357-57-3 Usage
Description
As a Chinese medicine, brucine was firstly recorded in Compendium of Materia
Medica. The Chinese name for brucine is “Maqian” because it looks like ancient
coins with horse icon, where “Ma” refers to “horse” and “qian” refers to “coins.”
This traditional Chinese herb has cold, bitter, and toxic properties. It can be used to
treat typhoid fever, throat pain, and lumps. Brucine is mainly extracted from the
traditional Chinese medicine “Maqian.” In 1819, Pelletier and Caventou firstly isolated the alkaline brucine from the seeds and bark of Strychnos nux-vomica
L.?Brucine is the dry and mature seeds of Loganiaceae Evergreen tree plants including Strychnos nux-vomica L. and Strychnos pierriana A.W. Hill.
Chemical Properties
White powder
Physical properties
Appearance: white crystalline powder; tastes very bitter. Solubility: slightly soluble
in water; soluble in ether, chloroform, ethanol, methanol, and other organic solvents
. Melting point: 175–178?°C. Specific optical rotation: ?118°.
Uses
Different sources of media describe the Uses of 357-57-3 differently. You can refer to the following data:
1. Brucine is used as a denaturing alcohol, lubricant additive, separation of racemic mixtures. Proposed to reduce inflammatory mediators including COX-2, PGE2 and thromboxane B2. Able to induce cell apoptosis, with cytotoxic and antiproliferative effects.
2. Brucine occurs in the seeds of strychnosspecies (Strychnos nux vomica L. and otherspecies). It is used for denaturing alcoholsand oils; for separating racemic mixtures;and as an additive to lubricants. It is alsoused for colorimetric analysis of nitrate.Therapeutically, it is used as a stimulant.
3. 10,11-Dimethoxystrychnine can be used for antineoplastic, convulsant.
General Description
A white crystalline solid. Combustible but may require some effort to ignite. Toxic by inhalation (vapor, dust, etc.) and ingestion.
Air & Water Reactions
Slightly soluble in water.
Hazard
Poison by ingestion and inhalation.
Health Hazard
Different sources of media describe the Health Hazard of 357-57-3 differently. You can refer to the following data:
1. The toxicity of brucine is similar to that ofstrychnine. It is a very poisonous alkaloid. Itis a strong convulsant; excites all portions ofthe central nervous system. Toxic symptomsinclude headache, tremor, muscular rigidity,and convulsions. Death may occur fromrespiratory arrest after a few convulsions.LD50 value, subcutaneous (mice): 60 mg/kg.
2. Chemical is toxic if inhaled, swallowed, or absorbed through skin. Inhalation produces intense bitter taste. Ingestion causes nausea, vomiting, restlessness, excitement, twitching, and (rarely) convulsions. Contact with dust irritates eyes.
Agricultural Uses
Rodenticide: Used in the manufacture of other chemicals, in perfumes,
as a medication for animals, and as a poison for rodents
Trade name
DOLCO MOUSE CEREAL?; PIED
PIPER MOUSE SEED? (Brucine)
Pharmacology
1. Analgesic effects: Brucine is reported to exert analgesic effects through both
central and peripheral pathways. Possible mechanisms of the analgesic effects
include blocking the voltage-gated sodium channel, inhibiting the synthesis of
PGE2, acting on the adrenergic receptor and the L-arginine-NO pathway. Brucine
(0.48?mg/kg) can significantly elevate the pain threshold in mice.2. Anti-tumor effects: Studies have shown that brucine inhibits the cell proliferation in breast cancer, liver cancer, leukemia, and Ehrlich ascites tumors by inducing tumor cell apoptosis, inhibiting angiogenesis, reversing tumor multidrug
resistance, and regulating the expression of various cytokines. In addition, at the
dose of 320?μg/ml, the in?vitro hepatocarcinoma cell growth inhibition rate of
brucine is nearly 100%.3. Anti-pathogen effects: In vitro study shows that 0.1% brucine can completely
inhibit the growth of Haemophilus influenzae, Streptococcus pneumoniae, and
alpha Streptococcus and Mlicrococcus catarrhalis. At the dose of 500?μg/ml, the
inhibitory rate of brucine on human immunodeficiency virus reverse transcriptase is above 30%.4. Other pharmacological effects: Anti-inflammation, regulation of the immune
system, regulation of the cardiovascular system, antitussive, expectorant, and
antiasthenic and antibacterial effects.
