Names | |
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IUPAC name 2,3-Dimethoxystrychnidin-10-one | |
Systematic IUPAC name (4bR,4b1S,7aS,8aR,8a1R,12aS)-2,3-Dimethoxy-4b1,5,6,7a,8,8a,8a1,11,12a,13-decahydro-14H-12-oxa-7,14a-diaza-7,9-methanocyclohepta[cd]cyclopenta[g]fluoranthen-14-one | |
Other names 2,3-Dimethoxystrychnine 10,11-Dimethoxystrychnine | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.006.014 |
EC Number |
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KEGG | |
PubChem CID | |
RTECS number |
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UNII | |
UN number | 1570 |
CompTox Dashboard (EPA) | |
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Properties | |
C23H26N2O4 | |
Molar mass | 394.471 g·mol−1 |
Melting point | 178 °C (352 °F; 451 K) |
Hazards | |
GHS labelling: | |
Danger | |
H300, H330, H412 | |
P260, P264, P270, P271, P273, P284, P301+P310, P304+P340, P310, P320, P321, P330, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Brucine is an alkaloid closely related to strychnine, most commonly found in the Strychnos nux-vomica tree. Brucine poisoning is rare, since it is usually ingested with strychnine, and strychnine is more toxic than brucine. In chemical synthesis, it can be used as a tool for stereospecific chemical syntheses.
Brucine's name derives from this of the genus Brucea , named after James Bruce who brought back Brucea antidysenterica from Ethiopia.
Brucine was discovered in 1819 by the French chemist Pelletier and the French pharmacist Caventou in the bark of the Strychnos nux-vomica tree. [1] While its chemical structure was not deduced until much later, it was determined that it was closely related to strychnine in 1884 when the chemist Hanssen converted both strychnine and brucine into the same molecule. [2]
Brucine can be detected and quantified using liquid chromatography-mass spectrometry. [3] Historically, brucine was distinguished from strychnine by its reactivity toward chromic acid. [4]
Since brucine is a large chiral molecule, it has been used in chiral resolution. Fisher first reported its use as a resolving agent in 1899, and it was the first natural product used as an organocatalyst in a reaction resulting in an enantiomeric enrichment by Marckwald, in 1904. [5] Its bromide salt has been used as the stationary phase in HPLC to selectively bind one of two anionic enantiomers. [6] Brucine has also been used for fractional crystallization in acetone to resolve dihydroxy fatty acids, [7] as well as diaryl carbinols. [8]
While brucine has been shown to have good anti-tumor effects, on both hepatocellular carcinoma [9] and breast cancer, [10] its narrow therapeutic window has limited its use as a treatment for cancer.
Brucine is also used in traditional Chinese medicine as an anti-inflammatory and analgesic agent, [11] as well as in some Ayurveda and homeopathy drugs. [12]
Brucine is one of the many chemicals used as a denaturant to make alcohol unfit for human consumption. [13]
One of the most famous cultural references to brucine occurs in The Count of Monte Cristo , the novel by French author Alexandre Dumas. In a discussion of mithridatism, Monte Cristo states:
“Well, suppose, then, that this poison was brucine, and you were to take a milligramme the first day, two milligrams the second day, and so on…at the end of a month, when drinking water from the same carafe, you would kill the person who drank with you, without your perceiving…that there was any poisonous substance mingled with this water.” [14]
Brucine is also mentioned in the 1972 version of The Mechanic , in which the hitman Steve McKenna betrays his mentor, ageing hitman Arthur Bishop, using a celebratory glass of wine spiked with brucine, leaving Bishop to die of an apparent heart attack. [15]
Such fictions run contrary to reality in the very properties which make brucine useful as a denaturant, and useless as a covert poison. While being only about one-eighth as toxic as strychnine, its threshold of bitterness occurs at 69 % greater dilution. A drink laden with brucine, overwhelmingly bitter at far below lethal concentration, would cause an intended victim to gag on the first sip.
Brucine intoxication occurs very rarely, since it is usually ingested with strychnine. Symptoms of brucine intoxication include muscle spasms, convulsions, rhabdomyolysis, and acute kidney injury. Brucine’s mechanism of action closely resembles that of strychnine. It acts as an antagonist at glycine receptors and paralyzes inhibitory neurons.
The probable lethal dose of brucine in adults is 1 g. [16] In other animals, the LD50 varies considerably.
Animal | Route of entry | LD50 [17] |
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Mouse | Subcutaneous | 60 mg/kg |
Rat | Intraperitoneal | 91 mg/kg |
Rabbit | Oral | 4 mg/kg |
Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar structure may also be termed alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen or sulfur. Rarer still, they may contain elements such as phosphorus, chlorine, and bromine.
Strychnine is a highly toxic, colorless, bitter, crystalline alkaloid used as a pesticide, particularly for killing small vertebrates such as birds and rodents. Strychnine, when inhaled, swallowed, or absorbed through the eyes or mouth, causes poisoning which results in muscular convulsions and eventually death through asphyxia. While it is no longer used medicinally, it was used historically in small doses to strengthen muscle contractions, such as a heart and bowel stimulant and performance-enhancing drug. The most common source is from the seeds of the Strychnos nux-vomica tree.
Jane Elizabeth Lathrop Stanford was an American philanthropist and co-founder of Stanford University in 1885, along with her husband, Leland Stanford, in memory of their only child, Leland Stanford Jr., who died of typhoid fever at age 15 in 1884. After her husband's death in 1893, she funded and operated the university almost single-handedly until her unsolved murder by strychnine poisoning in 1905.
