357-57-3 Usage
Description
10,11-Dimethoxystrychnine is a naturally occurring alkaloid compound found in the seeds of Strychnos nux-vomica L. and other Strychnos species. It possesses a unique chemical structure with two methoxy groups at the 10th and 11th positions, which contributes to its diverse pharmacological properties.
Uses
Used in Pharmaceutical Industry:
10,11-Dimethoxystrychnine is used as an antineoplastic agent for its potential anti-cancer properties. It has been found to exhibit cytotoxic and antiproliferative effects, making it a promising candidate for the development of cancer therapeutics.
Used in Chemical Industry:
10,11-Dimethoxystrychnine is used as a denaturing alcohol and lubricant additive. Its unique chemical properties make it suitable for these applications, where it can help improve the performance and stability of various products.
Used in Analytical Chemistry:
10,11-Dimethoxystrychnine is used for the colorimetric analysis of nitrates. Its ability to react with nitrates and produce a color change makes it a valuable tool in analytical chemistry for detecting and quantifying nitrate levels in various samples.
Used in Research:
10,11-Dimethoxystrychnine is used as a convulsant in research settings, particularly in the study of neurological disorders and the effects of seizures on the brain. Its ability to induce convulsions can help researchers better understand the mechanisms behind seizure disorders and develop potential treatments.
Air & Water Reactions
Slightly soluble in water.
Hazard
Poison by ingestion and inhalation.
Health Hazard
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.
Health Hazard
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.
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.