Clinical Use
The applications of brucine include reducing swelling; resolving mass; activating
meridians to stop pain; attenuating rheumatism, stubborn paralysis, and numbness
paralysis; alleviating bruises; etc. It has been used for nearly a thousand years and
achieved prominent clinical efficacy. In the clinical practice, brucine is used as a
compatibility prescription or compound medicine in treating rheumatism, rheumatoid arthritis, stroke hemiplegia, dementia, retinopathy, and orthopedic and other
surgical diseases.Brucine is the main active ingredient in Strychnos and plays an important role in
treating diseases. However, brucine is also a toxic ingredient, which limits the scope
of its clinical application. Further studies of its pharmacological effects and toxicity
will improve its clinical application.
Safety Profile
A poison by
subcutaneous, intravenous, and
intraperitoneal routes. An alkaloid-like
strychnine, but one-sixth as toxic. When
heated to decomposition it emits toxic
fumes of Nx,. See also STRYCHNINE
Purification Methods
Crystallise brucine once from water or aqueous Me2CO (as the tetrahydrate), then suspend it in CHCl3 and shake with anhydrous Na2SO4 (to dehydrate the brucine, which then dissolves). Precipitate it by pouring the solution into a large bulk of dry pet ether (b 40-60o), filter and heat to 120o in a high vacuum [Turner J Chem Soc 842 1951]. The tetrahydrate crystallises from a mixture of EtOH and H2O as colourless elongated needles [Eeles Acta Cryst 6 809 1953, Beilstein 27 III/IV 7875.] VERY POISONOUS
Check Digit Verification of cas no
The CAS Registry Mumber 357-57-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,5 and 7 respectively; the second part has 2 digits, 5 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 357-57:
(5*3)+(4*5)+(3*7)+(2*5)+(1*7)=73
73 % 10 = 3
So 357-57-3 is a valid CAS Registry Number.
InChI:InChI=1/C23H26N2O4/c1-27-16-8-14-15(9-17(16)28-2)25-20(26)10-18-21-13-7-19-23(14,22(21)25)4-5-24(19)11-12(13)3-6-29-18/h3,8-9,13,18-19,21-22H,4-7,10-11H2,1-2H3
357-57-3Relevant articles and documents
Lewis acid-promoted electron transfer deoxygenation of epoxides, sulfoxides, and amine N-oxides: the role of low-valent niobium complexes from NbCl5 and Zn
Oh, Kyungsoo,Knabe, William Eric
experimental part, p. 2966 - 2974 (2009/05/30)
A mild and operationally simple deoxygenation of epoxides, sulfoxides, and amine N-oxides is described using a sub-stoichiometric amount of low-valent niobium complexes generated in situ from commercially available NbCl5 and zinc dust. The deoxygenation proceeds by a reductive cleavage of polarized O-C/O-N/O-S bonds through a single electron transfer from zinc metal to the niobium-substrate complex due to the high oxophilic nature of the niobium species. The presence of adjacent radical-stabilizing groups is beneficial to epoxide substrates; however the similar prerequisite does not apply to sulfoxides and amine N-oxides, where a broad range of substrates are efficiently deoxygenated in excellent yields.
Application of Host-Guest Complexation Method to Isolation of Natural Product
Segawa, Mari,Mori, Koji,Toda, Fumio
, p. 1755 - 1758 (2007/10/02)
Application of host-guest complexation method to isolation of caffeine, nicotine, and cholesterol fom tea and tabaco leaves, and gallstone, respectively, has been reported.Separations of strychnine and brucine, and sparteine and brucine by the same method were also reported.
Substituted dodecahydrotriphenylenes, decahydro-1H-cyclopenta[1]phenanthrenes, decahydro-1H-pyrido[1,2-f]phenanthridines and decahydropyrrolo[1,2-f]phenanthridines as CNS agents
-
, (2008/06/13)
1,2,3,4,4a,4b,5,6,7,8,8a,12b-Dodecahydro-7-(oxo, hydroxy or amino)-9-hydroxy-11-(alkyl, alkoxy or alkoxyalkyl)triphenylenes, 2,3,3a,3b,4,5,6,7,7a,11b-decahydro-6-(oxo, hydroxy or amino)-8-hydroxy-10-(alkyl, alkoxy or alkoxyalkyl)-1H-cyclopenta[1]phenanthrenes, 2,3,4,4a,4b,5,6,7,8,8a-decahydro-7-(oxo, hydroxy or amino)-9-hydroxy-11-(alkyl, alkoxy, alkoxyalkyl, aralkyl, aralkoxy, aryloxyalkyl or aralkoxyalkyl)-1H-pyrido[1,2-f]phenanthridines, and 1,2,3,3a,3b,4,5,6,7,7a-decahydro-6-(oxo, hydroxy or amino)-8-hydroxy-10-(alkyl, alkoxy or alkoxyalkyl)pyrrolo[1,2-f]phenanthridines and derivatives are valuable as central nervous system active agents or as intermediates to compounds having such activity.