Strychnos nux-vomica, the strychnine tree, also known as nux vomica, poison fruit, semen strychnos, and quaker buttons, is a deciduous tree native to India and to southeast Asia. It is a medium-sized tree in the family Loganiaceae that grows in open habitats. Its leaves are ovate and 5–9 centimetres (2–3.5 in) in size. It is known for being the natural source of the extremely poisonous compound strychnine.
Strychnos is a genus of flowering plants, belonging to the family Loganiaceae. The genus includes about 200 accepted species of trees and lianas. The genus is widely distributed around the world's tropics and is noted for the presence of poisonous indole alkaloids in the roots, stems and leaves of various species. Among these alkaloids are the well-known and virulent poisons strychnine and curare.
The Betti reaction is a chemical addition reaction of aldehydes, primary aromatic amines and phenols producing α-aminobenzylphenols.
The Jacobsen epoxidation, sometimes also referred to as Jacobsen-Katsuki epoxidation is a chemical reaction which allows enantioselective epoxidation of unfunctionalized alkyl- and aryl- substituted alkenes. It is complementary to the Sharpless epoxidation (used to form epoxides from the double bond in allylic alcohols). The Jacobsen epoxidation gains its stereoselectivity from a C2 symmetric manganese(III) salen-like ligand, which is used in catalytic amounts. The manganese atom transfers an oxygen atom from chlorine bleach or similar oxidant. The reaction takes its name from its inventor, Eric Jacobsen, with Tsutomu Katsuki sometimes being included. Chiral-directing catalysts are useful to organic chemists trying to control the stereochemistry of biologically active compounds and develop enantiopure drugs.
Lisofylline (LSF) is a synthetic small molecule with novel anti-inflammatory properties. LSF can effectively prevent type 1 diabetes in preclinical models and improves the function and viability of isolated or transplanted pancreatic islets. It is a metabolite of pentoxifylline.
Indole alkaloids are a class of alkaloids containing a structural moiety of indole; many indole alkaloids also include isoprene groups and are thus called terpene indole or secologanin tryptamine alkaloids. Containing more than 4100 known different compounds, it is one of the largest classes of alkaloids. Many of them possess significant physiological activity and some of them are used in medicine. The amino acid tryptophan is the biochemical precursor of indole alkaloids.
Strychnos spinosa, the Natal orange, also called Mokotra in Madagascar, is a tree indigenous to tropical and subtropical Africa. It produces sweet-sour, yellow fruits, containing numerous hard brown seeds. Greenish-white flowers grow in dense heads at the ends of branches. The fruits tend to appear only after good rains. It is related to the deadly Strychnos nux-vomica, which contains strychnine. The smooth, hard fruit are large and green, ripen to yellow colour. Inside the fruit are tightly packed seeds, which may be toxic, surrounded by a fleshy, brown, edible covering.
Strychnine poisoning is poisoning induced by strychnine. It can be fatal to humans and other animals and can occur by inhalation, swallowing or absorption through eyes or mouth. It produces some of the most dramatic and painful symptoms of any known toxic reaction, making it quite noticeable and a common choice for assassinations and poison attacks. For this reason, strychnine poisoning is often portrayed in literature and film, such as the murder mysteries written by Agatha Christie.
Strychnine total synthesis in chemistry describes the total synthesis of the complex biomolecule strychnine. The first reported method by the group of Robert Burns Woodward in 1954 is considered a classic in this research field.
DuPhos is a class of organophosphorus compound that are used ligands for asymmetric synthesis. The name DuPhos is derived from (1) the chemical company that sponsored the research leading to this ligand's invention, DuPont and (2) the compound is a diphosphine ligand type. Specifically it is classified as a C2-symmetric ligand, consisting of two phospholanes rings affixed to a benzene ring.
In chemistry, metal-catalysed hydroboration is a reaction used in organic synthesis. It is one of several examples of homogeneous catalysis.
Camphorsultam, also known as bornanesultam, is a crystalline solid primarily used as a chiral auxiliary in the synthesis of other chemicals with a specific desired stereoselectivity. Camphorsultam is commercially available in both enantiomers of its exo forms: (1R)-(+)-2,10-camphorsultam and (1S)-(−)-2,10-camphorsultam.
Strychnos madagascariensis, the black monkey orange, is an African tropical and sub-tropical tree belonging to the Loganiaceae family. It is a tree with characteristically large fruit but can confused with some other species of the genus.
Akuammicine is a monoterpene indole alkaloid of the Vinca sub-group. It is found in the Apocynaceae family of plants including Picralima nitida, Vinca minor and the Aspidosperma.
2-Methylbutanoic acid, also known as 2-methylbutyric acid is a branched-chain alkyl carboxylic acid with the chemical formula CH3CH2CH(CH3)CO2H, classified as a short-chain fatty acid. It exists in two enantiomeric forms, (R)- and (S)-2-methylbutanoic acid. (R)-2-methylbutanoic acid occurs naturally in cocoa beans and (S)-2-methylbutanoic occurs in many fruits such as apples and apricots, as well as in the scent of the orchid Luisia curtisii.
Strychnos icaja is a species belonging to the plant family Loganiaceae, native to West Tropical Africa. It is a very large, tropical rainforest liana which may attain a length of 100 m (330 ft).
Strychnos alkaloids are natural products primarily found in the seeds of the strychnine tree and in the genus catharanthus.