français

  • brucine — [ brysin ] n. f. • 1819; du lat. brucea, anc. nom d un arbuste abyssin découvert par J. Bruce ♦ Biochim. Alcaloïde voisin de la strychnine, extrait de la noix vomique. ● brucine nom féminin (de J. Bruce, nom propre) Alcaloïde extrait de la noix… …   Encyclopédie Universelle

  • Brucine — Bru cine, n. [Cf. F. brucine, fr. James Bruce, a Scottish traveler.] (Chem.) 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… …   The Collaborative International Dictionary of English

  • brucine — [bro͞o′sēn΄, bro͞o′sin] n. [after J. Bruce (1730 94), Scot explorer] a bitter, poisonous alkaloid, C23H26N2O4, found in seeds of nux vomica and other related plants: used as a lubricant additive and, in medicine, as a local anesthetic …   English World dictionary

  • brucine — An alkaloid from Strychnos nux vomica and S. ignatii (family Loganiaceae), that produces paralysis of sensory nerves and peripheral motor nerves; the convulsive action which is characteristic of strychnine is almost entirely absent; formerly used …   Medical dictionary

  • brucine — (bru si n ) s. f. Terme de chimie. Nom d un alcaloïde qu on nomme présentement vomicine (voy. vomicine). ÉTYMOLOGIE    Brucée (brucea antidysenterica), d où on croyait à tort que provenait la fausse angusture, qui fournit la brucine …   Dictionnaire de la Langue Française d'Émile Littré

  • brucine — brucinas statusas T sritis chemija apibrėžtis Alkaloidas. formulė C₂₃H₂₆N₂O₄ atitikmenys: angl. brucine rus. бруцин ryšiai: sinonimas – 2,3 dimetoksistrichninas …   Chemijos terminų aiškinamasis žodynas

  • brucine — noun Etymology: probably from French, from New Latin Brucea, genus name of Brucea antidysenterica, a shrub Date: 1823 a poisonous alkaloid C23H26N2O4 found with strychnine especially in nux vomica …   New Collegiate Dictionary

  • brucine — /brooh seen, sin/, n. Chem. a white, crystalline, bitter, slightly water soluble, very poisonous alkaloid, C23H26N2O4, obtained from the nux vomica tree Strychnos nux vomica, and from other species of the same genus, resembling but not as… …   Universalium

  • brucine — noun An alkaloid, related to strychnine, found in nux vomica …   Wiktionary

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