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 |
|||
Target ID: CHEMBL614245 |
|||
Target ID: CHEMBL614721 |
|||
Target ID: CHEMBL614102 |
|||
Target ID: CHEMBL279 |
|||
Target ID: GO:0042098 |
|||
Target ID: CHEMBL2366315 |
|||
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 |
|||
| Primary | Unknown Approved UseUnknown |
|||
| 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 |
|
| Subtype-selective positive cooperative interactions between brucine analogs and acetylcholine at muscarinic receptors: functional studies. | 1999 Apr |
|
| Effects of brucine, a plant alkaloid, on M(1) muscarinic receptors and alpha(1)-adrenoceptors in the rabbit vas deferens preparation. | 2001 Apr |
|
| Nitric oxide and chronic HCV and HIV infections. | 2001 May |
|
| Herbal medicine causing likely strychnine poisoning. | 2002 Aug |
|
| Asymmetric carbon-carbon coupling of phenols or anilines with aryllead triacetates. | 2002 May 15 |
|
| Quantitative analysis of strychnine and Brucine in Strychnos nux-vomica using 1H-NMR. | 2003 Dec |
|
| Bisquaternary dimers of strychnine and brucine. A new class of potent enhancers of antagonist binding to muscarinic M2 receptors. | 2003 Jun 12 |
|
| Comparison of the responses of the chorda tympani and glossopharyngeal nerves to taste stimuli in C57BL/6J mice. | 2003 Mar 4 |
|
| Analgesic and anti-inflammatory properties of brucine and brucine N-oxide extracted from seeds of Strychnos nux-vomica. | 2003 Oct |
|
| Analysis of strychnine and brucine in postmortem specimens by RP-HPLC: a case report of fatal intoxication. | 2004 Mar |
|
| On-chip potential gradient detection with a portable capillary electrophoresis system. | 2004 Mar |
|
| Functional characterisation of the human alpha1 glycine receptor in a fluorescence-based membrane potential assay. | 2004 May 1 |
|
| New PVC nitrate-selective electrode: application to vegetables and mineral waters. | 2005 Jan 26 |
|
| Functional characterisation of human glycine receptors in a fluorescence-based high throughput screening assay. | 2005 Oct 3 |
|
| Analysis of strychnos alkaloids using electrospray ionization Fourier transform ion cyclotron resonance multi-stage tandem mass spectrometry. | 2006 |
|
| Rapid separation of strychnine and brucine on a dynamically modified poly(dimethylsiloxane) microchip followed by electrochemical detection. | 2006 Jan |
|
| Analysis of Strychnos alkaloids in traditional Chinese medicines with improved sensitivity by sweeping micellar electrokinetic chromatography. | 2006 Jul 21 |
|
| Separation and determination of strychnine and brucine in Strychnos nux-vomica L. and its preparation by nonaqueous capillary electrophoresis. | 2006 May 3 |
|
| [Study on the interaction between brucine and bovine serum albumin]. | 2007 Apr |
|
| Pseudopolymorphism in brucine: brucine-water (1/2), the third crystal hydrate of brucine. | 2007 Aug |
|
| Preparation of liposomal brucine and its pharmaceutical/pharmacodynamic characterization. | 2007 Nov |
|
| Allosteric modulation of muscarinic acetylcholine receptors. | 2007 Sep |
|
| [Study on safety and pharmacodynamic action of transdermal liposomal brucine]. | 2008 Dec |
|
| [Strychnos alkaloids inhibit the proliferation of adult rat neuroprogenitor cells]. | 2008 Dec |
|
| Simultaneous determination of thirteen plant alkaloids in a human specimen by SPE and HPLC. | 2008 Jul |
|
| Glycine and glycine receptor signalling in non-neuronal cells. | 2009 |
|
| Pro370Leu mutant myocilin impairs mitochondrial functions in human trabecular meshwork cells. | 2009 |
|
| Absolute configuration of 3,3'-diphenyl-[2,2'-binaphthalene]-1,1'-diol revisited. | 2009 Aug 7 |
|
| Anti-proliferative and cytotoxic effects of Strychnos nux-vomica root extract on human multiple myeloma cell line - RPMI 8226. | 2009 Feb |
|
| [Preparation and in vitro evaluation of brucine-loaded polylacticacid nanoparticles]. | 2009 Sep |
|
| Prediction of functionally selective allosteric interactions at an M3 muscarinic acetylcholine receptor mutant using Saccharomyces cerevisiae. | 2010 Aug |
|
| Modified porphyrin-brucine conjugated to gold nanoparticles and their application in photodynamic therapy. | 2010 Jul 21 |
|
| 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
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
NCI_THESAURUS |
C221
Created by
admin on Fri Dec 15 15:09:13 GMT 2023 , Edited by admin on Fri Dec 15 15:09:13 GMT 2023
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
m2734
Created by
admin on Fri Dec 15 15:09:13 GMT 2023 , Edited by admin on Fri Dec 15 15:09:13 GMT 2023
|
PRIMARY | Merck Index | ||
|
2181419
Created by
admin on Fri Dec 15 15:09:13 GMT 2023 , Edited by admin on Fri Dec 15 15:09:13 GMT 2023
|
PRIMARY | |||
|
757797
Created by
admin on Fri Dec 15 15:09:13 GMT 2023 , Edited by admin on Fri Dec 15 15:09:13 GMT 2023
|
PRIMARY | |||
|
307
Created by
admin on Fri Dec 15 15:09:13 GMT 2023 , Edited by admin on Fri Dec 15 15:09:13 GMT 2023
|
PRIMARY | |||
|
6NG17YCK6H
Created by
admin on Fri Dec 15 15:09:13 GMT 2023 , Edited by admin on Fri Dec 15 15:09:13 GMT 2023
|
PRIMARY | |||
|
C083806
Created by
admin on Fri Dec 15 15:09:13 GMT 2023 , Edited by admin on Fri Dec 15 15:09:13 GMT 2023
|
PRIMARY | |||
|
C87455
Created by
admin on Fri Dec 15 15:09:13 GMT 2023 , Edited by admin on Fri Dec 15 15:09:13 GMT 2023
|
PRIMARY | |||
|
357-57-3
Created by
admin on Fri Dec 15 15:09:13 GMT 2023 , Edited by admin on Fri Dec 15 15:09:13 GMT 2023
|
PRIMARY | |||
|
442021
Created by
admin on Fri Dec 15 15:09:13 GMT 2023 , Edited by admin on Fri Dec 15 15:09:13 GMT 2023
|
PRIMARY | |||
|
206-614-7
Created by
admin on Fri Dec 15 15:09:13 GMT 2023 , Edited by admin on Fri Dec 15 15:09:13 GMT 2023
|
PRIMARY | |||
|
BRUCINE
Created by
admin on Fri Dec 15 15:09:13 GMT 2023 , Edited by admin on Fri Dec 15 15:09:13 GMT 2023
|
PRIMARY | |||
|
DTXSID2024662
Created by
admin on Fri Dec 15 15:09:13 GMT 2023 , Edited by admin on Fri Dec 15 15:09:13 GMT 2023
|
PRIMARY |
ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
