Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C23H26N2O4 |
| Molecular Weight | 394.4635 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 6 / 6 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC2=C(C=C1OC)[C@@]34CCN5CC6=CCO[C@H]7CC(=O)N2[C@H]3[C@H]7[C@H]6C[C@@H]45
InChI
InChIKey=RRKTZKIUPZVBMF-IBTVXLQLSA-N
InChI=1S/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/t13-,18-,19-,21-,22-,23+/m0/s1
DescriptionCurator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/21513620
https://www.ncbi.nlm.nih.gov/pubmed/23500380
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/21513620
https://www.ncbi.nlm.nih.gov/pubmed/23500380
Brucine is an alkaloid resembling strychnine but it is much less potent than strychnine. Brucine was first discovered in 1819 by Pelletier and Caventou in the bark of the Strychnos nux vomica tree. Brucine causes paralysis of the peripheral nerve endings and produces violent convulsions. Since brucine is a large chiral molecule, it has been used as an enantioselective recognition agent using in chiral resolution. While brucine has been shown to have good anti-tumor effects, on both hepatocellular carcinoma and breast cancer, 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, as well as in some Ayurveda and homeopathy drugs. Like strychnine, brucine also functions as antagonist at the glycine receptor and paralyzes the inhibitory neurons
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL615021 |
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Target ID: CHEMBL614245 |
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Target ID: CHEMBL614721 |
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Target ID: CHEMBL614102 |
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Target ID: CHEMBL279 |
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Target ID: GO:0042098 |
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Target ID: CHEMBL2366315 |
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Target ID: CHEMBL5845 |
1.7 µM [Ki] | ||
Target ID: CHEMBL2363052 |
1.4 µM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Spectroscopic and physicochemical studies on organic crystal of brucine hydrogen maleate pentahydrate. | 2010-09-15 |
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| Prediction of functionally selective allosteric interactions at an M3 muscarinic acetylcholine receptor mutant using Saccharomyces cerevisiae. | 2010-08 |
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| Modified porphyrin-brucine conjugated to gold nanoparticles and their application in photodynamic therapy. | 2010-07-21 |
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| Ammonium sulfate gradient loading of brucine into liposomes: effect of phospholipid composition on entrapment efficiency and physicochemical properties in vitro. | 2010-03 |
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| Death due to ingestion of nicotine-containing solution: case report and review of the literature. | 2010-02-25 |
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| Rapid and sensitive determination of strychnine and brucine in human urine by capillary electrophoresis with field-amplified sample stacking. | 2010-02 |
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| Divergence of allosteric effects of rapacuronium on binding and function of muscarinic receptors. | 2009-12-28 |
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| [A comparative study on HPLC fingerprint of Semen Strychni and the processed]. | 2009-12 |
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| Preparative resolution of etodolac enantiomers by preferential crystallization method. | 2009-10 |
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| Preparation and pharmaceutical/pharmacodynamic evaluation of topical brucine-loaded liposomal hydrogel. | 2009-10 |
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| [Preparation and in vitro evaluation of brucine-loaded polylacticacid nanoparticles]. | 2009-09 |
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| Absolute configuration of 3,3'-diphenyl-[2,2'-binaphthalene]-1,1'-diol revisited. | 2009-08-07 |
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| A three-phase microfluidic chip for rapid sample clean-up of alkaloids from plant extracts. | 2009-07-21 |
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| Ion pairing and salt structure in organic salts through diffusion, Overhauser, DFT and X-ray methods. | 2009-07-13 |
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| A rare case of brucine poisoning complicated by rhabdomyolysis and acute renal failure. | 2009-06 |
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| Intestinal permeability of antitumor alkaloids from the processed seeds of Strychnos nux-vomica in a Caco-2 cell model. | 2009-05 |
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| Micelle enhanced fluorimetric and thin layer chromatography densitometric methods for the determination of (+/-) citalopram and its S-enantiomer escitalopram. | 2009-04-07 |
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| Determination of strychnine and brucine in rat plasma using liquid chromatography electrospray ionization mass spectrometry. | 2009-02-20 |
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| Anti-proliferative and cytotoxic effects of Strychnos nux-vomica root extract on human multiple myeloma cell line - RPMI 8226. | 2009-02 |
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| Glycine and glycine receptor signalling in non-neuronal cells. | 2009 |
