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
[H][C@]12C[C@@]3([H])C4=CCO[C@@]5([H])CC(=O)N6C7=C(C=C(OC)C(OC)=C7)[C@@]1(CCN2C4)[C@]6([H])[C@@]35[H]
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 |
|---|---|---|
| Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. | 1991 Jan-Feb |
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| Construction and evaluation of ion selective electrodes for nitrate with a summing operational amplifier. Application to tobacco analysis. | 2001 Jan 5 |
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| Brucine and two solvates. | 2004 Dec |
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| Analysis of strychnine from detoxified Strychnos nux-vomica [corrected] seeds using liquid chromatography-electrospray mass spectrometry. | 2004 Jul |
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| Asparagine, valine, and threonine in the third extracellular loop of muscarinic receptor have essential roles in the positive cooperativity of strychnine-like allosteric modulators. | 2005 May |
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| Hydrogen bonding in brucinium dihydrogen citrate trihydrate at 130 K. | 2005 Nov |
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| Functional characterisation of human glycine receptors in a fluorescence-based high throughput screening assay. | 2005 Oct 3 |
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| Interaction studies of multiple binding sites on m4 muscarinic acetylcholine receptors. | 2006 Aug |
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| Rapid separation of strychnine and brucine on a dynamically modified poly(dimethylsiloxane) microchip followed by electrochemical detection. | 2006 Jan |
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| Analysis of Strychnos alkaloids in traditional Chinese medicines with improved sensitivity by sweeping micellar electrokinetic chromatography. | 2006 Jul 21 |
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| Identification of various allosteric interaction sites on M1 muscarinic receptor using 125I-Met35-oxidized muscarinic toxin 7. | 2006 May |
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| Separation and determination of strychnine and brucine in Strychnos nux-vomica L. and its preparation by nonaqueous capillary electrophoresis. | 2006 May 3 |
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| [Study on the interaction between brucine and bovine serum albumin]. | 2007 Apr |
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| Pseudopolymorphism in brucine: brucine-water (1/2), the third crystal hydrate of brucine. | 2007 Aug |
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| Application of high performance capillary electrophoresis on toxic alkaloids analysis. | 2007 Jun |
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| Preparation of liposomal brucine and its pharmaceutical/pharmacodynamic characterization. | 2007 Nov |
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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 Nov-Dec |
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| Allosteric modulation of muscarinic acetylcholine receptors. | 2007 Sep |
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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 Sep |
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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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| [Study on safety and pharmacodynamic action of transdermal liposomal brucine]. | 2008 Dec |
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| [Strychnos alkaloids inhibit the proliferation of adult rat neuroprogenitor cells]. | 2008 Dec |
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| Simultaneous determination of thirteen plant alkaloids in a human specimen by SPE and HPLC. | 2008 Jul |
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| [Study on transdermal absorption characteristics of brucine in vitro]. | 2008 Mar |
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| A simple method to identify the unprocessed Strychnos seeds used in herbal medicinal products. | 2008 Mar |
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| Supramolecular tilt chirality in crystals of steroids and alkaloids. | 2008 Mar |
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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 Nov 15 |
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| [Influencing factors in preparation of brucine liposomes by ammonium sulfate transmembrane gradients]. | 2008 Sep |
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| [Pharmaceutical characteristics of brucine stealth liposomes]. | 2008 Sep |
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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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| Micelle enhanced fluorimetric and thin layer chromatography densitometric methods for the determination of (+/-) citalopram and its S-enantiomer escitalopram. | 2009 Apr 7 |
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| Absolute configuration of 3,3'-diphenyl-[2,2'-binaphthalene]-1,1'-diol revisited. | 2009 Aug 7 |
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| [A comparative study on HPLC fingerprint of Semen Strychni and the processed]. | 2009 Dec |
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| Divergence of allosteric effects of rapacuronium on binding and function of muscarinic receptors. | 2009 Dec 28 |
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| Anti-proliferative and cytotoxic effects of Strychnos nux-vomica root extract on human multiple myeloma cell line - RPMI 8226. | 2009 Feb |
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| Determination of strychnine and brucine in rat plasma using liquid chromatography electrospray ionization mass spectrometry. | 2009 Feb 20 |
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| Ion pairing and salt structure in organic salts through diffusion, Overhauser, DFT and X-ray methods. | 2009 Jul 13 |
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| A three-phase microfluidic chip for rapid sample clean-up of alkaloids from plant extracts. | 2009 Jul 21 |
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| A rare case of brucine poisoning complicated by rhabdomyolysis and acute renal failure. | 2009 Jun |
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| Intestinal permeability of antitumor alkaloids from the processed seeds of Strychnos nux-vomica in a Caco-2 cell model. | 2009 May |
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| Preparative resolution of etodolac enantiomers by preferential crystallization method. | 2009 Oct |
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| Preparation and pharmaceutical/pharmacodynamic evaluation of topical brucine-loaded liposomal hydrogel. | 2009 Oct |
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| [Preparation and in vitro evaluation of brucine-loaded polylacticacid nanoparticles]. | 2009 Sep |
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| Prediction of functionally selective allosteric interactions at an M3 muscarinic acetylcholine receptor mutant using Saccharomyces cerevisiae. | 2010 Aug |
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| Rapid and sensitive determination of strychnine and brucine in human urine by capillary electrophoresis with field-amplified sample stacking. | 2010 Feb |
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| Death due to ingestion of nicotine-containing solution: case report and review of the literature. | 2010 Feb 25 |
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| Modified porphyrin-brucine conjugated to gold nanoparticles and their application in photodynamic therapy. | 2010 Jul 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 Mar |
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| Spectroscopic and physicochemical studies on organic crystal of brucine hydrogen maleate pentahydrate. | 2010 Sep 15 |
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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NCI_THESAURUS |
C221
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BRUCINE
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DTXSID2024662
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
