Brucine

Title: Brucine
CAS Registry Number: 357-57-3
CAS Name: 2,3-Dimethoxystrychnidin-10-one
Additional Names: 10,11-dimethoxystrychnine
Molecular Formula: C23H26N2O4
Molecular Weight: 394.46
Percent Composition: C 70.03%, H 6.64%, N 7.10%, O 16.22%
Literature References: Toxic alkaloid resembling strychnine. Isoln from Strychnos seeds (Strychnos nux-vomica L. and S. ignatii Berg., Loganiaceae): C. Hartwick, P. Geiger, Arch. Pharm. 239, 491 (1901). Prepn from strychnine, q.v.: E. Tedeschi et al., Tetrahedron 24, 4573 (1968). 13C-NMR study: E. Wenkert et al., J. Org. Chem. 43, 1099 (1978). Electrophoretic determn in seeds: Y.-Y. Zong, C. Che, Planta Med. 61, 456 (1995). Toxicity data: M. H. Malone et al., J. Ethnopharmacol. 35, 295 (1992). Use as reagent for sulfur compounds: M. K. Tummuru et al., Analyst 109, 1105 (1984); for nitrates: J. Masini et al., Anal. Chem. 69, 1077 (1997). Review of structural elucidation: H. L. Holmes, Elucidation of the Structure of Strychnine and Brucine in The Alkaloids vol. I, R. H. F. Manske, Ed. (Academic Press, New York, 1950) pp 377-420.
Properties: Needles from acetone + water, mp 178°. [a]D -127° (chloroform), -85° (in abs alcohol). uv max (ethanol): 263, 301 nm (log e 4.09, 3.93).
Melting point: mp 178°
Optical Rotation: [a]D -127° (chloroform), -85° (in abs alcohol)
Absorption maximum: uv max (ethanol): 263, 301 nm (log e 4.09, 3.93)
Derivative Type: Tetrahydrate
Properties: Monoclinic prisms. Also forms a dihydrate. Very bitter taste. Bitterness threshold 1:220,000. Very poisonous! Handle dry powder in hood only. Becomes anhydr at 100°. One gram dissolves in 0.8 ml methanol, 1.3 ml alcohol, 5 ml chloroform, 25 ml ethyl acetate, 36 ml glycerol, about 100 ml benzene, 187 ml ether, 1320 ml water, 750 ml boiling water. pH of satd water soln 9.5. pK1 6.04, pK2 11.7. LD50 in mice (mg/kg): 12.0 i.v.; 62.0 i.p.; 150.0 orally (Malone).
pKa: pK1 6.04, pK2 11.7
Toxicity data: LD50 in mice (mg/kg): 12.0 i.v.; 62.0 i.p.; 150.0 orally (Malone)
Use: Denaturing alcohol and oils; in analytical chemistry; for separating racemic mixtures. Addition agent to lubricants.
Therap-Cat: CNS stimulant.
Keywords: CNS Stimulant.
Bryostatins Bucetin Buchu Bucillamine Bucindolol

Brucine
Brucine.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
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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.