Brucine (CHEM002413)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (9)XML
Record Information
Version1.0
Creation Date2009-07-23 18:26:04 UTC
Update Date2026-03-26 21:22:19 UTC
Accession NumberCHEM002413
Identification
Common NameBrucine
ClassSmall Molecule
DescriptionBrucine is a plant toxin found in several species, most notably the Strychnine tree (Strychnos nux-vomica L.). Medically, brucine is primarily used in the regulation of high blood pressure and other comparatively benign cardiac ailments. (1)
Contaminant Sources
  • Clean Air Act Chemicals
  • HPV EPA Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Amine
  • Ether
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC23H26N2O4
Average Molecular Mass394.464 g/mol
Monoisotopic Mass394.189 g/mol
CAS Registry Number357-57-3
IUPAC Name4,5-dimethoxy-12-oxa-8,17-diazaheptacyclo[15.5.2.0¹,¹⁸.0²,⁷.0⁸,²².0¹¹,²¹.0¹⁵,²⁰]tetracosa-2(7),3,5,14-tetraen-9-one
Traditional Namebrucine
SMILESCOC1=CC2=C(C=C1OC)C13CCN4CC5=CCOC6CC(=O)N2C1C6C5CC34
InChI IdentifierInChI=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
InChI KeyRRKTZKIUPZVBMF-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as strychnos alkaloids. These are alkaloids having a core structure based on the strychnan, stemmadenine (seco-curan), or the akuammicine (curan) skeleton.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassStrychnos alkaloids
Sub ClassNot Available
Direct ParentStrychnos alkaloids
Alternative Parents
Substituents
  • Strychnan skeleton
  • Akuammicine-skeleton
  • Stemmadenine-skeleton
  • Carbazole
  • Quinolidine
  • Indole or derivatives
  • Indolizidine
  • Anisole
  • Alkyl aryl ether
  • Delta-lactam
  • Piperidinone
  • Aralkylamine
  • Piperidine
  • Benzenoid
  • N-alkylpyrrolidine
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Amino acid or derivatives
  • Lactam
  • Carboxamide group
  • Azacycle
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Ether
  • Dialkyl ether
  • Hydrocarbon derivative
  • Amine
  • Organopnictogen compound
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point178°C
Boiling PointNot Available
Solubility3.2 mg/mL at 15°C [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
Predicted Properties
PropertyValueSource
Water Solubility0.32 g/LALOGPS
logP1.85ALOGPS
logP0.61ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)17.24ChemAxon
pKa (Strongest Basic)8.85ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area51.24 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity107.43 m³·mol⁻¹ChemAxon
Polarizability41.98 ųChemAxon
Number of Rings7ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-0009000000-9ab15bf460468b70f928Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-01yo-0195000000-eae039134db6933f6076Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0009000000-73d742bb3c4eabe4901eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0002-0009000000-41fe1ffbf7c12ef45f6eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0009000000-b5d95786b28beaef339dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0009000000-8bc90ab344491204f55eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05nf-0039000000-f2335461f64375e40c9eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-7acb0d26429fdd209153Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0009000000-0f551d37cae34ddb3bb7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000g-3029000000-788a525198ca58efb2e9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0009000000-8d2cc2bffa4a115e5498Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0009000000-8d2cc2bffa4a115e5498Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002b-0009000000-dc32b4b2d0c882d4ad91Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-c89f5798c7f5c75bb99eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0009000000-90711b505cdaed4588aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0007-0009000000-b81cf979742604114b8cSpectrum
Toxicity Profile
Route of ExposureOral (ingestion) (4) ; dermal (4)
Mechanism of ToxicityBrucine acts as an antagonist at the inhibitory or strychnine-sensitive glycine receptor, a ligand-gated chloride channel in the spinal cord and the brain. (3)
MetabolismNot Available
Toxicity ValuesLD50: 4 mg/kg (Oral, Rat) (5) LD50: 91 mg/kg (Intraperitoneal, Rat) (5) LD50: 60 mg/kg (Subcutaneous, Rat) (5)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesBrucine is a plant toxin found in several species, most notably the Strychnine tree (Strychnos nux-vomica L.). Medically, brucine is primarily used in the regulation of high blood pressure and other comparatively benign cardiac ailments. (1)
Minimum Risk LevelNot Available
Health EffectsDeath may result from asphyxia or sheer exhaustion. (1)
SymptomsBrucine causes muscular convulsions of increasing intensity and frequency and eventually death through asphyxia or sheer exhaustion. (1)
TreatmentTreatment of brucine poisoning involves an oral application of an activated charcoal infusion to absorb any poison within the digestive tract that has not yet been absorbed into the blood. Anticonvulsants such as phenobarbital or diazepam are administered to control convulsions, along with muscle relaxants such as dantrolene to combat muscle rigidity. (2)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0249406
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00001695
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBrucine
Chemspider ID191250
ChEBI IDNot Available
PubChem Compound ID220520
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available