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| Pro370Leu mutant myocilin impairs mitochondrial functions in human trabecular meshwork cells. | 2009 |
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| [Study on safety and pharmacodynamic action of transdermal liposomal brucine]. | 2008-12 |
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| [Strychnos alkaloids inhibit the proliferation of adult rat neuroprogenitor cells]. | 2008-12 |
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| Simultaneous determination of five toxic alkaloids in body fluids by high-performance liquid chromatography coupled with electrospray ionization tandem mass spectrometry. | 2008-11-15 |
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| [Influencing factors in preparation of brucine liposomes by ammonium sulfate transmembrane gradients]. | 2008-09 |
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| [Pharmaceutical characteristics of brucine stealth liposomes]. | 2008-09 |
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| Simultaneous determination of thirteen plant alkaloids in a human specimen by SPE and HPLC. | 2008-07 |
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| [Study on transdermal absorption characteristics of brucine in vitro]. | 2008-03 |
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| A simple method to identify the unprocessed Strychnos seeds used in herbal medicinal products. | 2008-03 |
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| Supramolecular tilt chirality in crystals of steroids and alkaloids. | 2008-03 |
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| Final report of the safety assessment of Alcohol Denat., including SD Alcohol 3-A, SD Alcohol 30, SD Alcohol 39, SD Alcohol 39-B, SD Alcohol 39-C, SD Alcohol 40, SD Alcohol 40-B, and SD Alcohol 40-C, and the denaturants, Quassin, Brucine Sulfate/Brucine, and Denatonium Benzoate. | 2008 |
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| Development and validation of a TLC-densitometric method for the simultaneous quantitation of strychnine and brucine from Strychnos spp. and its formulations. | 2007-12-15 |
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| Preparation of liposomal brucine and its pharmaceutical/pharmacodynamic characterization. | 2007-11 |
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| Allosteric modulation of muscarinic acetylcholine receptors. | 2007-09 |
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| The cytotoxicity induced by brucine from the seed of Strychnos nux-vomica proceeds via apoptosis and is mediated by cyclooxygenase 2 and caspase 3 in SMMC 7221 cells. | 2007-09 |
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| Pseudopolymorphism in brucine: brucine-water (1/2), the third crystal hydrate of brucine. | 2007-08 |
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| Application of high performance capillary electrophoresis on toxic alkaloids analysis. | 2007-06 |
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| [Paharmacological mechanisms of cellular immunity of overall alkali of tongbiling for the treatment of joint destruction]. | 2007-06 |
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| [Study on the interaction between brucine and bovine serum albumin]. | 2007-04 |
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| Hollow fiber-based liquid-phase microextraction combined with on-line sweeping for trace analysis of Strychnos alkaloids in urine by micellar electrokinetic chromatography. | 2007-03-02 |
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| Isomorphous brucinium 4-nitrobenzoate methanol solvate and brucinium 4-nitrobenzoate dihydrate. | 2007-02 |
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| Electrochemical study of brucine on an electrode modified with magnetic carbon-coated nickel nanoparticles. | 2007-02 |
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| The effect of nifedipine on oral contraceptive-induced hypertension in rats. | 2006-12 |
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| Diffusion coefficient distribution from NMR-DOSY experiments using Hopfield neural network. | 2006-09 |
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| Brucinium 3,5-dinitrobenzoate methanol solvate, methanol disolvate and trihydrate. | 2006-08 |
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| Analysis of Strychnos alkaloids in traditional Chinese medicines with improved sensitivity by sweeping micellar electrokinetic chromatography. | 2006-07-21 |
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| [Studies on quality control methods of nuxvomica]. | 2006-02 |
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| Determinants of positive cooperativity between strychnine-like allosteric modulators and N-methylscopolamine at muscarinic receptors. | 2006 |
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| Construction and evaluation of ion selective electrodes for nitrate with a summing operational amplifier. Application to tobacco analysis. | 2001-01-05 |
|
| Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. | 1991-01-01 |
Patents
Sample Use Guides
three transdermal doses (10, 20 and 40 mg/kg) were administered to mice to evaluate pharmacological activity
Route of Administration:
Transdermal
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C221
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BRUCINE
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DTXSID2024662
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
